A New Route to Pyrano[3,2-a]carbazole Ring Systems and Annulated Derivatives Thereof

Abstract

A new protocol based on sequential applications of Claisen rearrangement, olefin isomerisation, ring-closing diene/ enyne metathesis and Diels–Alder reaction has been developed to access pyrano[3,2-a]carbazole and annulated derivatives thereof.

Key words

heterocycles - metathesis - rearrangement - Diels–Alder reaction - isomerisation

• References

• 1a Chakraborty DP In Progress in the Chemistry of Organic Natural Products . Vol. 34. Herz W, Griesebach H, Kirby GW. Springer; Wien: 1977: 299-371
• 1b Knölker H.-J, Reddy KR. Chemistry and Biology of Carbazole Alkaloids . In The Alkaloids . Vol. 65. Cordell GA. Academic Press; Amsterdam: 2008: 1-430
• 1c Gruner KK, Knölker H.-J. Carbazoles and Acridines . In Heterocycles in Natural Product Synthesis . Majumdar KC, Chattopadhyay SK. Wiley-VCH; Weinheim: 2011: 341-364
• 2a Kirsch GH. Curr. Org. Chem. 2001; 5: 507
• 2b Knölker H.-J, Reddy KR. Chem. Rev. 2002; 102: 4303
• 2c Knölker H.-J. Top. Curr. Chem. 2005; 244: 115
• 2d Knölker H.-J. Chem. Lett. 2009; 38: 8
• 2e Knölker H.-J. Top. Curr. Chem. 2012; 309: 203
• 3a Wu T.-S, Huang S.-C, Wu P.-L. Heterocycles 1997; 45: 969
• 3b Bellina F, Rossi R. Tetrahedron 2006; 62: 7213
• 3c Bergman J, Janosik T, Wahlström N. Adv. Heterocycl. Chem. 2001; 80: 1
• 3d Prudhome M. Eur. J. Med. Chem. 2003; 38: 123
• 3e Pindur U, Kim Y.-S, Mehrabani F. Curr. Med. Chem. 1999; 6: 29
• 3f Fröhner W, Krahl MP, Reddy KR, Knölker H.-J. Heterocycles 2004; 63: 2393
• 3g Knölker H.-J. Curr. Org. Synth. 2004; 1: 309
• 4a Syam S, Abdul AB, Sukari MA, Mohan S, Abdelwahab SI, Wah TS. Molecules 2011; 16: 7155
• 4b Cui C.-B, Yan S.-Y, Cai B, Yao X.-S. J. Asian Nat. Prod. Res. 2002; 4: 233
• 4c Tachibana Y, Kikuzaki H, Lajis NH, Nakatani N. J. Agric. Food Chem. 2003; 51: 6461
• 5 Itoigawa M, Kashiwada Y, Ito C, Furukawa H, Tochibana Y, Bastow KF, Lee K.-H. J. Nat. Prod. 2000; 63: 893
• 6a Chakraborty DP, Islam A. J. Indian Chem. Soc. 1971; 48: 91
• 6b Knölker H.-J, Hofmann C. Tetrahedron Lett. 1996; 37: 7947
• 6c Lebold TP, Kerr MA. Org. Lett. 2007; 9: 1883
• 6d Gruner KK, Knölker H.-J. Org. Biomol. Chem. 2008; 6: 3902
• 6e Gruner KK, Hopfmann T, Matsumoto K, Jäger A, Katsuki T, Knölker H.-J. Org. Biomol. Chem. 2011; 9: 2057
• 6f Martin AE, Rajendra Prasad KJ. Collect. Czech. Chem. Commun. 2007; 72: 1579
• 6g Chattopadhyay SK, Ghosh D, Biswas T. Synlett 2006; 3358
• 6h Krishna Chaitanya T, Nagarajan R. Tetrahedron Lett. 2007; 48: 2489
• 7a Chattopadhyay SK, Maity S, Panja S. Tetrahedron Lett. 2002; 43: 7781
• 7b Chattopadhyay SK, Pal BK, Maity S. Chem. Lett. 2003; 32: 1190
• 7c Chattopadhyay SK, Dey R, Biswas S. Synthesis 2005; 403
• 8a Kotha S, Mandal K. Tetrahedron Lett. 2004; 45: 1391
• 8b Kotha S, Mandal K, Tiwari A, Mobin SM. Chem.–Eur. J. 2006; 12: 8024
• 8c Majumdar KC, Maji PK, Rahaman H, Roy B. Lett. Org. Chem. 2006; 3: 845
• 8d Pain C, Célanire S, Guillaumet G, Joseph B. Synlett 2003; 2089
• 8e Rotzoll S, Gorls H, Langer P. Synthesis 2008; 45

