18.2.16 Carbon Dioxide, Carbonyl Sulfide, Carbon Disulfide, Isocyanates, Isothiocyanates, Carbodiimides, and Their Selenium, Tellurium, and Phosphorus Analogues (Update 2014)

Abstract

This chapter is an update to the earlier Science of Synthesis contribution (Section 18.2) describing methods for the synthesis and synthetic application of heterocumulenes (X=C=Y) with particular emphasis on supercritical carbon dioxide as a reaction medium for organic synthesis. It focuses on the literature published in the period 2002–2013.

Key words

carbon dioxide - supercritical carbon dioxide - carbonyl sulfide - carbon disulfide - carbonyl selenide - isocyanates - isothiocyanates - isoselenocyanates - carbodiimides

• 1 Jiang H, Jia L, Li J. Green Chem. 2000; 2: 161

• 2 Caravati M, Grunwaldt J.-D, Baiker A. Appl. Catal., A 2006; 298: 50

• 3 Yazdi AV, Beckman EJ. Ind. Eng. Chem. Res. 1997; 36: 2368

• 4 Wagner K.-D, Dahmen N, Dinjus E. J. Chem. Eng. Data 2000; 45: 672

• 5 Raveendran P, Wallen SL. J. Am. Chem. Soc. 2002; 124: 7274

• 6 Potluri VK, Xu J, Enick R, Beckman E, Hamilton AD. Org. Lett. 2002; 4: 2333

• 7 Montilla F, Rosa V, Prevett C, Avilés T, da Ponte MN, Masi D, Mealli C. J. Chem. Soc., Dalton Trans. 2003; 2170

• 8 Saffarzadeh-Matin S, Chuck CJ, Kerton FM, Rayner CM. Organometallics 2004; 23: 5176

• 9 Fürstner A, Koch D, Langemann K, Leitner W, Six C. Angew. Chem. Int. Ed. Engl. 1997; 36: 2466

• 10 Banister JA, Lee PD, Poliakoff M. Organometallics 1995; 14: 3876

• 11 Caravati M, Grunwaldt J.-D, Baiker A. Phys. Chem. Chem. Phys. 2005; 7: 278

• 12 Schneider MS, Grunwaldt J.-D, Baiker A. Langmuir 2004; 20: 2890

• 13 Grunwaldt J.-D, Caravati M, Ramin M, Baiker A. Catal. Lett. 2003; 90: 221

• 14 Steele AM, Zhu J, Tsang SC. Catal. Lett. 2001; 73: 9

• 15 Wang J.-Q, He L.-N, Miao C.-X. Green Chem. 2009; 11: 1013

• 16 Jenzer G, Schneider MS, Wandeler R, Mallat T, Baiker A. J. Catal. 2001; 199: 141

• 17 Gläser R, Jos R, Williardt J. Top. Catal. 2003; 22: 31

• 18 Hou Z, Theyssen N, Brinkmann A, Leitner W. Angew. Chem. Int. Ed. 2005; 44: 1346

• 19 González-Núñez ME, Mello R, Olmos A, Asensio G. J. Org. Chem. 2006; 71: 6432

• 20 Loeker F, Leitner W. Chem.–Eur. J. 2000; 6: 2011

• 21 Haas GR, Kolis JW. Organometallics 1998; 17: 4454

• 22 Haas GR, Kolis JW. Tetrahedron Lett. 1998; 39: 5923

• 23 Pesiri DR, Morita DK, Tumas W, Glaze W. Chem. Commun. (Cambridge) 1998; 1015

• 24 Wang J.-Q, Cai F, Wang E, He L.-N. Green Chem. 2007; 9: 882

• 25 Jia L, Jiang H, Li J. Chem. Commun. (Cambridge) 1999; 985

• 26 Wang Z.-Y, Jiang H.-F, Qi C.-R, Wang Y.-G, Dong Y.-S, Liu H.-L. Green Chem. 2005; 7: 582

• 27 Li J, Jiang H. Chem. Commun. (Cambridge) 1999; 2369

• 28 Oakes RS, Clifford AA, Bartle KD, Thornton-Pett M, Rayner CM. Chem. Commun. (Cambridge) 1999; 247

• 29 Campestrini S, Tonellato U. J. Mol. Catal. A: Chem. 2000; 164: 263

• 30 Hitzler MG, Poliakoff M. Chem. Commun. (Cambridge) 1997; 1667

• 31 Liu R, Zhao F, Fujita S.-i, Arai M. Appl. Catal., A 2007; 316: 127

• 32 Fujita S.-i, Akihara S, Zhao F, Liu R, Hasegawa M, Arai M. J. Catal. 2005; 236: 101

• 33 Fujita S.-i, Akihara S, Arai M. J. Mol. Catal. A: Chem. 2006; 249: 223

• 34 Zhao F, Fujita S.-i, Sun J, Ikushima Y, Arai M. Chem. Commun. (Cambridge) 2004; 2326

• 35 Zhao F, Ikushima Y, Shirai M, Ebina T, Arai M. J. Mol. Catal. A: Chem. 2002; 180: 259

