One-pot, three-component synthesis of highly functionalized pyrimidone derivatives and access to indole fused pyrimidones via palladium-catalyzed intramolecular Heck reaction

Tetrahedron

Volumn 70, Issue 23, 2014, Pages 3665-3674

  Lei, Ming ^a   Tian, Wan ^a   Li, Wei ^a   Lu, Ping ^a   Wang, Yanguang ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Indole fused pyrimidones; Intramolecular Heck reaction; Multi component reactions; Pyrimidone derivatives

Indexed keywords

1 (2 BROMO PHENYL) 2 [2 (4 METHOXY PHENYL) VINYL] 6 OXO 3 PHENYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (2 BROMO PHENYL) 2 [2 (4 NITRO PHENYL) VINYL] 6 OXO 3 PHENYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (2 BROMO PHENYL) 3 (4 METHOXY PHENYL) 2 [2 (4 METHOXY PHENYL) VINYL] 6 OXO 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (2 BROMO PHENYL) 3 (4 METHOXY PHENYL) 2 [2 (4 NITROPHENYL) VINYL] 6 OXO 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (2 BROMO PHENYL) 3 (4 METHOXY PHENYL) 6 OXO 2 STYRYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (2 BROMO PHENYL) 6 OXO 3 PHENYL 2 STYRYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (3 CHLORO PHENYL) 3 (4 METHOXY PHENYL) 6 OXO 2 STYRY 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (4 BROMO PHENYL) 2 [2 (4 METHOXY PHENYL) VINYL] 6 OXO 3 PHENYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (4 BROMO PHENYL) 2 [2 (4 NITRO PHENYL) VINYL] 6 OXO 3 PHENYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (4 BROMO PHENYL) 3 (4 METHOXY PHENYL) 2 [2 (4 METHOXYPHENYL) VINYL] 6 OXO 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (4 BROMO PHENYL) 3 (4 METHOXY PHENYL) 2 [2 (4 NITROPHENYL) VINYL] 6 OXO 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (4 BROMO PHENYL) 3 (4 METHOXY PHENYL) 6 OXO 2 STYRYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (4 BROMO PHENYL) 3 (4 METHOXY PHENYL) 6 OXO 2 STYRYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIETHYL ESTER; 1 (4 BROMO PHENYL) 3 (4 NITRO PHENYL) 6 OXO 2 STYRYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (4 BROMO PHENYL) 6 OXO 3 PHENYL 2 (2 PHENYL PROPENYL) 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (4 BROMO PHENYL) 6 OXO 3 PHENYL 2 STYRYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (4 FLUORO PHENYL) 3 (4 METHOXY PHENYL) 6 OXO 2 STYRYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (4 FLUORO PHENYL) 3 (4 METHOXY PHENYL) 6 OXO 2 STYRYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIETHYL ESTER; 1 (4 FLUORO PHENYL) 6 OXO 3 PHENYL 2 STYRYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1 (4 METHYL PHENYL) 6 OXO 3 PHENYL 2 STYRYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIMETHYL ESTER; 1,3 BIS (4 BROMO PHENYL) 6 OXO 2 STYRYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 1,3 BIS (4 METHOXY PHENYL) 6 OXO 2 STYRYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 3 (4 BROMO PHENYL) 1 (4 METHOXY PHENYL) 4 OXO 2 STYRYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID METHYL ESTER; 3 (4 METHOXY PHENYL) 1 (2 NITRO PHENYL) 6 OXO 2 STYRYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 3 (4 METHOXY PHENYL) 2 [2 (4 METHOXY PHENYL) VINYL] 6 OXO 1 P TOLYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 3 (4 METHOXY PHENYL) 6 OXO 1 PHENYL 2 STYRYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; 3 (4 METHOXY PHENYL) 6 OXO 2 STYRYL 1 P TOLYL 1,2,3,6 TETRAHYDRO PYRIMIDINE 4,5 DICARBOXYLIC ACID DIEMETHYL ESTER; ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; PYRIMIDINONE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CATALYST; CYCLOADDITION; DECARBOXYLATION; DRUG SOLUBILITY; HECK REACTION; HIGH TEMPERATURE; ISOMERIZATION; NUCLEOPHILICITY; ONE POT SYNTHESIS; PRIORITY JOURNAL; REACTION TIME; ROOM TEMPERATURE;

EID: 84899928039     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.04.023     Document Type: Article

References (38)

