Multicomponent reactions involving zwitterionic intermediates for the construction of heterocyclic systems: One pot synthesis of aminofurans and iminolactones

Tetrahedron

Volumn 59, Issue 51, 2003, Pages 10279-10286

  Nair, Vijay ^a   Vinod, A Unni ^a   Abhilash, N ^a   Menon, Rajeev S ^a   Santhi, V ^a   Varma, R Luxmi ^a   Viji, S ^a   Mathew, Saumini ^a   Srinivas, R ^b  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aldehydes; Dimethyl acetylenedicarboxylate; Isocyanides; Multicomponent reactions

Indexed keywords

ACETYLENE DERIVATIVE; ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; ALDEHYDE DERIVATIVE; AMPHOLYTE; CARBOXYLIC ACID DERIVATIVE; CYANIDE; CYCLOHEXYL ISOCYANIDE; DIMETHYL 2 (CYCLOHEXYLAMINO) 5 (3 NITROPHENYL) 3,4 FURANDICARBOXYLATE; DIMETHYL 2 (CYCLOHEXYLIMINO) 7 METHYL 8 OXO 1 SPIRO[4.5]DECA 3,6,9 TRIENE 3,4 DICARBOXYLATE; DIMETHYL 2 (CYCLOHEXYLIMINO) 8 OXO 1 SPIRO[4.5]DECA 3,6,9 TRIENE 3,4 DICARBOXYLATE; DIMETHYL 2 BENZOYL 5 (CYCLOHEXYLIMINO) 2 PHENYL 2,5 DIHYDRO 3,4 FURANDICARBOXYLATE; DIMETHYL 5 (CYCLOHEXYLIMINO) 2 METHYL 2 (4 NITROPHENYL) 2,5 DIHYDRO 3,4 FURANDICARBOXYLATE; DIMETHYL 6,7,9,10 TETRACHLORO 2 (CYCLOHEXYLIMINO) 8 OXO 1 SPIRO[4.5]DECA 3,6,9 TRIENE 3,4 DICARBOXYLATE; DIMETHYL 6,8 DI(TERT BUTYL) 2 (CYCLOHEXYLIMINO) 10 OXO 1 OXASPIRO[4.5]DECA 3,6,8 TRIENE 3,4 DICARBOXYLATE; DIMETHYL 6,8 DIBENZHYDRYL 2 (CYCLOHEXYLIMINO) 9 METHOXY 10 OXO 1 OXASPIRO[4.5]DECA 3,6,8 TRIENE 3,4 DICARBOXYLATE; DIMETHYL 7 (TERT BUTYL) 2 (CYCLOHEXYLIMINO) 10 OXO 1 OXASPIRO[4.5]DECA 3,6,8 TRIENE 3,4 DICARBOXYLATE; DIMETHYL 7,9 DI(TERT BUTYL) 2 (CYCLOHEXYLIMINO) 10 OXO 1 OXASPIRO[4.5]DECA 3,6,8 TRIENE 3,4 DICARBOXYLATE; DIMETHYL 7,9 DIBENZHYDRYL 2 (CYCLOHEXYLIMINO) 6 METHOXY 10 OXO 1 OXASPIRO[4.5]DECA 3,6,8 TRIENE 3,4 DICARBOXYLATE; DIMETHYL 8 (TERT BUTYL) 2 (CYCLOHEXYLIMINO) 10 OXO 1 OXASPIRO[4.5]DECA 3,6,8 TRIENE 3,4 DICARBOXYLATE; FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; LACTONE DERIVATIVE; QUINONE DERIVATIVE; SPIRO[1' METHYLINDOLE 1(2H) 4 CYCLOHEXYLIMINO 2,3 BIS(METHOXYCARBONYL)FURAN] 2 ONE; SPIRO[ACENAPHTHYLENE 1(2H) 4 CYCLOHEXYLIMINO 2,3 BIS(METHOXYCARBONYL)FURAN] 2 ONE; SPIRO[ANTHRACENE 1(2H) 4 CYCLOHEXYLIMINO 2,3 BIS(METHOXYCARBONYL)FURAN] 8 ONE; SPIRO[NAPHTHYLENE 1(2H) 4 CYCLOHEXYLIMINO 2,3 BIS(METHOXYCARBONYL)FURAN] 2 ONE; SPIRO[NAPHTHYLENE 1(2H) 4 CYCLOHEXYLIMINO 2,3 BIS(METHOXYCARBONYL)FURAN] 8 ONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; QUANTUM YIELD; STOICHIOMETRY; SYNTHESIS;

EID: 0345358011     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.10.052     Document Type: Article

References (40)