• 36 Bhanage BM, Ikushima Y, Shirai M, Arai M. Catal. Lett. 1999; 62: 175

• 37 Li G, Jiang H, Li J. Green Chem. 2001; 3: 250

• 38 Chatterjee M, Chatterjee A, Ikushima Y. Green Chem. 2004; 6: 114

• 39 Pillai UR, Sahle-Demessie E, Young D. Appl. Catal., B 2003; 43: 131

• 40 Zhao F, Ikushima Y, Arai M. Catal. Today 2004; 93-95: 439

• 41 Zhao F, Ikushima Y, Arai M. Green Chem. 2003; 5: 656

• 42 Hiyoshi N, Rode CV, Sato O, Masuda Y, Yamaguchi A, Shirai M. Chem. Lett. 2008; 37: 734

• 43 Hiyoshi N, Osada M, Rode CV, Sato O, Shirai M. Appl. Catal., A 2007; 331: 1

• 44 Mine E, Hiyoshi N, Sato O, Rode CV, Shirai M. Chem. Lett. 2006; 35: 780

• 45 Hiyoshi N, Rode CV, Sato O, Shirai M. Appl. Catal., A 2005; 288: 43

• 46 Hiyoshi N, Rode CV, Sato O, Shirai M. J. Jpn. Pet. Inst. 2004; 47: 410

• 47 Hiyoshi N, Bando KK, Sato O, Yamaguchi A, Rode CV, Shirai M. Catal. Commun. 2009; 10: 1702

• 48 Hiyoshi N, Rode CV, Sato O, Tetsuka H, Shirai M. J. Catal. 2007; 252: 57

• 49 Rode CV, Joshi UD, Sato O, Shirai M. Chem. Commun. (Cambridge) 2003; 1960

• 50 Wang H, Zhao F. Int. J. Mol. Sci. 2007; 8: 628

• 51 Sato T, Sato O, Arai K, Mine E, Hiyoshi N, Rode CV, Shirai M. J. Supercrit. Fluids 2006; 37: 87

• 52 Hiyoshi N, Mine E, Rode CV, Sato O, Ebina T, Shirai M. Chem. Lett. 2006; 35: 1060

• 53 Ichikawa S, Tada M, Iwasawa Y, Ikariya T. Chem. Commun. (Cambridge) 2005; 924

• 54 Rathke JW, Klingler RJ, Krause TR. Organometallics 1991; 10: 1350

• 55 Guo Y, Akgerman A. Ind. Eng. Chem. Res. 1997; 36: 4581

• 56 Sellin MF, Bach I, Webster JM, Montilla F, Rosa V, Avilés T, Poliakoff M, Cole-Hamilton DJ. J. Chem. Soc., Dalton Trans. 2002; 4569

• 57 Sellin MF, Webb PB, Cole-Hamilton DJ. Chem. Commun. (Cambridge) 2001; 781

• 58 Frisch AC, Webb PB, Zhao G, Muldoon MJ, Pogorzelec PJ, Cole-Hamilton DJ. Dalton Trans. 2007; 5531

• 59 Fujita S.-i, Akihara S, Fujisawa S, Arai M. J. Mol. Catal. A: Chem. 2007; 268: 244

• 60 Francio G, Wittmann K, Leitner W. J. Organomet. Chem. 2001; 621: 130

• 61 Hu Y, Chen W, Osuna AMB, Iggo JA, Xiao J. Chem. Commun. (Cambridge) 2002; 788

• 62 Wittmann K, Wisniewski W, Mynott R, Leitner W, Kranemann CL, Rische T, Eilbracht P, Kluwer S, Ernsting JM, Elsevier CJ. Chem.–Eur. J. 2001; 7: 4584

• 63 Rose PM, Clifford AA, Rayner CM. Chem. Commun. (Cambridge) 2002; 968

• 64 Parratt AJ, Adams DJ, Clifford AA, Rayner CM. Chem. Commun. (Cambridge) 2004; 2720

• 65 Hitzler MG, Smail FR, Poliakoff M, Ross SK. Chem. Commun. (Cambridge) 1998; 359

• 66 Amandi R, Hyde JR, Ross SK, Lotz TJ, Poliakoff M. Green Chem. 2005; 7: 288

• 67 Nishikido J, Kamishima M, Matsuzawa H, Mikami K. Tetrahedron 2002; 58: 8345

• 68 Kamalakar G, Komura K, Sugi Y. Appl. Catal., A 2006; 310: 155

• 69 Kamalakar G, Komura K, Sugi Y. Ind. Eng. Chem. Res. 2006; 45: 6118

• 70 Kamalakar G, Komura K, Sugi Y. Catal. Lett. 2006; 108: 31

• 71 Kamalakar G, Komura K, Sugi Y. Chem. Lett. 2005; 34: 1446

• 72 Komoto I, Kobayashi S. Org. Lett. 2002; 4: 1115

• 73 Morita DK, David SA, Tumas W, Pesiri DR, Glaze WH. Chem. Commun. (Cambridge) 1998; 1397

• 74 Early TR, Gordon RS, Carroll MA, Holmes AB, Shute RE, McConvey IF. Chem. Commun. (Cambridge) 2001; 1966

• 75 Carroll MA, Holmes AB. Chem. Commun. (Cambridge) 1998; 1395

• 76 Osswald T, Schneider S, Wang S, Bannwarth W. Tetrahedron Lett. 2001; 42: 2965

• 77 Shezad N, Oakes RS, Clifford AA, Rayner CM. Tetrahedron Lett. 1999; 40: 2221

• 78 Shezad N, Oakes RS, Clifford AA, Rayner CM. Chem. Ind. (Dekker) 2001; 82: 459

