Reaction of benzoyl chlorides with Huisgen's zwitterion: synthesis of functionalized 2,5-dihydro-1H-pyrroles and tetrasubstituted furans

Tetrahedron

Volumn 64, Issue 22, 2008, Pages 5221-5225

  Yavari, Issa ^a   Mokhtarporyani Sanandaj, Ako ^a   Moradi, Loghman ^a   Mirzaei, Anvar ^a  

^a TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

2,5 Dihydro 1H pyrrole; Aminofurans; Benzoyl chloride; Electron deficient acetylenes; Isocyanides

Indexed keywords

2,5 DIHYDRO 1H PYRROLE DERIVATIVE; AMPHOLYTE; BENZENECARBONYL CHLORIDE; BENZYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYANIDE; DI(TERT BUTYL) 1 CYCLOHEXYL 2 HYDROXY 5 OXO 2 PHENYL 2,5 DIHYDRO 1H PYRROLE 3,4 DICARBOXYLATE; DIALKYL ACETYLENEDICARBOXYLATE DERIVATIVE; DIETHYL 1 CYCLOHEXYL 2 HYDROXY 5 OXO 2 PHENYL 2,5 DIHYDRO 1H PYRROLE 3,4 DICARBOXYLATE; DIMETHYL 1 (2,6 DIMETHYLPHENYL) 2 HYDROXY 5 OXO 2 PHENYL 2,5 DIHYDRO 1H PYRROLE 3,4 DICARBOXYLATE; DIMETHYL 1 CYCLOHEXYL 2 HYDROXY 5 OXO 2 PHENYL 2,5 DIHYDRO 1H PYRROLE 3,4 DICARBOXYLATE; DIMETHYL 2 (1,1 DIMETHYLETHYL)AMINO 5 (4 NITROPHENYL) 3,4 FURANDICARBOXYLATE; DIMETHYL 2 (4 CHLOROPHENYL) 5 (CYCLOHEXYLAMINO) 3,4 FURANDICARBOXYLATE; DIMETHYL 2 (4 CHLOROPHENYL) 5 [(1,1,3,3 TETRAMETHYLBUTYL)AMINO] 3,4 FURANDICARBOXYLATE; DIMETHYL 2 (4 CHLOROPHENYL) 5 [(2,6 DIMETHYLPHENYL) AMINO] 2,4 FURANDICARBOXYLATE; DIMETHYL 2 (CYCLOHEXYLAMINO) 5 (4 NITROPHENYL) 3,4 FURANDICARBOXYLATE; FURAN DERIVATIVE; PYRROLE DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS; X RAY DIFFRACTION;

EID: 42749088760     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.03.044     Document Type: Article

References (18)

1. Winterfeldt E., Schumann D., and Dillinger H.J. Chem. Ber. 102 (1969) 1656
2. Dillinger H.J., Fengler G., Schumann D., and Winterfeldt E. Tetrahedron 30 (1974) 2553 and 2561
3. Junjappa H., Saxena M.K., Ramaiah D., Lohray B.B., Rath N.P., and George M.V. J. Org. Chem. 63 (1998) 9801
4. Nair V., Rajesh C., Vinod A.U., Bindu S., Sreekanth A.R., Mathen J.S., and Balagopal L. Acc. Chem. Res. 36 (2003) 899
5. Yavari I., Moradi L., Mokhtarporyani-Sanandaj A., and Mirzaei A. Helv. Chim. Acta 90 (2007) 392
6. Yavari I., and Moradi L. Helv. Chim. Acta 89 (2006) 1942
7. Yavari I., Moradi L., and Mirzaei A. Helv. Chim. Acta 89 (2006) 2918
8. Yavari I., and Moradi L. Tetrahedron Lett. 47 (2006) 1627
9. Yavari I., Mirzaei A., and Moradi L. Helv. Chim. Acta 89 (2006) 2825
10. Gilchrist T. J. Chem. Soc., Perkin Trans. 1 (2001) 2491
11. Donohoe T.J., Sintin H.O., Sisangia L., and Harling J.D. Angew. Chem., Int. Ed. 43 (2004) 2293
12. Corey E.J., and Li W.D.Z. Chem. Pharm. Bull. 47 (1999) 1
13. Bryans J.S., Large J.M., and Parsons A.F. J. Chem. Soc., Perkin Trans. 1 (1999) 2905
14. Mandal A.K., Hines J., Kuramoki K., and Crews C.M. Bioorg. Med. Chem. Lett. 15 (2005) 4043
15. Burnett A.M.N., and Johnson C.K. Oak Ridge National Laboratory Report ORNL-6895 (1996)
16. Domling A., and Ugi I. Angew. Chem., Int. Ed. 39 (2000) 3168
17. Domling A. Chem. Rev. 106 (2006) 17
18. Nair V., Vinod A.U., Abhilash N., Menon R.S., Santhi V., Varma R.L., Viji S., Mathew S., and Srinivas R. Tetrahedron 59 (2003) 10279