For reviews, see:
• 9a Castro AM. M. Chem. Rev. 2004; 104: 2939
• 9b Nubbemeyer U. Synthesis 2003; 961
• 9c Ziegler FE. Chem. Rev. 1988; 88: 1423
• 9d Blechert S. Synthesis 1989; 71
• 9e Bennett GB. Synthesis 1977; 589
• 10a Wakamatsu H, Nishida MN, Adachi N, Mori M. J. Org. Chem. 2000; 65: 3966
• 10b van Otterlo WA. L, Ngidi EL, de Koning CB. Tetrahedron Lett. 2003; 44: 6483
• 10c van Otterlo WA. L, Pathak R, de Koning CB. Synlett 2003; 1859
• 10d van Otterlo WA. L, Morgans GL, Khanye SD, Aderibigbe BA. A, Michael JP, Billing DG. Tetrahedron Lett. 2004; 45: 9171

For some recent reviews on isomerisation/RCM sequences, see:
• 11a van Otterlo WA. L, de Koning CB. Chem. Rev. 2009; 109: 3743
• 11b Schmidt B. Eur. J. Org. Chem. 2004; 1865
• 11c Dragutan V, Dragutan I. J. Organomet. Chem. 2006; 691: 5129
• 11d Donohoe TJ, O’Riordan TJ. C, Rosa CP. Angew. Chem. Int. Ed. 2009; 48: 1014

For some recent reports, see:
• 11e Mondal P, Thunder L, Chattopadhyay SK. Tetrahedron Lett. 2012; 53: 1328
• 11f Yadav DB, Morgans GL, Aderibigbe BA, Madeley LG, Fernandes MA, Michael JP, de Koning CB, van Otterlo WA. L. Tetrahedron 2011; 67: 2991
• 11g Kashaya Y, Hoshi K, Terada Y, Nishida A, Shuto S, Arisawa M. Eur. J. Org. Chem. 2009; 4606
• 11h Gross U, Nieger M, Brase S. Org. Lett. 2009; 11: 4740
• 11i Bennasar ML, Roca T, Monneris M, Garcia-Diaz D. J. Org. Chem. 2006; 71: 7028
• 12a Chattopadhyay SK, Biswas T, Neogi K. Chem. Lett. 2006; 35: 376
• 12b Chattopadhyay SK, Roy SP, Ghosh D, Biswas G. Tetrahedron Lett. 2006; 47: 6895
• 13a Kotha S, Mandal K, Tiwari A, Mobin SM. Chem.–Eur. J. 2006; 12: 8024
• 13b Majumdar KC, Rahaman H, Muhuri S, Roy B. Synlett 2006; 466
• 14a Li J, Lee D. Eur. J. Org. Chem. 2011; 4269
• 14b Monfette S, Fogg SD. Chem. Rev. 2009; 109: 3783
• 14c Herndon JW. Coord. Chem. Rev. 2009; 253: 86
• 14d Villar H, Frings M, Bolm C. Chem. Soc. Rev. 2007; 36: 55
• 14e Diver ST, Giessert AJ. Chem. Rev. 2004; 104: 1317
• 14f Diver ST. J. Mol. Catal. A: Chem. 2006; 254: 29
• 14g Kaliappan KP. Lett. Org. Chem. 2005; 678
• 14h Poulsen CS, Madsen R. Synthesis 2003; 1
• 14i Sémeril D, Bruneau C, Dixneuf PH. Adv. Synth. Catal. 2002; 344: 585
• 14j Mori M. Top. Organomet. Chem. 1999; 1: 133

