Multicomponent reactions of pyridines, α-bromo carbonyl compounds and silylaryl triflates as aryne precursors: a facile one-pot synthesis of pyrido[2,1-a]isoindoles

Tetrahedron Letters

Volumn 50, Issue 2, 2009, Pages 208-211

  Huang, Xian ^a,b   Zhang, Tiexin ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aryne; Azomethine ylide; Multicomponent reaction; One pot synthesis; Pyrido 2,1 a isoindole

Indexed keywords

ACETIC ACID ETHYL ESTER; ALPHA BROMO ETHYLACETATE; ISOINDOLE DERIVATIVE; ISOQUINOLINE; KETONE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDO[2,1 A]ISOINDOLE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

EID: 56949091295     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.10.118     Document Type: Article

References (52)

1. Wang S., Cao L., Shi H., Dong Y., Sun J., and Hu Y. Chem. Pharm. Bull. 53 (2005) 67
2. Diana P., Martorana A., Barraja P., Montalbano A., Dattolo G., Cirrincione G., Dall' acque F., Salvador A., Vedaldi D., Basso G., and Viola G. J. Med. Chem. 51 (2008) 2387
3. Martínez-Viturroa C.M., and Domínguez D. Tetrahedron Lett. 48 (2007) 4707
4. Kabbe H.J. Justus Liebigs Ann. Chem. (1978) 398
5. Romanov N.N. Ukr. Khim. Zhur. (1981) 1280
6. Mitsumori T., Bendikov M., Dautel O., Wudl F., Shioya T., Sato H., and Sato Y. J. Am. Chem. Soc. 126 (2004) 16793
7. Augstein W., and Kröhnke F. Justus Liebigs Ann. Chem. (1966) 158
8. Hennige H., Kreher R., and Uhrig J. Synthesis (1982) 842
9. Fozard A., and Bradsher C.K. J. Org. Chem. 32 (1967) 2966
10. Bousquet T., Fleury J.-F., Daïch A., and Netchitaïlo P. Tetrahedron 62 (2006) 706
11. Bradsher C.K., and Voigt C.F. J. Org. Chem. 36 (1971) 1603
12. Fozard A., and Bradsher C.K. Tetrahedron Lett. 7 (1966) 3341
13. Matsumoto K., Uchida T., Sugi T., and Yagi Y. Chem. Lett. (1982) 869
14. Matsumoto K., Uchida T., Aoyama K., Nishikawa M., Kuroda T., and Okamoto T. J. Heterocycl. Chem. 25 (1988) 1798
15. Matsumoto K., Katsura H., Uchida T., Aoyama K., and Machiguchi T. J. Chem. Soc., Perkin Trans. 1 (1996) 2599
16. Dix I., Doll C., Hopf H., and Jones P.G. Eur. J. Org. Chem. 15 (2002) 2547
17. Mamane V., and Fort Y. Tetrahedron Lett. 47 (2006) 2337
18. Dömling A. Chem. Rev. 106 (2006) 17
19. Himeshima Y., Sonoda T., and Kobayashi H. Chem. Lett. (1983) 1211
20. Transition-metal induced MCRs of arynes:. Liu Z., and Larock R.C. Angew. Chem., Int. Ed. 46 (2007) 2535
21. Jeganmohan M., and Cheng C.-H. Org. Lett. 6 (2004) 2821
22. Jayanth T.T., Jeganmohan M., and Cheng C.-H. Org. Lett. 7 (2005) 2921
23. Nucleophilic addition MCRs of arynes:. Rigby J.H., and Laurent S. J. Org. Chem. 63 (1998) 6742
24. Yoshida H., Morishita T., Fukushima H., Ohshita J., and Kunai A. Org. Lett. 9 (2007) 3367
25. Huang X., and Xue J. J. Org. Chem. 72 (2007) 3965
26. Jeganmohan M., and Cheng C.-H. Chem. Commun. 23 (2006) 2454
27. Diels-Alder reaction of arynes:. Wang D.Z., Katz T.J., Golen J., and Rheingold A.L. J. Org. Chem. 69 (2004) 7769
28. Wood T.K., Piers W.E., Keay B.A., and Parvez M. Org. Lett. 8 (2006) 2875
29. [4+2] Cycloaddition of arynes:. Brecht R., Haenel F., Seitz G., Frenzen G., Pilz A., and Guénard D. Eur. J. Org. Chem. 11 (1998) 2451
30. Yoshida H., Watanabe M., Fukushima H., Ohshita J., and Kunai A. Org. Lett. 6 (2004) 4049
31. Gilmore C.D., Allan K.M., and Stoltz B.M. J. Am. Chem. Soc. 130 (2008) 1558
32. [2+2] Cycloaddition of arynes:. Okuma K., Okada A., Koga Y., and Yokomori Y. J. Am. Chem. Soc. 123 (2001) 7166
33. Aly A.A. Tetrahedron 59 (2003) 6067
34. Maurina P., Ibrahim-Ouali M., and Santelli M. Tetrahedron Lett. 42 (2001) 8147
35. [3 + 2] Cycloaddition of arynes. Liu Z., Shi F., Martinez P.D.G., Raminelli C., and Larock R.C. J. Org. Chem. 73 (2008) 219
36. Huang X.-C., Liu Y.-L., Liang Y., Pi S.-F., Wang F., and Li J.-H. Org. Lett. 10 (2008) 1525
37. Jin T., and Yamamoto Y. Angew. Chem., Int. Ed. 46 (2007) 3323
38. Raminelli C., Liu Z., and Larock R.C. J. Org. Chem. 71 (2006) 4689
39. Liu Z., Shi F., Martinez P.D.G., Raminelli C., and Larock R.C. J. Org. Chem. 73 (2008) 219
40. Huisgen R. Angew. Chem. 75 (1963) 604
41. Xue J., and Huang X. Synth. Commun. 38 (2007) 2179
42. Xue J., Yang Y.-W., and Huang X. Synlett (2007) 1533
43. Yoshida H., Fukushima H., Ohshita J., and Kunai A. Angew. Chem., Int. Ed. 43 (2004) 3935
44. Boekelheide V. Alkaloids (1960) 201
45. Hill R.K. Alkaloids (1967) 483
46. Reddy M.V.R., Rao M.R., Rhodes D., Hansen M.S.T., Rubins K., Bushman F.D., Venkateswarlu Y., and Faulkner D.J. J. Med. Chem. 42 (1999) 1901
47. Blank B., DiTullio N.W., Krog A.J., and Saunders H.L. J. Med. Chem. 21 (1978) 489
48. Shim Y.K., Youn J.I., Chun J.S., Park T.H., Kim M.H., and Kim W.J. Synthesis (1990) 753
49. Wormser H.C., and Abramson H.N. J. Heterocycl. Chem. 13 (1976) 113
50. Mumm O., and Dieberiechsen J. Justus. Liebigs Ann. Chem. (1939) 195
51. 3 (0.45 mmol) and CsF (1.2 mmol) were added rapidly. The reaction was carried out at 85 °C and monitored by TLC (7:1 P.E./EtOAc eluent). After total conversion of the triflate (about 0.8 h later), the reaction mixture was filtrated through a short pad of silica gel to remove indiscerptible materials, and then evaporated under vacuum to get rid of the solvent, and the residue was purified by chromatography (15:1 P.E./EtOAc eluent) to give 4a (about 49 mg) in 60% yield.
52. +: m/z 271.0997. Found 271.1004.