Synthesis 2012; 44(12): 1841-1848
DOI: 10.1055/s-0031-1289763
special topic
© Georg Thieme Verlag Stuttgart · New York

An Efficient Copper-Catalyzed Three-Component Synthesis of 3-C-Linked Glycosyl Iminocoumarins

Kalanidhi Palanichamy
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India, Fax: +91(22)25723480   Email: kpk@chem.iitb.ac.in
,
Sankar R. Suravarapu
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India, Fax: +91(22)25723480   Email: kpk@chem.iitb.ac.in
,
Krishna P. Kaliappan*
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India, Fax: +91(22)25723480   Email: kpk@chem.iitb.ac.in
› Author Affiliations
Further Information

Publication History

Received: 03 April 2012

Accepted: 10 April 2012

Publication Date:
10 May 2012 (online)

Abstract

An efficient general strategy was developed for the synthesis of previously unknown 3-C-linked glycosyl iminocoumarins. The strategy involves a copper-catalyzed multicomponent reaction of sugar-derived alkynes with tosyl azide and salicylaldehyde to give a diverse array of glycosyl iminocoumarins in good yields. These compounds can serve as appropriate precursors for the synthesis of the corresponding coumarin 3-C-glycosides.

Supporting Information

 
  • References


    • For general reviews on glycosides, see:
    • 1a Watanabe KA In The Chemistry of Nucleosides and Nucleotides . Townsend LB. Plenum Press; New York: 1994: 421
    • 1b Levy DE, Tang C. The Chemistry of C-Glycosides . Elsevier; Oxford: 1995
    • 1c Postema MH. D. C-Glycoside Synthesis . CRC Press; Boca Raton: 1995
    • 1d Shaban MA. E, Nasr AZ. Adv. Heterocycl. Chem. 1997; 68: 223
    • 1e Shaban MA. E. Adv. Heterocycl. Chem. 1997; 70: 163
    • 1f Beau JM, Gallagher T. Top. Curr. Chem. 1997; 187: 1
    • 1g Nicotra F. Top. Curr. Chem. 1997; 187: 55
    • 1h Krohn K, Rohr J. Top. Curr. Chem. 1997; 188: 127
    • 1i Du YG, Linhardt RJ, Vlahov IR. Tetrahedron 1998; 54: 9913
    • 1j Dondoni A, Marra A. Chem. Rev. 2000; 100: 4395
    • 1k Somsák L. Chem. Rev. 2001; 101: 81
    • 1l Liu L, McKee M, Postema MH. D. Curr. Org. Chem. 2001; 5: 1133
    • 1m Meo P, Osborn HM. I In Carbohydrates . Osborn HM. I. Academic Press; New York: 2003. Chap. 10 337
    • 1n Lee DY. W, He MS. Curr. Top. Med. Chem. 2005; 5: 1333
    • 1o Yuan X, Linhardt RJ. Curr. Top. Med. Chem. 2005; 5: 1393
    • 1p Lin C.-H, Lin H.-C, Yang W.-B. Curr. Top. Med. Chem. 2005; 5: 1431
    • 1q Adamo MF. A, Pergoli R. Curr. Org. Chem. 2008; 12: 1544
    • 1r Štambaský J, Hocek M, Kočovský P. Chem. Rev. 2009; 109: 6729
    • 2a Findlay JA, Lin J.-S, Radics L, Rachit S. Can. J. Chem. 1981; 59: 3018
    • 2b Sehgel SN, Czerkawski H, Kudelski A, Pander K, Saucier R, Vézina C. J. Antibiot. 1983; 36: 355
  • 3 Takahashi K, Yoshida M, Tomita F, Shirahata K. J. Antibiot. 1981; 34: 271
    • 4a Daves GD. Jr. Acc. Chem. Res. 1990; 23: 201
    • 4b Postema MH. D. Tetrahedron 1992; 48: 8545
    • 4c Togo H, He W, Waki Y, Yokoyama M. Synlett 1998; 700
    • 4d Isobe M, Nishizawa R, Hosokawa S, Nishikawa T. Chem. Commun. 1998; 2665
    • 4e Smoliakova IP. Curr. Org. Chem. 2000; 4: 589
    • 4f Taillefumier C, Chapleur Y. Chem. Rev. 2004; 104: 263
    • 4g Zou W. Curr. Top. Med. Chem. 2005; 5: 1363
    • 4h Saeeng R, Isobe M. Chem. Lett. 2006; 35: 552

