Pd-mediated synthesis of novel pentacyclic benzoazepino[2,1-a]isoindoles from enamides of Baylis-Hillman adducts

Tetrahedron Letters

Volumn 48, Issue 49, 2007, Pages 8619-8622

  Gowrisankar, Saravanan ^a   Lee, Hyun Seung ^a   Lee, Ka Young ^a   Lee, Ji Eun ^b   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

^b Gyeongsang National University   (South Korea)

Author keywords

Baylis Hillman adducts; Benzoazepino 2,1 a isoindole; Carbopalladation; Enamides

Indexed keywords

HYDROGEN; ISOINDOLE DERIVATIVE; PALLADIUM; PENTACYCLIC BENZOAZEPINO[2,1]ISOINDOLE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 35748950143     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.043     Document Type: Article

References (36)

1. Gowrisankar S., Kim S.J., Lee J.-E., and Kim J.N. Tetrahedron Lett. 48 (2007) 4419-4422
2. For the synthesis of medium-sized ring by palladium-mediated cyclization, see:. Alberico D., Scott M.E., and Lautens M. Chem. Rev. 107 (2007) 174-238
3. Dounay A.B., and Overman L.E. Chem. Rev. 103 (2003) 2945-2963
4. Qadir M., Cobb J., Sheldrake P.W., Whittall N., White A.J.P., Hii K.K., Horton P.N., and Hursthouse M.B. J. Org. Chem. 70 (2005) 1545-1551
5. Arnold L.A., Luo W., and Guy R.K. Org. Lett. 6 (2004) 3005-3007
6. Gibson S.E., Guillo N., and Tozer M.J. Chem. Commun. (1997) 637-638
7. Avila-Zarraga J.G., Lujan-Montelongo A., Covarrubias-Zuniga A., and Romero-Ortega M. Tetrahedron Lett. 47 (2006) 7987-7989
8. Soderberg B.C.G., Hubbard J.W., Rector S.R., and O'Neil S.N. Tetrahedron 61 (2005) 3637-3649
9. Ma S., and Negishi E.-i. J. Am. Chem. Soc. 117 (1995) 6345-6357
10. Tietze L.F., Sommer K.M., Schneider G., Tapolcsanyi P., Wolfling J., Muller P., Noltemeyer M., and Terlau H. Synlett (2003) 1494-1496
11. Ribiere P., Declerck V., Nedellec Y., Yadav-Bhatnagar N., Martinez J., and Lamaty F. Tetrahedron 62 (2006) 10456-10466
12. Declerck V., Ribiere P., Nedellec Y., Allouchi H., Martinez J., and Lamaty F. Eur. J. Org. Chem. (2007) 201-208
13. For the palladium-assisted cyclization involving enamide derivatives, see:. Kim G., Kim J.H., Kim W.-j., and Kim Y.A. Tetrahedron Lett. 44 (2003) 8207-8209
14. Grigg R., Loganathan V., Santhakumar V., Sridharan V., and Teasdale A. Tetrahedron Lett. 32 (1991) 687-690
15. For the examples of domino Heck-type double cyclization and related reactions, see:. Hulcoop D.G., and Lautens M. Org. Lett. 9 (2007) 1761-1764
16. Lee C.-W., Oh K.S., Kim K.S., and Ahn K.H. Org. Lett. 2 (2000) 1213-1216
17. Abdur Rahman S.M., Sonoda M., Itahashi K., and Tobe Y. Org. Lett. 5 (2003) 3411-3414
18. Couty S., Liegault B., Meyer C., and Cossy J. Org. Lett. 6 (2004) 2511-2514
19. Grigg R., Santhakumar V., Sridharan V., Stevenson P., Teasdale A., Thornton-Pett M., and Worakun T. Tetrahedron 47 (1991) 9703-9720
20. Zhang Y., Wu G.-z., Agnel G., and Negishi E.-i. J. Am. Chem. Soc. 112 (1990) 8590-8592
21. Carpenter N.E., Kucera D.J., and Overman L.E. J. Org. Chem. 54 (1989) 5846-5848
22. Wu G.-z., Lamaty F., and Negishi E.-i. J. Org. Chem. 54 (1989) 2507-2508
23. Poli G., and Giambastiani G. J. Org. Chem. 67 (2002) 9456-9459
24. 2 = 0.1154 (I > 2σ(I)). We omitted hydrogen atoms for clarity (Fig. 1). The X-ray data have been deposited in CCDC with number 655696.
25. 3: C, 76.12; H, 5.17; N, 4.23. Found: C, 76.22; H, 5.41; N, 4.21.
26. For the synthesis and biological activities of benzoazepino[2,1-a]isoindole moiety-containing compounds, see:. Lee Y.S., Min B.J., Park Y.K., Lee J.Y., Lee S.J., and Park H. Tetrahedron Lett. 40 (1999) 5569-5572
27. Pigeon P., and Decroix B. Tetrahedron Lett. 38 (1997) 1041-1042
28. Pigeon P., and Decroix B. Synth. Commun. 28 (1998) 2507-2516
29. Hilt G., Galbiati F., and Harms K. Synthesis (2006) 3575-3584
30. Walker G.N., Engle A.R., and Kempton R.J. J. Org. Chem. 37 (1972) 3755-3770
31. Heaney H., and Shuhaibar K.F. Tetrahedron Lett. 35 (1994) 2751-2752
32. Heaney H., and Shuhaibar K.F. Synlett (1995) 47-48
33. El Gihani M.T., Heaney H., and Shuhaibar K.F. Synlett (1996) 871-872
34. Ishihara Y., Tanaka T., Miwatashi S., Fujishima A., and Goto G. J. Chem. Soc., Perkin Trans. 1 (1994) 2993-2999
35. Gowrisankar S., Lee K.Y., and Kim J.N. Bull. Korean Chem. Soc. 26 (2005) 1112-1116
36. 1H NMR confirmed the presence of this compound: the three ABX protons at up-field region appeared, 2.03 (d, J = 10.5 Hz, 1H), 2.98 (dd, J = 10.5 and 4.2 Hz, 1H), 4.01 (d, J = 4.2 Hz, 1H).