1. Winterfeldt E. Angew. Chem., Int. Ed. Engl. 6:1967;424.
2. (a) Johnson A.W., Tebby J.C. J. Chem. Soc. 1961;2126
3. (b) Tebby J.C., Wilson I.F., Griffiths D.V. J. Chem. Soc., Perkin Trans. 1. 1979;2133
4. (c) Butterfield P.J., Tebby J.C., Griffiths D.V. J. Chem. Soc., Perkin Trans. 1. 1979;1189
5. (d) Shaw M.A., Tebby J.C., Ward R.S., Williams D.H. J. Chem. Soc. (C). 1968;2795.
6. (a) Diels O., Alder K. Liebigs Ann. Chem. 16:1932;498
7. (b) Acheson R.M. Adv. Heterocycl. Chem. 1:1963;125
8. (c) Acheson R.M., Plunkett A.O. J. Chem. Soc. (London). 1964;2676.
9. (a) Winterfeldt E. Chem. Ber. 97:1964;1952
10. (b) Winterfeldt E., Dillinger H.J. Chem. Ber. 99:1966;1558.
11. Winterfeldt E. Chem. Ber. 98:1965;1518.
12. (a) Bestmann H.J., Rothe O. Angew. Chem. 76:1964;569
13. (b) Brown G.W., Cookson R.C., Stevens D.R. Tetrahedron Lett. 5:1964;1263.
14. Winterfeldt E., Schumann D., Dillinger H.J. Chem. Ber. 102:1969;1656.
15. (a) Nair V., Nair J.S., Vinod A.U., Rath N.P. J. Chem. Soc., Perkin Trans. 1. 1997;3129
16. (b) Nair V., Nair J.S., Vinod A.U. Synthesis. 2000;1713.
17. (a) Dillinger H.J., Fengler G., Schumann D., Winterfeldt E. Tetrahedron. 30:1974;2553
18. (b) Dillinger H.J., Fengler G., Schumann D., Winterfeldt E. Tetrahedron. 30:1974;2561
19. (c) Junjappa H., Saxena M.K., Ramaiah D., Loharay B.B., Rath N.P., George M.V. J. Org. Chem. 63:1998;9801
20. (d) Takizawa T., Obata N., Suzuki Y., Yanagida T. Tetrahedron Lett. 10:1969;3407
21. (e) Suzuki Y., Obata N., Takizawa T. Tetrahedron Lett. 11:1970;2667
22. (f) Oakes T.R., David H.G., Nagel F.J. J. Am. Chem. Soc. 91:1969;4761
23. (g) Oakes T.R., Donovan D.J. J. Org. Chem. 38:1973;1319
24. (h) Johnson F.A., Gulbenkian A.H., Naustavicus W. J. Chem. Soc., Chem. Commun. 1970;608
25. (i) Krebs A., Guntner A., Versteylen S., Schulz S. Tetrahedron Lett. 25:1984;2333.
26. Huisgen R. Angew. Chem., Int. Ed. Engl. 2:1963;565.
27. (a) Nair V., Sheela K.C., Radhakrishnan K.V., Rath N.P. Tetrahedron Lett. 39:1998;5627
28. (b) Nair V., Radhakrishnan K.V., Sheela K.C., Rath N.P. Tetrahedron. 55:1999;14199
29. (c) Nair V., Nair J.S., Vinod A.U., Rath N.P. J. Chem. Soc., Perkin Trans. 1. 1997;3129.
30. Weber L., Illgen K., Almstetter M. Synlett. 1999;366.
31. Dömling A., Ugi I. Angew. Chem., Int. Ed. Engl. 39:2000;3168.
32. Saegusa T., Taka-ishi N., Fujii H. Tetrahedron. 24:1968;3795.
33. Nair V., Vinod A.U. J. Chem. Soc., Chem. Commun. 2000;1019.
34. Nair V., Vinod A.U., Nair J.S., Sreekanth A.R., Rath N.P. Tetrahedron Lett. 41:2000;6675. The crystallographic data has been submitted to the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 220681.
35. Padwa A., Brodney M.A., Satake K., Straub C.S. J. Org. Chem. 64:1999;4617.
36. Lipschutz B.H. Chem. Rev. 86:1986;795.
37. (a) Roush W.R., Reily M.L., Koyama K., Brown B.B. J. Org. Chem. 62:1997;8708
38. (b) Roush W.R., Sciotti R. J. Am. Chem. Soc. 120:1998;7411
39. (c) Roush W.R., Sciotti R. J. Org. Chem. 63:1998;5473.
40. For preparation of cyclohexyl isocyanide see Ugi I., Meyr R., Lipinski M. Roberts J.D. Organic Syntheses. Vol. 41:1961;13 Wiley, New York.