1. B. Ganem Acc. Chem. Res. 42 2009 463
2. A. Dömling, and I. Ugi Angew. Chem., Int. Ed. 39 2000 3169
3. V. Nair, C. Rajesh, A.U. Vinod, S. Bindu, A.R. Sreekanth, J.S. Mathen, and A.L. Balagopal Acc. Chem. Res. 36 2003 899
4. A. Dömling Chem. Rev. 106 2006 17
5. J.P. Zhu Eur. J. Org. Chem. 2003 1133
6. G.R. Madhavan, R. Chakrabarti, R.K. Vikramadithyan, R.N.V.S. Mamidi, V. Balraju, B.M. Rajesh, P. Misra, S.K.B. Kumar, B.B. Lohray, V.B. Lohray, and R. Rajagopalan Bioorg. Med. Chem. 10 2002 2671
7. I. Shcherbakova, G. Huang, O.J. Geoffroy, S.K. Nair, K. Swierczek, M.F. Balandrin, J. Fox, W.L. Heatona, and R.L. Conklina Bioorg. Med. Chem. Lett. 15 2005 2537
8. J.F. Wolfe, T.L. Rathman, M.C. Sleevi, J.A. Campell, and T.D. Greenwood J. Med. Chem. 33 1990 161
9. Y.F. Zhu, K. Wilcoxen, J. Saunders, Z. Guo, Y. Gao, P.J. Connors Jr., T.D. Gross, F.C. Tucci, R.S. Struthers, G.J. Reinhart, Q. Xie, and C. Chen Bioorg. Med. Chem. Lett. 12 2002 403
10. A. Salimbeni, R. Canevotti, F. Paleari, D. Poma, S. Caliari, F. Fici, R. Cirillo, A.R. Renzetti, A. Subissi, L. Belvisi, G. Bravi, C. Scolastico, and A. Giachetti J. Med. Chem. 38 1995 4806
11. W.F. Chiou, J.F. Liao, and C.F. Chen J. Nat. Prod. 59 1996 374
12. Y. Kobayashi, K. Hoshikuma, Y. Nakano, Y. Yokoo, and T. Kamiya Planta Med. 67 2001 244
13. V.M. Sharma, P. Prasanna, K.V.A. Seshu, B. Renuka, C.V.L. Rao, G.S. Kumar, C.P. Narasimhulu, P.A. Babu, R.C. Puranik, D. Subramanyam, A. Venkateswarlu, S. Rajagopal, K.B.S. Kumar, C.S. Rao, N.V.S. Mamidi, D.S. Deevi, R. Ajaykumar, and R. Rajagopalan Bioorg. Med. Chem. Lett. 12 2002 2303
14. Z.M. Xia, K. Wang, J.N. Zheng, Z.Y. Ma, Z.G. Jiang, X.X. Wang, and X. Lv Org. Biomol. Chem. 10 2012 1602
15. A.K. Bhattacharjee, D.J. Skanchy, B. Jennings, T.H. Hudson, J.J. Brendle, and K.A. Werbovetz Bioorg. Med. Chem. 10 2002 1979
16. C.W. Jao, W.C. Lin, Y.T. Wu, and P.L. Wu J. Nat. Prod. 71 2008 1275
17. M.H. Chen, L.S. Gan, S. Lin, X.L. Wang, L. Li, Y.H. Li, C.G. Zhu, Y.A. Wang, B.Y. Jiang, J.D. Jiang, Y.C. Yang, and J.G. Shi J. Nat. Prod. 75 2012 1167
18. Z.G. Zhang, C. Xue, X. Liu, Q. Zhang, and Q. Liu Tetrahedron 67 2011 7081
19. J.U. Jeong, X. Chen, A. Rahman, D.S. Yamashita, and J.I. Luengo Org. Lett. 6 2004 1013
20. A. Jezewski, J. Jurczak, Z. Lidert, and C.M. Tice J. Heterocycl. Chem. 38 2001 645
21. A. Sitte, and H. Paul Chem. Ber. 102 1969 615
22. E.C. Taylor, P. Zhou, and C.M. Tice Tetrahedron Lett. 38 1997 4343
23. M. Adib, H. Yavari, and M. Mollahosseini Tetrahedron Lett. 45 2004 1803
24. J.W. Ruan, and J.L. Xiao Acc. Chem. Res. 44 2011 614
25. A.B. Dounay, and L.E. Overman Chem. Rev. 103 2003 2945
26. N.J. Whitcombe, K.K. Hii, and S.E. Gibson Tetrahedron 57 2001 7449
27. L. Firmansjah, and G.C. Fu J. Am. Chem. Soc. 129 2007 11340
28. S.M. Ma, and B.K. Ni J. Org. Chem. 67 2002 8280
29. K.S. Bloome, R.L. McMahen, and E.J. Alexanian J. Am. Chem. Soc. 133 2011 20146
30. Q. Zang, S. Javed, P. Porubsky, F. Ullah, B. Neuenswander, G.H. Lushington, F.Z. Basha, M.G. Organ, and P.R. Hanson ACS Comb. Sci. 14 2012 211
31. L.-C. Campeau, M. Parisien, A. Jean, and K. Fagnou J. Am. Chem. Soc. 128 2006 581
32. P. Pinho, A.J. Minnaard, and B.L. Feringa Org. Lett. 5 2003 259
33. G. Abbiati, E.M. Beccalli, G. Broggini, and C. Zoni J. Org. Chem. 68 2003 7625
34. Y. Liu, B. Yao, C.L. Deng, R.Y. Tang, X.G. Zhang, and J.H. Li Org. Lett. 13 2011 1126
35. M. Lei, Z.J. Zhan, W. Tian, and P. Lu Tetrahedron 68 2012 3361
36. M. Lei, W. Tian, R.J. Hu, W. Li, and H. Zhang Synthesis 44 2012 2519
37. V. Nair, A.R. Sreekanth, N. Abhilash, M.M. Bhadbhade, and R.C. Gonnade Org. Lett. 4 2002 3575
38. H.S. Kim, H.S. Lee, S.H. Kim, and J.N. Kim Tetrahedron Lett. 50 2009 3154