• 79 Shezad N, Clifford AA, Rayner CM. Tetrahedron Lett. 2001; 42: 323

• 80 Yeung LK, Lee Jr CT, Johnston KP, Crooks RM. Chem. Commun. (Cambridge) 2001; 2290

• 81 Bhanage BM, Ikushima Y, Shirai M, Arai M. Tetrahedron Lett. 1999; 40: 6427

• 82 Gordon RS, Holmes AB. Chem. Commun. (Cambridge) 2002; 640

• 83 Kuchurov IV, Vasil’ev AA, Zlotin SG. Mendeleev Commun. 2010; 20: 140

• 84 Kayaki Y, Noguchi Y, Iwasa S, Ikariya T, Noyori R. Chem. Commun. (Cambridge) 1999; 1235

• 85 Li J, Jiang H, Chen M. Green Chem. 2001; 3: 137

• 86 Clifford AA, Pople K, Gaskill WJ, Bartle KD, Rayner CM. J. Chem. Soc., Faraday Trans. 1998; 94: 1451

• 87 Oakes RS, Heppenstall TJ, Shezad N, Clifford AA, Rayner CM. Chem. Commun. (Cambridge) 1999; 1459

• 88 Matsuo J.-i, Tsuchiya T, Odashima K, Kobayashi S. Chem. Lett. 2000; 178

• 89 Chapuis C, Kucharska A, Rzepecki P, Jurczak J. Helv. Chim. Acta 1998; 81: 2314

• 90 Fukuzawa S.-I, Metoki K, Komuro Y, Funazukuri T. Synlett 2002; 134

• 91 Fukuzawa S.-I, Matsuzawa H, Metoki K. Synlett 2001; 709

• 92 Weinstein RD, Renslo AR, Danheiser RL, Tester JW. J. Phys. Chem. B 1999; 103: 2878

• 93 Timko MT, Allen AJ, Danheiser RL, Steinfeld JI, Smith KA, Tester JW. Ind. Eng. Chem. Res. 2006; 45: 1594

• 94 Lee CKY, Holmes AB, Al-Duri B, Leeke GA, Santos RCD, Seville JPK. Chem. Commun. (Cambridge) 2004; 2622

• 95 Totoe H, McGowin AE, Turnbull K. J. Supercrit. Fluids 2000; 18: 131

• 96 Matsuda T, Harada T, Nakamura K, Ikariya T. Tetrahedron: Asymmetry 2005; 16: 909

• 97 Matsuda T, Harada T, Nakamura K. Curr. Org. Chem. 2005; 9: 299

• 98 Matsuda T, Harada T, Nakamura K. Green Chem. 2004; 6: 440

• 99 Matsuda T, Watanabe K, Harada T, Nakamura K. Catal. Today 2004; 96: 103

• 100 Željko K. J. Supercrit. Fluids 2009; 47: 357

• 101 Mesiano AJ, Beckman EJ, Russell AJ. Chem. Rev. 1999; 99: 623

• 102 Matsuda T, Kanamaru R, Watanabe K, Kamitanaka T, Harada T, Nakamura K. Tetrahedron: Asymmetry 2003; 14: 2087

• 103 Overmeyer A, Schrader-Lippelt S, Kasche V, Brunner G. Biotechnol. Lett. 1999; 21: 65

• 104 Hobbs HR, Kondor B, Stephenson P, Sheldon RA, Thomas NR, Poliakoff M. Green Chem. 2006; 8: 816

• 105 Mase N, Sako T, Horikawa Y, Takabe K. Tetrahedron Lett. 2003; 44: 5175

• 106 Albrycht M, Kiełbasiński P, Drabowicz J, Mikołajczyk M, Matsuda T, Harada T, Nakamura K. Tetrahedron: Asymmetry 2005; 16: 2015

• 107 Heo J.-H, Kim SY, Kim H.-S, Yoo K.-P. Biotechnol. Lett. 2000; 22: 995

• 108 Palocci C, Falconi M, Chronopoulou L, Cernia E. J. Supercrit. Fluids 2008; 45: 88

• 109 Salgın U, Salgın S, Takaç S. J. Supercrit. Fluids 2007; 43: 310

• 110 Celebi N, Yildiz N, Demir AS, Calimli A. J. Supercrit. Fluids 2007; 41: 386

• 111 Rantakyl M, Alkio M, Aaltonen O. Biotechnol. Lett. 1996; 18: 1089

• 112 Pasta P, Mazzola G, Carrea G, Riva S. Biotechnol. Lett. 1989; 11: 643

• 113 Mori T, Okahata Y. Chem. Commun. (Cambridge) 1998; 2215

• 114 Jeong N, Hwang SH, Lee YW, Lim JS. J. Am. Chem. Soc. 1997; 119: 10 549

• 115 Fürstner A, Ackermann L, Beck K, Hori H, Koch D, Langemann K, Liebl M, Six C, Leitner W. J. Am. Chem. Soc. 2001; 123: 9000

• 116 Rayner CM. Org. Process Res. Dev. 2007; 11: 121

• 117 Chateauneuf JE, Zhang J, Foote J, Brink J, Perkovic MW. Adv. Environ. Res. (Oxford, U. K.) 2002; 6: 487

• 118 Hrnjez BJ, Mehta AJ, Fox MA, Johnston KP. J. Am. Chem. Soc. 1989; 111: 2662

• 119 Andrew D, Des Islet BT, Margaritis A, Weedon AC. J. Am. Chem. Soc. 1995; 117: 6132

• 120 Nishiyama Y, Wada T, Kakiuchi K, Inoue Y. J. Org. Chem. 2012; 77: 5681

• 121 Nishiyama Y, Wada T, Asaoka S, Mori T, McCarty TA, Kraut ND, Bright FV, Inoue Y. J. Am. Chem. Soc. 2008; 130: 7526

• 122 Nishiyama Y, Wada T, Mori T, Inoue Y. Chem. Lett. 2007; 36: 1488

• 123 Nishiyama Y, Kaneda M, Asaoka S, Saito R, Mori T, Wada T, Inoue Y. J. Phys. Chem. A 2007; 111: 13 432

• 124 Nishiyama Y, Kaneda M, Saito R, Mori T, Wada T, Inoue Y. J. Am. Chem. Soc. 2004; 126: 6568

• 125 Ebert GW, Juda WL, Kosakowski RH, Ma B, Dong L, Cummings KE, Phelps MVB, Mostafa AE, Luo J. J. Org. Chem. 2005; 70: 4314

• 126 Ukai K, Aoki M, Takaya J, Iwasawa N. J. Am. Chem. Soc. 2006; 128: 8706

• 127 Ohishi T, Nishiura M, Hou Z. Angew. Chem. Int. Ed. 2008; 47: 5792

• 128 Takaya J, Tadami S, Ukai K, Iwasawa N. Org. Lett. 2008; 10: 2697

• 129 Ochiai H, Jang M, Hirano K, Yorimitsu H, Oshima K. Org. Lett. 2008; 10: 2681

• 130 Yeung CS, Dong VM. J. Am. Chem. Soc. 2008; 130: 7826

• 131 Metzger A, Bernhardt S, Manolikakes G, Knochel P. Angew. Chem. Int. Ed. 2010; 49: 4665

• 132 Boogaerts IIF, Nolan SP. J. Am. Chem. Soc. 2010; 132: 8858

• 133 Zhang L, Cheng J, Ohishi T, Hou Z. Angew. Chem. Int. Ed. 2010; 49: 8670

• 134 Boogaerts IIF, Fortman GC, Furst MRL, Cazin CSJ, Nolan SP. Angew. Chem. Int. Ed. 2010; 49: 8674

• 135 Vechorkin O, Hirt N, Hu X. Org. Lett. 2010; 12: 3567

• 136 Mizuno H, Takaya J, Iwasawa N. J. Am. Chem. Soc. 2011; 133: 1251

• 137 Takaya J, Iwasawa N. J. Am. Chem. Soc. 2008; 130: 15 254

• 138 Fujiwara S.-i, Asai A, Makita Y, Kambe N. J. Sulfur Chem. 2009; 30: 264

• 139 Babadzhanova LA, Kirij NV, Yagupolskii YL. J. Fluorine Chem. 2004; 125: 1095

• 140 Myers MC, Shah PP, Beavers MP, Napper AD, Diamond SL, Smith III AB, Huryn DM. Bioorg. Med. Chem. Lett. 2008; 18: 3646

• 141 Kondo K, Yokoyama S, Miyoshi N, Murai S, Sonoda N. Angew. Chem. Int. Ed. Engl. 1979; 18: 691

• 142 Zhao X, Yu Z, Zeng F, Chen J, Wu X, Wu S, Xiao W.-J, Zheng Z. Adv. Synth. Catal. 2005; 347: 877

• 143 Wu X, Yu Z. Tetrahedron Lett. 2010; 51: 1500

• 144 Lehr VS, Mattke T. US 2011 230 676, 2011 Chem. Abstr.. 2011 155 432 379

• 145 Mattke T, Böhling R, Knösche C, Lehr VS. US 2011 213 177, 2011 Chem. Abstr.. 2011 155 352 990

• 146 Krasil’nikov VV, Ignat’eva EV, Potoropin EB, Levchenko EV, Tagaev VI, Belousov EB. RU 2 372 326, 2009 Chem. Abstr.. 2009 151 528 459

• 147 Lorenz W, Boehm M, Adamson R, Steffens F, Hielscher A. US 2009 209 784, 2009 Chem. Abstr.. 2009 151 268 964

• 148 Stutz H, Halpaap R, Lewkebandara TS. EP 2 060 560, 2009 Chem. Abstr.. 2009 150 540 637

• 149 Stutz H, Diehl F, Schwarz A, Bruns R. US 2009 054 684, 2009 Chem. Abstr.. 2009 150 260 762

• 150 Keggenhoff B, Lokum H, Bohm M. US 2007 265 465, 2007 Chem. Abstr.. 2007 147 522 719

• 151 Smith RC, Carr RH. WO 2006 130 405, 2006 Chem. Abstr.. 2007 146 27 636

• 152 Sohn M, Stroefer E, Nevejans F, Penzel U, Pallasch H.-J, Leuthold R, Brodhagen A, Woelfert A, Mackenroth W, Maurer M. US 2006 252 960, 2006 Chem. Abstr.. 2006 145 471 164

• 153 Stuart JY. US 2006 041 166, 2006 Chem. Abstr.. 2006 144 233 590

• 154 Meyn J, Stutz H. US 2005 137 417, 2005 Chem. Abstr.. 2005 143 78 649

• 155 Kilgore UJ, Basuli F, Huffman JC, Mindiola DJ. Inorg. Chem. 2006; 45: 487

• 156 Su W, Zhong W, Bian G, Shi X, Zhang J. Org. Prep. Proced. Int. 2004; 36: 499