    • For recent reviews on C-glycoside biology and biosynthesis, see:
    • 4i Compain P, Martin OR. Bioorg. Med. Chem. 2001; 9: 3077
    • 4j Hultin PG. Curr. Top. Med. Chem. 2005; 5: 1299
    • 4k Bililign T, Griffith BR, Thorson JS. Nat. Prod. Rep. 2005; 22: 742
    • 4l Wellington KW, Benner SA. Nucleosides, Nucleotides Nucleic Acids 2006; 25: 1309

      For selected reviews and papers on coumarin derivatives and their biological applications, see:
    • 5a Murray RD. H, Mendez J, Brown SA. The Natural Coumarins: Occurrence, Chemistry, and Biochemistry . Wiley; Chichester: 1982
    • 5b Murray RD. H. Nat. Prod. Rep. 1995; 12: 477
    • 5c O’Kennedy R, Thornes RD. Coumarins: Biology, Applications and Mode of Action . Wiley; Chichester: 1997
    • 5d Sardari S, Nishibe S, Daneshtalab M. Stud. Nat. Prod. Chem. 2000; 23: 335
    • 5e Murray RD. H. Prog. Chem. Org. Nat. Prod. 2002; 83: 1
    • 5f Garazd MM, Garazd YL, Khilya VP. Chem. Nat. Compd. 2003; 39: 54
    • 5g Chinchilla R, Nájera C, Yus M. Chem. Rev. 2004; 104: 2667
    • 5h Zhao Y, Zheng Q, Dakin K, Xu K, Martinez ML, Li W.-H. J. Am. Chem. Soc. 2004; 126: 4653
    • 5i Kuo P.-Y, Yang D.-Y. J. Org. Chem. 2008; 73: 6455
  • 6 Dubois M.-A, Wierer M, Wagner H. Phytochemistry 1990; 29: 3369
  • 7 Garazd YL, Kornienko EM, Maloshtan LN, Garazd MM, Khilya VP. Chem. Nat. Compd. 2005; 5: 508
  • 8 Burlison JA, Avila C, Vielhauer G, Lubbers DJ, Holzbeierlein J, Blagg BS. J. J. Org. Chem. 2008; 73: 2130
    • 9a Musicki B, Periers A.-M, Piombo L, Laurin P, Klich M, Dupuis-Hamelin C, Lassaigne P, Bonnefoy A. Tetrahedron Lett. 2003; 44: 9259
    • 9b Scatigno AC, Garrido SS, Marchetto R. J. Pept. Sci. 2004; 10: 566
    • 10a Coleman RS, Madaras ML. J. Org. Chem. 1998; 63: 5700
    • 10b Coleman RS, Berg MA, Murphy CJ. Tetrahedron 2007; 63: 3450

      For selected examples, see:
    • 11a Sarker SD, Waterman PG. J. Nat. Prod. 1995; 58: 1109
    • 11b Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893
    • 11c Borges F, Roleira F, Milhazes N, Santana L, Uriarte E. Curr. Med. Chem. 2005; 12: 887
    • 11d Ngameni B, Touaibia M, Patnam R, Belkaid A, Sonna P, Ngadjui BT, Anabi B, Roy R. Phytochemistry 2006; 67: 2573
    • 11e Su J, Wu Z.-J, Zhang W.-D, Zhang C, Li H.-L, Liu R.-H, Shen Y.-H. Chem. Pharm. Bull. 2008; 56: 589
    • 11f Akak CM, Djama CM, Nkengfack AE, Tu P.-F, Lei L.-D. Fitoterapia 2010; 81: 873
  • 12 Batsurén D, Batirov ÉKh, Malikov VM, Yagudaev MR. Khim. Prir. Soedin. 1983; 142 ; Chem. Nat. Compd. 1983, 19, 134
    • 13a Batsurén D, Batirov ÉKh, Malikov VM. Khim. Prir. Soedin. 1982; 650 ; Chem. Nat. Compd. 1983, 18, 616
    • 13b Vdovin AD, Batsurén D, Batirov ÉKh, Yagudaev MR, Malikov VM. Khim. Prir. Soedin. 1983; 441 ; Chem. Nat. Compd. 1984, 19, 413
    • 13c Aminov SD, Vakhabov AA. Dokl. Akad. Nauk SSSR 1985; 44
  • 14 Hirakura K, Saida I, Fukai T, Nomura T. Heterocycles 1985; 23: 2239
    • 15a O’Callaghan CN, Conalty ML. Proc. R. Ir. Acad., Sect. B 1979; 6: 87
    • 15b Burke TR. Jr, Lim B, Marquez VE, Li Z.-H, Bolen JB, Stefanova I, Horak ID. J. Med. Chem. 1993; 36: 425
  • 16 Mahling J.-A, Schmidt RR. Liebigs Ann. 1995; 467
    • 17a Toshima K, Matsuo G, Ishizuka T, Ushiki Y, Nakata M, Matsumura S. J. Org. Chem. 1998; 63: 2307
    • 17b Telbani EE, Desoky SE, Hammad MA, Rahman AR. H. A, Schmidt RR. Eur. J. Org. Chem. 1998; 2317
    • 17c Oyama K, Kondo T. J. Org. Chem. 2004; 69: 5240
    • 17d See also ref. 4k
  • 18 Saha NN, Desai VN, Dhavale DD. J. Org. Chem. 1999; 64: 1715
    • 19a Giguère D, Patnam R, Juarez-Ruiz JM, Neault M, Roy R. Tetrahedron Lett. 2009; 50: 4254
    • 19b Giguère D, Cloutier P, Roy R. J. Org. Chem. 2009; 74: 8480

      For selected papers and reviews on multicomponent reactions, see:
    • 20a Bienaymé H, Hulme C, Oddon G, Schmitt P. Chem.–Eur. J. 2000; 6: 3321
    • 20b Dömling A, Ugi I. Angew. Chem. Int. Ed. 2000; 39: 3168
    • 20c Zhu J. Eur. J. Org. Chem. 2003; 1133
    • 20d Marcaccini S, Miguel D, Torroba T, García-Valverde M. J. Org. Chem. 2003; 68: 3315
    • 20e Nair V, Rajesh C, Vinod AU, Bindu S, Sreekanth AR, Mathen JS, Balagopal L. Acc. Chem. Res. 2003; 36: 899
    • 20f Appukkuttan P, Dehaen W, Fokin VV, Van der Eycken E. Org. Lett. 2004; 6: 4223
    • 20g Byk G, Kabahn E. J. Comb. Chem. 2004; 6: 596
    • 20h Liéby-Muller F, Constantieux T, Rodriguez J. J. Am. Chem. Soc. 2005; 127: 17176
    • 20i Ramon DJ, Yus M. Angew. Chem. Int. Ed. 2005; 44: 1602
    • 20j Multicomponent Reactions . Zhu J, Bienaymé H. Wiley-VCH; Weinheim: 2005
    • 20k Dömling A. Chem. Rev. 2006; 106: 17
    • 21a Bae I, Han H, Chang S. J. Am. Chem. Soc. 2005; 127: 2038
    • 21b Cho SH, Yoo EJ, Bae I, Chang S. J. Am. Chem. Soc. 2005; 127: 16046
    • 21c Yoo EJ, Bae I, Cho SH, Han H, Chang S. Org. Lett. 2006; 8: 1347

