A sequential Pummerer-Diels-Alder route for the generation and trapping of furo[3,4-c]pyridines: Synthesis of heterocyclic analogues of 1-arylnaphthalene lignans

Journal of Organic Chemistry

Volumn 68, Issue 18, 2003, Pages 6919-6927

  Sarkar, Tarun K ^a   Panda, Niranjan ^a   Basak, Sankar ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

TRIGGERING AGENTS;

AROMATIZATION; CATALYSIS; DERIVATIVES; MOLECULAR STRUCTURE; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

ALKADIENE; ALKENYL GROUP; FURO[3,4 C]PYRIDINE DERIVATIVE; ISOQUINOLINE DERIVATIVE; LACTONE; LIGNAN; PYRIDINE DERIVATIVE; SULFONIC ACID DERIVATIVE; SULFOXIDE; TOLUENE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CYCLOADDITION; DIELS ALDER REACTION; HYDROXYLATION; RING OPENING;

CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS; INDICATORS AND REAGENTS; LIGNANS; MAGNETIC RESONANCE SPECTROSCOPY; NAPHTHALENES; PYRIDINES; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 0042338583     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0344081     Document Type: Article

References (35)

1. For reviews see: (a) Friedrichsen, W. Adv. Heterocycl. Chem. 1999, 73, 1.
2. (b) Traulsen, T.; Friedrichsen, W. Targets in Heterocyclic Systems: Chemistry and Properties; Societa Chimica Italiana: Roma, Italy, 1998; Vol. 2, p 59.
3. (c) Wege, D. Aust. J. Chem. 1998, 51, 1.
4. (d) Peters, O.; Friedrichsen, W. Trends Heterocycl. Chem. 1995, 4, 217.
5. (e) Friedrichsen, W. In Methoden der Organischen Chemie (Houben-Weyl); Kreher, R., Ed.; Thieme: New York, 1994; Vol. E6b1, pp 163.
6. (f) Rickborn, B. In Advances in Theoretically Interesting Molecules; Thummel, R. P., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1, pp 1-134.
7. (g) Rodrigo, R. Tetrahedron 1988, 44, 2093-2135.
8. (h) Wiersum, U. E. Aldrichim. Acta 1981, 14, 53.
9. (i) Friedrichsen, W. Adv. Heterocycl. Chem. 1980, 26, 135.
10. (j) Haddadin, M. J. Heterocycles 1978, 9, 865.
11. Padwa, A. Chem. Commun. 1998, 1417.
12. For a review on heteroisobenzofurans, see: Basak, S.; Ghosh S. K.; Sarkar T. K. J. Indian Inst. Sci. 2001, 81, 431-452.
13. (a) Sarkar, T. K.; Ghosh, S. K.; Nandy, S. K.; Chow, T. J. Tetrahedron Lett. 1999, 40, 397.
14. (b) Sarkar, T. K.; Ghosh S. K.; Chow, T. J. J. Org. Chem. 2000, 65, 3111.
15. (a) Sarkar, T. K.; Basak, S.; Ghosh S. K. Tetrahedron Lett. 2000, 41, 759.
16. (b) Sarkar, T. K.; Basak, S.; Slanina, Z.; Chow, T. J. J. Org. Chem. 2003, 68, 4206-4214.
17. Wiersum, U. E.; Eldred C. D.; Vrijhof, P.; Ven der Plas, H. C. Tetrahedron Lett. 1977, 1741-1742.
18. Iwao, M.; Inoue, H.; Kuraishi, T. Chem. Lett. 1984, 1263.
19. For generation of thieno[2,3-c]furans and furo[3,4-c]indoles via a Pummerer reaction: (a) Kappe, C. O.; Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 9285.
20. (b) Kappe, C. O.; Padwa, A. J. Org. Chem. 1996, 61, 6166.
21. Sarkar, T. K.; Basak, S.; Panda, N. Tetrahedron Lett. 2002, 43, 1341.
22. Bobbitt, J. M.; Scola, D. A. J. Org. Chem. 1960, 25, 560.
23. Compaigne, E.; Homfeld, E. J. Heterocycl. Chem. 1979, 16, 1321.
24. Professor H. K. Fun (Malaysia) kindly carried out the X-ray structure determination (unpublished results).
25. Usman, A.; Sarkar, T. K.; Panda, N.; Fun, H. K. Acta Crystallogr. 2002, E58, 1404.
26. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley-Interscience: New York, 1976.
27. The atomic coefficients were calculated with GAMESS.HF/3-21 G*. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, N.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347.
28. Nicolaou, K. C. Chem. Br. 1994, 30, 33.
29. Shepherd, T. A.; Jungheim, L. N.; Meyer, D. L.; Starling, J. J. Bioorg. Med. Chem. Lett. 1991, 1, 21.
30. Bailey, J. H.; Coulter, C. V.; Pratt, A. J.; Robinson, W. T. J. Chem. Soc., Perkin Trans. 1 1995, 589.
31. Fun, H. K.; Usman, A.; Razak, I. A.; Chantrapromma, S.; Sarkar, T. K.; Basak, S.; Panda, N. Acta Crystallogr. 2002, E58, 215.
32. (a) For a review on heterolignans, see: Ramos, A. C.; deClairac, R. P.-L.; Medarde, M. Heterocycles 1999, 51, 1443.
33. (b) Kuroda, T.; Takahashi, M.; Ogiku, T.; Ohmizu, H.; Nishitani, T.; Kondo, K.; Iwasaki, T. J. Org. Chem. 1994, 59, 7353.
34. Padwa, A.; Cochran, J. E.; Kappe, C. O. J. Org. Chem. 1996, 61, 3706.
35. Arnold, B. J.; Mellows, S.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1973, 1266.