• 157 Charalambides YC, Moratti SC. Synth. Commun. 2007; 37: 1037

• 158 Davis MC, Dahl JEP, Carlson RMK. Synth. Commun. 2008; 38: 1153

• 159 Li H, Yang H, Petersen JL, Wang KK. J. Org. Chem. 2004; 69: 4500

• 160 Nagai A, Ochiai B, Endo T. Lett. Org. Chem. 2005; 2: 404

• 161 Ziessel R, Bonardi L, Retailleau P, Ulrich G. J. Org. Chem. 2006; 71: 3093

• 162 Bonardi L, Ulrich G, Ziessel R. Synlett 2006; 450

• 163 Oh LM, Spoors PG, Goodman RM. Tetrahedron Lett. 2004; 45: 4769

• 164 Vodička P, Streinz L, Vávra J, Koutek B, Buděšinský M, Ondráček J, Císařová I. Chirality 2005; 17: 378

• 165 Dyadyuchenko LV, Mikhailichenko SN, Dmitrieva IG, Zaplishny VN. Chem. Heterocycl. Compd. (Engl. Transl.) 2005; 41: 466

• 166 Lebedev AV, Lebedeva AB, Sheludyakov VD, Ovcharuk SN, Kovaleva EA, Ustinova OL. Russ. J. Gen. Chem. (Engl. Transl.) 2006; 76: 110

• 167 Lebedev AV, Lebedeva AB, Sheludyakov VD, Ovcharuk SN, Kovaleva EA, Ustinova OL. Russ. J. Gen. Chem. (Engl. Transl.) 2006; 76: 469

• 168 Lebedev AV, Lebedeva AB, Sheludyakov VD, Ovcharuk SN, Kovaleva EA, Ustinova OL. Russ. J. Gen. Chem. (Engl. Transl.) 2006; 76: 1069

• 169 Akhlaghinia B. Synthesis 2005; 1955

• 170 Akhlaghinia B, Samiei S. Phosphorus, Sulfur Silicon Relat. Elem. 2009; 184: 2525

• 171 Akhlaghinia B, Samiei S. Turk. J. Chem. 2007; 31: 35

• 172 Goryunov EI, Molchanova GN, Goryunova IB, Baulina TV, Petrovskii PV, Mikhailovskaya VS, Buyanovskaya AG, Nifant’ev EE. Russ. Chem. Bull. 2005; 54: 2626

• 173 Baulina TV, Petrovskii PV, Goryunov EI, Nifant’ev EE. Russ. J. Gen. Chem. (Engl. Transl.) 2010; 80: 1039

• 174 Le HV, Ganem B. Org. Lett. 2011; 13: 2584

• 175 Hojabri L, Kong X, Narine SS. Biomacromolecules 2009; 10: 884

• 176 ten Cate AT, Kooijman H, Spek AL, Sijbesma RP, Meijer EW. J. Am. Chem. Soc. 2004; 126: 3801

• 177 Patil BS, Vasanthakumar G.-R, Babu VVS. J. Org. Chem. 2003; 68: 7274

• 178 Sureshbabu VV, Venkataramanarao R, Hemantha HP. Int. J. Pept. Res. Ther. 2008; 34

• 179 Ichikawa Y. Synlett 2007; 2927

• 180 Sudarshan NS, Narendra N, Hemantha HP, Sureshbabu VV. J. Org. Chem. 2007; 72: 9804

• 181 Sureshbabu VV, Patil BS, Venkataramanarao R. J. Org. Chem. 2006; 71: 7697

• 182 Babu VVS, Kantharaju , Tantry SJ. Int. J. Pept. Res. Ther. 2005; 11: 131

• 183 Luzina EL, Popov AV. Eur. J. Med. Chem. 2009; 44: 4944

• 184 Ol’shevskaya VA, Zaitsev AV, Ayub R, Petrovskii PV, Kononova EG, Tatarskii Jr VV, Shtil AA, Kalinin VN. Dokl. Chem. (Engl. Transl.) 2005; 405: 230

• 185 Holt J, Andreassen T, Bakke JM, Fiksdahl A. J. Heterocycl. Chem. 2005; 42: 259

• 186 Reissig H.-U, Böttcher G, Zimmer R. Can. J. Chem. 2004; 82: 166

• 187 Yoshimura A, Luedtke MW, Zhdankin VV. J. Org. Chem. 2012; 77: 2087

• 188 Foltz C, Bellemin-Laponnaz S, Enders M, Wadepohl H, Gade LH. Org. Lett. 2008; 10: 305

• 189 Chaturvedi D, Ray S. J. Sulfur Chem. 2006; 27: 265

• 190 Singh SK, Singh KN. Phosphorus, Sulfur Silicon Relat. Elem. 2011; 186: 94

• 191 Chaturvedi D, Ray S. Monatsh. Chem. 2006; 137: 1219

• 192 Chaturvedi D, Ray S. Tetrahedron Lett. 2007; 48: 149

• 193 Maggi R, Malmassari C, Oro C, Pela R, Sartori G, Soldi L. Synthesis 2008; 53

• 194 Halimehjani AZ, Ebrahimi F, Azizi N, Saidi MR. J. Heterocycl. Chem. 2009; 46: 347

