Reaction between alkyl isocyanides and dimethyl acetylenedicarboxylate in the presence of polyhydroxybenzenes. Synthesis of 4H-chromene derivatives

Tetrahedron

Volumn 59, Issue 47, 2003, Pages 9409-9412

  Yavari, Issa ^a   Djahaniani, Hoorieh ^a   Nasiri, Farough ^a  

^a TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

4H chromene; Acetylenic ester; Alkyl isocyanides; OH acids

Indexed keywords

2,4 DIHYDROXYBENZALDEHYDE; 8 QUINOLINOL; ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; ALKYL GROUP; CATECHOL; CHROMENE DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; DIMETHYL 2 (CYCLOHEXYLAMINO) 5 HYDROXY 4H CHROMENE 3,4 DICARBOXYLATE; DIMETHYL 2 (CYCLOHEXYLAMINO) 6 FORMYL 5 HYDROXY 4H CHROMENE 3,4 DICARBOXYLATE; DIMETHYL 2 (CYCLOHEXYLAMINO) 6 HYDROXY 4H CHROMENE 3,4 DICARBOXYLATE; DIMETHYL 2 (CYCLOHEXYLAMINO) 6,7 HYDROXY 4H CHROMENE 3,4 DICARBOXYLATE; DIMETHYL 2 (TERT BUTYLAMINO) 4H PYRANO[3,2 H]QUINOLINE 3,4 DICARBOXYLATE; DIMETHYL 2 (TERT BUTYLAMINO) 6 FORMYL 5 HYDROXY 4H CHROMENE 3,4 DICARBOXYLATE; DIMETHYL 2 (TERT BUTYLAMINO) 8 HYDROXY 4H CHROMENE 3,4 DICARBOXYLATE; DIMETHYL 2 [(TERT BUTYLIMINO)METHYLENE] 3 (8 HYDROXY 7 QUINOLYL)SUCCINATE; HYDROQUINONE; ISOCYANIC ACID DERIVATIVE; PHENOL DERIVATIVE; PYROGALLOL; RESORCINOL; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0142153342     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.072     Document Type: Article

References (20)

1. Miao H., Yang Z. Org. Lett. 2:2000;1765.
2. Kumar P., Bodas M.S. Org. Lett. 2:2000;3821.
3. (a) Chauder B.A., Lopes C.C., Lopes R.S.C., Dasilva A.J.M., Snieckus V. Synthesis. 1998;279
4. (b) Schweizer E.E., Minami T., Crouse D.M.J. Org. Chem. 36:1971;4028.
5. Parker A.K., Mindt T.L. Org. Lett. 3:2001;3875.
6. Yu N., Aramini J.M., Germann M.W., Huang Z. Tetrahedron Lett. 41:2000;6993.
7. Hepworth J.D., Gabbutt C.D., Heron B.M. Katritzky A.R., Rees C.W., Scriven E.F.V. Comprehensive Heterocyclic Chemistry. Vol. 5:1996;351-468 Pergamon, Oxford.
8. Yavari I., Ramazani A. J. Chem. Res. (S). 1996;382.
9. Bloxam J., Dell C.P., Smith C.W. Heterocycles. 38:1994;399.
10. Elagamey A.G.A., Sawllim S.Z., El-Taweel F.M.A., Elnagdi M.H. Collect. Czech. Chem. Commun. 53:1988;1534.
11. (a) Yavari I., Adib M. Tetrahedron. 57:2001;5873.
12. (b) Yavari I., Adib M., Hojabri L. Tetrahedron. 57:2001;7537.
13. Yavari I., Adib M., Sayahi M.H. Tetrahedron Lett. 43:2002;2927.
14. Yavari I., Anary-Abbasinejad M., Alizadeh A. Tetrahedron Lett. 43:2002;4503.
15. Yavari I., Anary-Abbasinejad M., Alizadeh A., Hossaini Z. Tetrahedron. 59:2003;1289.
16. Ugi I. Isonitrile Chemistry. 1971;Academic, London.
17. Ugi I. Angew. Chem. Int. Ed. Engl. 21:1982;810.
18. Domling A., Ugi I. Angew. Chem. Int. Ed. Engl. 39:2000;3168.
19. Walborsky H.M., Periasamy M.P. Patai S., Rappoport Z. The Chemistry of Functional Groups. 1983;835 Wiley, New York. Chapter 20.
20. Marcaccini S., Torroba T. Org. Prep. Proced. 25:1993;141.