FeCl3 catalysed two consecutive aminomethylation at the α-position of the β-dicarbonyl compounds: An easy access to hexahydropyrimidines and its spiro analogues

Tetrahedron Letters

Volumn 52, Issue 32, 2011, Pages 4153-4157

  Mukhopadhyay, Chhanda ^a   Rana, Sunil ^a   Butcher, Ray J ^b  

^a UNIVERSITY OF CALCUTTA   (India)

^b HOWARD UNIVERSITY   (United States)

Author keywords

Double aminomethylation; FeCl3; Hexahydropyrimidines; Lewis acid; Multicomponent reaction; Room temperature; Spiro compounds

Indexed keywords

1,3 DIARYL HEXAHYDROPYRIMIDINE; 2 (2,4 DIPHENYL 2,4 DIAZASPIRO 6 YL) INDANE 1,3 DIONE; 5 ACETYL 1,3 DIPHENYL HEXAHYDRO PYRIMIDINE 5 CARBOXYLIC ACID ETHYL ESTER; AMINE; BETA DICARBONYL; CARBONYL DERIVATIVE; DICHLOROMETHANE; ESTER DERIVATIVE; FERRIC CHLORIDE; FORMALDEHYDE; HEXAHYDROPYRIMIDINE; PYRIMIDINE DERIVATIVE; SPIRO COMPOUND; TETRAMETHYL 15 (4 METHYLPHENYL) 15 AZADISPIRO[5.1.5.3]HEXADECANE 1,5,9,13 TETRONE; UNCLASSIFIED DRUG;

AMINOMETHYLATION; ARTICLE; ATOM; CATALYSIS; COVALENT BOND; DRUG SYNTHESIS; METHYLATION; MULTICOMPONENT SYNTHESIS; ONE POT SYNTHESIS; ROOM TEMPERATURE; SYNTHESIS;

EID: 79960388530     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.05.144     Document Type: Article

References (32)

1. S. Groszkowki, L. Korzycka, and W. Bialasiewicz Pol. J. Parmacol. Pharm. 25 1973 573
2. Chem. Abstr. 1974, 80, 116181r.
3. L. Yi, and X. Xu Beijing Shifan Daxue Xuebao, Ziran Kexueban 2 1990 54
4. A.Q. Siddiqui, L. Merson-Davies, and P.M. Cullis J. Chem. Soc., Perkin Trans I 1999 3243
5. D. Hrvath J. Med. Chem. 40 1997 2412 and the references therein
6. R.J. Bergeron, and H.W. Seligsohn Bioorg. Chem. 14 1986 345
7. H. Finch, E.A. Peterson, and S.A. Ballard J. Am. Chem. Soc. 74 1952 2016
8. R.F. Evans Aust. J. Chem. 20 1967 1643
9. C. Jutz, A.F. Kirschner, and R.-M. Wagner Chem. Ber. 110 1977 1259
10. I.A. Perillo, M.B. Garcia, J.A. Bisceglia, and L.R. Orelli J. Heterocycl. Chem. 39 2002 655
11. A.R. Katrizky, S.K. Singh, and H.-Y. He J. Org. Chem. 67 2002 3115
12. M. Palko, M. Dervarics, and F. Fülöp ARKIVOC VI 2005 416
13. K. Chantrapromma, J.S. McManis, and B. Ganem Tetrahedron Lett. 21 1980 2475
14. K. Chantrapromma, and B. Ganem Tetrahedron Lett. 22 1981 23
15. S. Kambe, K. Saito, M. Hirose, A. Sakurai, and H. Midorikawa Synthesis 10 1984 860
16. Z.J. Beresnevicius, V. Mickevicius, K. Rutkauskas, and K. Kantminiene Polish J. Chem. Technol. 5 2003 75
17. H.-L. Wei, Z.-Y. Yan, Y.-N. Niu, G.-Q. Li, and Y.-M. Liang J. Org. Chem. 72 2007 8600
18. J. Zhu, and H. Bienayme Multicomponent Reactions 2005 WILEY-VCH GmbH & Co KGaA, Weinheim
19. A. Chanda, and V.V. Fokin Chem. Rev. 109 2009 725
20. D. Tejedor, and F. Garcia-Tellado Chem. Soc. Rev. 36 2007 484
21. C.C.A. Cariou, G.J. Clarkson, and M. Shipman J. Org. Chem. 73 2008 9762
22. S.M. Kupchan, Y. Komoda, W.A. Court, G.J. Thomas, R.M. Smith, A. Karim, C.J. Gilmore, R.C. Haltivanger, and R.F. Bryan J. Am. Chem. Soc. 94 1972 1354
23. R.W. Armstrong, A.P. Combs, P.A. Tempest, S.D. Brown, and T.A. Keating Acc. Chem. Res. 29 1996 123
24. L. Zhou, D.S. Bohle, H.F. Jiang, and C.J. Li Synlett 2009 937
25. G. Ren, J. Zhang, Z. Duan, M. Cui, and Y. Wu Aust. J. Chem. 62 2009 75
26. C. Mukhopadhyay, P.K. Tapaswi, and M.G.B. Drew Tetrahedron Lett. 51 2010 3944
27. N.G. Kozlov, and A.P. Kadutskii Tetrahedron Lett. 49 2008 4560
28. B.M. Trost Angew. Chem., Int. Ed. 34 1995 259
29. A.H. Blatt, and N. Gross J. Org. Chem. 29 1964 3306
30. S. Kobayashi, and H. Ishitani Chem. Rev. 99 1999 1069
31. C. Mannich, and W. Krosche Arch. Pharm. 250 1912 674
32. C. Mukhopadhyay, A. Datta, and R.J. Butcher Tetrahedron Lett. 50 2009 4246