      For recent reviews, see:
    • 22a Yoo EJ, Chang S. Curr. Org. Chem. 2009; 13: 1766
    • 22b Lu P, Wang Y.-G. Synlett 2010; 165
    • 22c Kim SH, Park SH, Choi JH, Chang S. Chem.–Asian J. 2011; 6: 2618
    • 23a Chang S, Lee M, Jung DY, Yoo EJ, Cho SH, Han SK. J. Am. Chem. Soc. 2006; 128: 12366
    • 23b Yoo EJ, Ahlquist M, Kim SH, Bae I, Fokin VV, Sharpless KB, Chang S. Angew. Chem. Int. Ed. 2007; 46: 1730
    • 23c Cho SH, Chang S. Angew. Chem. Int. Ed. 2007; 46: 1897
    • 23d Cho SH, Chang S. Angew. Chem. Int. Ed. 2008; 47: 2836
    • 23e Yoo EJ, Ahlquist M, Bae I, Sharpless KB, Fokin VV, Chang S. J. Org. Chem. 2008; 73: 5520
    • 23f Kim J, Lee SY, Lee J, Do Y, Chang S. J. Org. Chem. 2008; 73: 9454
    • 23g Yoo EJ, Chang S. Org. Lett. 2008; 10: 1163
    • 23h Hwang SJ, Cho SH, Chang S. Pure Appl. Chem. 2008; 80: 873
    • 23i Kim JY, Kim SH, Chang S. Tetrahedron Lett. 2008; 49: 1745
    • 23j Yoo EJ, Park SH, Lee SH, Chang S. Org. Lett. 2009; 11: 1155
    • 23k Lee MY, Kim MH, Kim J, Kim SH, Kim BT, Jeong IH, Chang S, Kim SH, Chang S.-Y. Bioorg. Med. Chem. Lett. 2010; 20: 541
    • 23l Husmann R, Na YS, Bolm C, Chang S. Chem. Commun. 2010; 46: 5494
    • 24a Cui S.-L, Lin X.-F, Wang Y.-G. Org. Lett. 2006; 8: 4517
    • 24b Cui S.-L, Wang J, Wang Y.-G. Org. Lett. 2007; 9: 5023
    • 24c Cui S.-L, Wang J, Wang Y.-G. Org. Lett. 2008; 10: 13
    • 24d Cui S.-L, Wang J, Wang Y.-G. Org. Lett. 2008; 10: 1267
    • 24e Cui S.-L, Wang J, Wang Y.-G. Tetrahedron 2008; 64: 487
    • 24f Lu W, Song W, Hong D, Lu P, Wang Y.-G. Adv. Synth. Catal. 2009; 351: 1768
    • 24g She J, Jiang Z, Wang Y.-G. Synlett 2009; 2023
    • 24h Jin H, Xu X, Gao J, Zhong J, Wang Y.-G. Adv. Synth. Catal. 2010; 352: 347
    • 24i Shen Y, Cui S, Wang J, Chen X, Lu P, Wang Y.-G. Adv. Synth. Catal. 2010; 352: 1139
    • 24j Song W, Lei M, Shen Y, Cai S, Lu W, Lu P, Wang Y.-G. Adv. Synth. Catal. 2010; 352: 2432
    • 24k Song W, Lu W, Wang J, Lu P, Wang Y.-G. J. Org. Chem. 2010; 75: 3481
    • 24l Wang J, Wang J, Zhu Y, Lu P, Wang Y.-G. Chem Commun. 2011; 47: 3275
    • 24m Li Y, Hong D, Zhu Y, Lu P, Wang Y.-G. Tetrahedron 2011; 67: 8086
    • 25a Cassidy MP, Raushel J, Fokin VV. Angew. Chem. Int. Ed. 2006; 45: 3154
    • 25b Whiting M, Fokin VV. Angew. Chem. Int. Ed. 2006; 45: 3157
    • 25c Mandal S, Gauniyal HM, Pramanik K, Mukhopadhyay B. J. Org. Chem. 2007; 72: 9753
    • 25d Xu X, Cheng D, Li J, Guo H, Yan J. Org. Lett. 2007; 9: 1585
    • 25e Wang F, Fu H, Jiang Y, Zhao Y. Adv. Synth. Catal. 2008; 350: 1830
    • 25f Shang Y, He X, Hu J, Wu J, Zhang M, Yu S, Zhang Q. Adv. Synth. Catal. 2009; 351: 2709
    • 25g Yao W, Pan L, Zhang Y, Wang G, Wang X, Ma C. Angew. Chem. Int. Ed. 2010; 49: 9210
    • 25h Shang Y, Ju K, He X, Hu J, Yu S, Zhang M, Liao K, Wang L, Zhang P. J. Org. Chem. 2010; 75: 5743
    • 25i Chen Z, Ye C, Gao L, Wu J. Chem. Commun. 2011; 47: 5623
    • 25j Chen Z, Zheng D, Wu J. Org. Lett. 2011; 13: 848
    • 25k Li S, Luo Y, Wu J. Org. Lett. 2011; 13: 3190
    • 25l Li S, Luo Y, Wu J. Org. Lett. 2011; 13: 4312
    • 25m Namitharan K, Pitchumani K. Org. Lett. 2011; 13: 5728
    • 25n Liu Y, Wang X, Xu J, Zhang Q, Zhao Y, Hu Y. Tetrahedron 2011; 67: 6294
    • 26a Kaliappan KP, Subrahmanyam AV. Org. Lett. 2007; 9: 1121
    • 26b Kaliappan KP, Kalanidhi P, Mahapatra S. Synlett 2009; 2162
    • 26c Subrahmanyam AV, Palanichamy K, Kaliappan KP. Chem.–Eur. J. 2010; 16: 8545
    • 26d Khangarot RK, Kaliappan KP. Eur. J. Org. Chem. 2011; 6117
    • 27a Betkekar VV, Panda S, Kaliappan KP. Org. Lett. 2012; 14: 198
    • 27b Alkyne 10 was synthesized by methylation of the corresponding propargylic tertiary alcohol, see: Ramana CV, Mallik R, Gonnade RG. Tetrahedron 2008; 64: 219