• 195 Aroua L, Baklouti A. Phosphorus, Sulfur Silicon Relat. Elem. 2007; 182: 2419

• 196 Uenishi K, Sudo A, Endo T. J. Polym. Sci., Part A: Polym. Chem. 2005; 43: 4422

• 197 Clegg W, Harrington RW, North M, Villuendas P. J. Org. Chem. 2010; 75: 6201

• 198 Movassagh B, Soleiman-Beigi M. Monatsh. Chem. 2008; 139: 927

• 199 Chaturvedi D, Chaturvedi AK, Mishra N, Mishra V. Tetrahedron Lett. 2008; 49: 4886

• 200 Aoyagi N, Ochiai B, Mori H, Endo T. Synlett 2006; 636

• 201 Chaturvedi D, Mishra N, Chaturvedi AK, Mishra V. Monatsh. Chem. 2008; 139: 1467

• 202 Movassagh B, Soleiman-Beigi M, Nazari M. Chem. Lett. 2008; 37: 22

• 203 Soleiman-Beigi M, Arzehgar Z, Movassagh B. Synthesis 2010; 392

• 204 Kiasat AR, Kazemi F, Savari A. Synth. Commun. 2008; 38: 1057

• 205 Téllez F, Cruz A, López-Sandoval H, Ramos-García I, Gayosso M, Castillo-Sierra RN, Paz-Michel B, Nöth H, Flores-Parra A, Contreras R. Eur. J. Org. Chem. 2004; 4203

• 206 Gaspari P, Banerjee T, Malachowski WP, Muller AJ, Prendergast GC, DuHadaway J, Bennett S, Donovan AM. J. Med. Chem. 2006; 49: 684

• 207 Azizi N, Aryanasab F, Saidi MR. Org. Lett. 2006; 8: 5275

• 208 Cao S.-L, Feng Y.-P, Jiang Y.-Y, Liu S.-Y, Ding G.-Y, Li R.-T. Bioorg. Med. Chem. Lett. 2005; 15: 1915

• 209 Hou X, Ge Z, Wang T, Guo W, Cui J, Cheng T, Lai C, Li R. Bioorg. Med. Chem. Lett. 2006; 16: 4214

• 210 Azizi N, Pourhasan B, Aryanasab F, Saidi MR. Synlett 2007; 1239

• 211 Gong Y.-D, Lee T. J. Comb. Chem. 2010; 12: 393

• 212 Gomez L, Gellibert F, Wagner A, Mioskowski C. J. Comb. Chem. 2000; 2: 75

• 213 Gomez L, Gellibert F, Wagner A, Mioskowski C. Tetrahedron Lett. 2008; 49: 2726

• 214 Wu J.-Y, Luo Z.-B, Dai L.-X, Hou X.-L. J. Org. Chem. 2008; 73: 9137

• 215 Greenbaum DC, Mackey Z, Hansell E, Doyle P, Gut J, Caffrey CR, Lehrman J, Rosenthal PJ, McKerrow JH, Chibale K. J. Med. Chem. 2004; 47: 3212

• 216 Lauria A, Bruno M, Diana P, Barraja P, Montalbano A, Cirrincione G, Dattolo G, Almerico AM. Bioorg. Med. Chem. 2005; 13: 1545

• 217 Koparır M, Cansız A, Demirdağ A. Molecules 2004; 9: 204

• 218 Padmavathi V, Thriveni P, Reddy BJM, Padmaja A. J. Heterocycl. Chem. 2005; 42: 113

• 219 Fox DL, Ruxer JT, Oliver JM, Alford KL, Salvatore RN. Tetrahedron Lett. 2004; 45: 401

• 220 Lu S.-F, Du D.-M, Xu J, Zhang S.-W. J. Am. Chem. Soc. 2006; 128: 7418

• 221 Döbele M, Wiehn MS, Bräse S. Angew. Chem. Int. Ed. 2011; 50: 11 533

• 222 Zakrzewski J, Krawczyk M. Phosphorus, Sulfur Silicon Relat. Elem. 2009; 184: 1880

• 223 Manjula SN, Malleshappa NN, Vipan PK, Manohara RSA, Ramani V, Gadad AK, Singh G, Gopalan KN, Mallikarjuna RC. Eur. J. Med. Chem. 2009; 44: 2923

• 224 Vermeulen M, Zwanenburg B, Chittenden GJF, Verhagen H. Eur. J. Med. Chem. 2003; 38: 729

• 225 Kremer C, Lützen A. Synthesis 2011; 210

• 226 Munch H, Hansen JS, Pittelkow M, Christensen JB, Boas U. Tetrahedron Lett. 2008; 49: 3117

• 227 Dabrowski R, Dziaduszek J, Garbat K, Filipowicz M, Urban S, Gauza S, Sasnouski G. Liq. Cryst. 2010; 37: 1529

• 228 Mays JR, Roska RLW, Sarfaraz S, Mukhtar H, Rajski SR. ChemBioChem 2008; 9: 729

• 229 Pedras MSC, Zheng Q.-A, Gadagi RS. Chem. Commun. (Cambridge) 2007; 368

• 230 Márquez JM, López Ó, Maya I, Fuentes J, Fernández-Bolaños JG. Tetrahedron Lett. 2008; 49: 3912

• 231 López Ó, Maya I, Fuentes J, Fernández-Bolaños JG. Tetrahedron 2004; 60: 61

• 232 Kaboudin B, Jafari E. Synthesis 2008; 2683

• 233 Chaskar AC, Bandgar BP, Modhave RK, Patil AB, Yewale S. Synth. Commun. 2009; 39: 992

• 234 Jamir L, Ali AR, Ghosh H, Chipem FAS, Patel BK. Org. Biomol. Chem. 2010; 8: 1674

• 235 Jamir L, Alimenla B, Kumar A, Sinha D, Sinha UB. Synth. Commun. 2011; 41: 147

• 236 Yella R, Kavala V, Patel BK. Synth. Commun. 2011; 41: 792

• 237 Ghosh H, Yella R, Ali AR, Sahoo SK, Patel BK. Tetrahedron Lett. 2009; 50: 2407

• 238 Ghosh H, Yella R, Nath J, Patel BK. Eur. J. Org. Chem. 2008; 6189

• 239 Bian G, Qiu H, Jiang J, Wu J, Lai G. Phosphorus, Sulfur Silicon Relat. Elem. 2007; 182: 503

• 240 Boas U, Gertz H, Christensen JB, Heegaard PMH. Tetrahedron Lett. 2004; 45: 269

• 241 Psurski M, Błażewska K, Gajda A, Gajda T, Wietrzyk J, Oleksyszyn J. Bioorg. Med. Chem. Lett. 2011; 21: 4572

• 242 Dubois J, Marchal A, Lacroix D, Cabou J. WO 2012 010 644, 2012 Chem. Abstr.. 2012 156 202 778

• 243 Chaskar AC, Yewale S, Bhagat R, Langi BP. Synth. Commun. 2008; 38: 1972

• 244 Bian G, Shan W, Su W. J. Chem. Res. 2005; 585

• 245 Wong R, Dolman SJ. J. Org. Chem. 2007; 72: 3969

• 246 Sureshbabu VV, Naik SA, Hemantha HP, Narendra N, Das U, Guru RTN. J. Org. Chem. 2009; 74: 5260

• 247 Sun N, Li B, Shao J, Mo W, Hu B, Shen Z, Hu X. Beilstein J. Org. Chem. 2012; 8: 61

• 248 Nath J, Jamir L, Patel BK. Green Chem. Lett. Rev. 2011; 4: 1

• 249 Nath J, Ghosh H, Yella R, Patel BK. Eur. J. Org. Chem. 2009; 1849

• 250 Mayekar SA, Chaskar AC, Mulwad VV. Synth. Commun. 2010; 40: 46

• 251 Yella R, Ghosh H, Murru S, Sahoo SK, Patel BK. Synth. Commun. 2010; 40: 2083

• 252 Huters AD, Quasdorf KW, Styduhar ED, Garg NK. J. Am. Chem. Soc. 2011; 133: 15 797

• 253 Richter JM, Ishihara Y, Masuda T, Whitefield BW, Llamas T, Pohjakallio A, Baran PS. J. Am. Chem. Soc. 2008; 130: 17 938

• 254 Chen X, Li Z, Sun X, Ma H, Chen X, Ren J, Hu K. Synthesis 2011; 3991

• 255 Demchenko AM, Yanchenko VA, Kisly VV, Lozinskii MS. Chem. Heterocycl. Compd. (Engl. Transl.) 2005; 41: 668

• 256 Menuel S, Porwanski S, Marsura A. New J. Chem. 2006; 30: 603

• 257 Ding M.-W, Fu B.-Q, Cheng L. Synthesis 2004; 1067

• 258 Vicente J, Abad J.-A, Lopez-Serrano J, Jones PG. Organometallics 2004; 23: 4711

• 259 Noshita T, Kidachi Y, Funayama H, Kiyota H, Yamaguchi H, Ryoyama K. Eur. J. Med. Chem. 2009; 44: 4931

• 260 Isoda T, Hayashi K, Tamai S, Kumagai T, Nagao Y. Chem. Pharm. Bull. 2006; 54: 1616

• 261 Tsotinis A, Afroudakis PA, Davidson K, Prashar A, Sugden D. J. Med. Chem. 2007; 50: 6436

• 262 Zhong B, Al-Awar RS, Shih C, Grimes JH, Vieth M, Hamdouchi C. Tetrahedron Lett. 2006; 47: 2161

• 263 Sotgiu G, Barbarella G. J. Org. Chem. 2007; 72: 4925

• 264 Aoyama T, Murata S, Arai I, Araki N, Takido T, Suzuki Y, Kodomari M. Tetrahedron 2006; 62: 3201

• 265 Gataullin RR, Fatykhov AA. Russ. J. Gen. Chem. (Engl. Transl.) 2008; 78: 442

• 266 Zhang S, Zhan T, Cheng K, Xia Y, Yang B. Eur. J. Med. Chem. 2008; 43: 2778

• 267 Zhang S.-S, Yang B, Li J.-Z, Li X.-M, Jie G.-F, Jiao K. Chin. J. Chem. 2005; 23: 543

• 268 Yadgire AV, Korpe GV, Deshmukh SP. E-J. Chem. 2011; 8: 1614

• 269 Iranpoor N, Firouzabadi H, Azadi R, Akhlaghinia B. J. Sulfur Chem. 2005; 26: 133

• 270 Iranpoor N, Firouzabadi H, Akhlaghinia B, Azadi R. Synthesis 2004; 92

• 271 Iranpoor N, Firouzabadi H, Nowrouzi N. Tetrahedron 2006; 62: 5498

• 272 Miyake H, Nakao Y, Sasaki M. Tetrahedron 2007; 63: 10 433

• 273 Azadi R, Mokhtari B, Makaremi M.-A. Chin. Chem. Lett. 2012; 23: 77

• 274 Mokhtari B, Azadi R, Rahmani-Nezhad S. Tetrahedron Lett. 2009; 50: 6588

• 275 Valette L, Poulain S, Fernandez X, Lizzani-Cuvelier L. J. Sulfur Chem. 2005; 26: 155

• 276 Arisawa M, Ashikawa M, Suwa A, Yamaguchi M. Tetrahedron Lett. 2005; 46: 1727

• 277 Kühne M, Györgydeák Z, Lindhorst TK. Synthesis 2006; 949

• 278 Koketsu M, Yamamura Y, Aoki H, Ishihara H. Phosphorus, Sulfur Silicon Relat. Elem. 2006; 181: 2699

• 279 Koketsu M, Yamamura Y, Ishihara H. Heterocycles 2006; 68: 1191

• 280 Zhou YD, Linden A, Heimgartner H. Helv. Chim. Acta 2011; 94: 1575

• 281 Atanassov PK, Linden A, Heimgartner H. Helv. Chim. Acta 2004; 87: 1452

• 282 Koketsu M, Otsuka T, Swenson D, Ishihara H. Org. Biomol. Chem. 2007; 5: 613

• 283 Koketsu M, Otsuka T, Ishihara H. Heterocycles 2006; 68: 2107

• 284 Hemantha HP, Sureshbabu VV. J. Pept. Sci. 2010; 16: 644

• 285 Chennakrishnareddy G, Nagendra G, Hemantha HP, Das U, Guru RTN, Sureshbabu VV. Tetrahedron 2010; 66: 6718

• 286 Møllendal H, Samdal S, Bunkan AJC, Guillemin J.-C. J. Phys. Chem. A 2012; 116: 4074

• 287 Banert K, Toth C. Angew. Chem. Int. Ed. Engl. 1995; 34: 1627

• 288 Barton DHR, Parekh SI, Tajbakhsh M, Theodorakis EA, Chi-Lam T. Tetrahedron 1994; 50: 639

• 289 Fernández-Bolaños JG, López Ó, Ulgar V, Maya I, Fuentes J. Tetrahedron Lett. 2004; 45: 4081

• 290 Su WK, Liang XR. J. Indian Chem. Soc. 2003; 80: 645

• 291 López Ó, Maza S, Ulgar V, Maya I, Fernández-Bolaños JG. Tetrahedron 2009; 65: 2556

• 292 Li H, Petersen JL, Wang KK. J. Org. Chem. 2003; 68: 5512

• 293 Amore A, van Heerbeek R, Zeep N, van Esch J, Reek JNH, Hiemstra H, van Maarseveen JH. J. Org. Chem. 2006; 71: 1851

• 294 Sandanayake S, Perera S, Ede NJ. QSAR Comb. Sci. 2004; 23: 655

• 295 Ali AR, Ghosh H, Patel BK. Tetrahedron Lett. 2010; 51: 1019

• 296 Chaudhari PS, Dangate PS, Akamanchi KG. Synlett 2010; 3065

• 297 Zhu C, Xu D, Wei Y. Synthesis 2011; 711

• 298 Jin C, Liu C, Su W. Synlett 2009; 607

• 299 Wu Y, Sun Q, Deng J, Tian W. J. Fluorine Chem. 2006; 127: 1152

• 300 Liang Y, He H.-W, Yang Z.-W. J. Heterocycl. Chem. 2011; 48: 88

• 301 Nie Y.-B, Wang L, Ding M.-W. J. Org. Chem. 2012; 77: 696

• 302 Zhao J.-F, Xie C, Xu S.-Z, Ding M.-W, Xiao W.-J. Org. Biomol. Chem. 2006; 4: 130

• 303 Zhao J.-F, Xie C, Ding M.-W, He H.-W. Chem. Lett. 2005; 34: 1022

• 304 Xu S.-Z, Cao M.-H, Ding M.-W, He H.-W. Chin. Chem. Lett. 2005; 16: 1177

• 305 Wang H.-Q, Liu Z.-J, Ding M.-W. Phosphorus, Sulfur Silicon Relat. Elem. 2004; 179: 2039

• 306 Ding M.-W, Huang N.-Y, He H.-W. Synthesis 2005; 1601

• 307 Xu S.-Z, Wu J, Cao M.-H, Ding M.-W. J. Heterocycl. Chem. 2010; 47: 68

• 308 Hu Y.-G, Wang Y, Du S.-M, Chen X.-B, Ding M.-W. Bioorg. Med. Chem. Lett. 2010; 20: 6188

• 309 Xie C, Huang N.-Y, Ding M.-W. ARKIVOC 2009; x, 220

• 310 Liu M.-G, Hu Y.-G, Ding M.-W. Tetrahedron 2008; 64: 9052

• 311 Li H.-X, Sun Y, Ding M.-W. Synth. Commun. 2008; 38: 4328

• 312 Rahman AKF, Nicholas KM. Tetrahedron Lett. 2007; 48: 6002

• 313 Anderson JC, Bou-Moreno R. Tetrahedron 2010; 66: 9182