For some earlier reports on RCM-mediated synthesis of dihydropyran derivatives, see:
• 14k Kobayashi T, Arisawa M, Shuto S. Org. Biomol. Chem. 2011; 9: 1219
• 14l Huang KS, Li SR, Wang YF. J. Chin. Chem. Soc. (Taipei) 2005; 52: 159
• 14m van Otterlo WA. L, Ngidi EL, Kuzvidza S, Morgans GL, Moleele SS, de Koning CB. Tetrahedron 2005; 61: 9996
• 14n Hardouin C, Burgaud L, Valleix A, Doris E. Tetrahedron Lett. 2003; 44: 435
• 14o Doodeman R, Rutjes FP. J. T, Hiemstra H. Tetrahedron Lett. 2000; 41: 5979
• 14p Harrity JP. A, La DS, Cefalo DR, Visser MS, Hoveyda AH. J. Am. Chem. Soc. 1998; 120: 2343
• 14q Harrity JP. A, Visser MS, Gleason JD. J. Am. Chem. Soc. 1997; 119: 1488
• 15 For a review on the synthesis of heterocycles using RCM and RCEYM, see: Chattopadhyay SK, Karmakar S, Biswas T, Majumdar KC, Rahman H, Roy B. Tetrahedron 2007; 63: 3919
• 16a Hansen EC, Lee D. Acc. Chem. Res. 2006; 39: 509
• 16b Boyer FD, Hanna I. Eur. J. Org. Chem. 2006; 471
• 16c Lloyd-Jones GC, Margue RG, Vries JG. Angew. Chem. Int. Ed. 2005; 44: 7442
• 16d Kitamura T, Sato Y, Mori M. Adv. Synth. Catal. 2002; 344
• 16e Fürstner A, Ackermann L, Gabor B, Goddard R, Lehmann CW, Mynott R, Stelzer F, Thiel OR. Chem.–Eur. J. 2001; 7: 3236
• 16f Randl S, Lucas N, Connon SJ, Blechert S. Adv. Synth. Catal. 2002; 344: 631
• 17 Lee H.-Y, Kim HY, Tae H, Kim BG, Lee J. Org. Lett. 2003; 5: 3439
• 18 We thank Professor S. T. Diver for some helpful discussions on the topic during a coffee break at the ISOM-2011 conference, Rennes, France

For some elegant but assorted reports, see:
• 19a Takahashi H, Yoshida K, Yanagisawa A. J. Org. Chem. 2009; 74: 3632
• 19b Ben-Othman R, Othman M, Coste S, Decroix B. Tetrahedron 2008; 64: 559
• 19c Virolleaud M, Piva O. Eur. J. Org. Chem. 2007; 1606
• 19d Kummer DA, Brenneman JB, Martin SF. Org. Lett. 2005; 7: 4621
• 19e Rosillo M, Dominguez G, Casarrubios L, Amador U, Pérez-Castells J. J. Org. Chem. 2004; 69: 2084
• 19f Imhof S, Blechert S. Synlett 2003; 609
• 19g Katritzky AR, Nair SK, Khokhlova T, Akhmedov NG. J. Org. Chem. 2003; 68: 5724
• 19h Saito N, Sato Y, Mori M. Org. Lett. 2002; 4: 803
• 19i Banti D, North M. Tetrahedron Lett. 2002; 43: 1561
• 19j Moreno-Mañas M, Pleixats R, Santamaria A. Synlett 2001; 1784
• 19k Duboc R, Henaut C, Savignac M, Genet JP, Bhatnagar N. Tetrahedron Lett. 2001; 42: 2461
• 19l Bentz D, Laschat S. Synthesis 2000; 1766
• 19m Lane C, Snieckus V. Synlett 2000; 1294
• 19n Schürer SC, Blechert S. Chem. Commun. 1999; 1203
• 19o Betkekar VV, Panda S, Kaliappan KP. Org. Lett. 2012; 14: 198
• 20 CCDC-747935 contains the crystal data for compound 20a. Triclinic; Space group P 1; unit cell parameters: a = 8.0008(3) Å, b = 11.2422(4) Å, c = 12.0749(5) Å. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif