Three-component one-pot synthesis of functionalized 1,2,3,6- tetrahydropyrano[4,3-6]pyrroles

Synthesis

Volumn , Issue 7, 2005, Pages 1049-1051

  Yavari, Issa ^a,b   Esnaashari, Manzarbanoo ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

2,6 dimethylphenyl isocyanide; Acetylenic esters; Methyl 2,4 dioxopentanoate; Three component reaction; Ugi reaction

Indexed keywords

CYANIDES; ORGANIC COMPOUNDS;

DIALKYL ACETYLENEDICARBOXYLATES; ISOCYANIDES;

SYNTHESIS (CHEMICAL);

1 (2,6 DIMETHYLPHENYL) 4 METHYL 2,3 DIOXO 1,2,3,6 TETRAHYDROPYRANO[4,3 B]PYRROLE 6,7 DICARBOXYLATE; 1,2,3,6 TETRAHYDROPYRANO[4,3 B]PYRROLE DERIVATIVE; 2,6 DIMETHYLPHENYL ISOCYANIDE; ACETYLENE DERIVATIVE; ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; CYANIDE; METHYL 2,4 DIOXOPENTANOATE; METHYL GROUP; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 18744378898     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-861839     Document Type: Article

References (17)

1. Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168.
2. Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathess, J. S.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899.
3. Marcaccini, S.; Torroba, T. Org. Prop. Proced. Int. 1993, 25, 141.
4. van Leusen, A. M. Synthesis 1991, 531.
5. van Leusen, A. M.; Siderius, H.; Hoogenboom, B. E.; van Leusen, D. Tetrahedron Lett. 1972, 13, 5337.
6. van Leusen, A. M.; Wildeman, J.; Oldenziel, O. H. J. Org. Chem. 1977, 42, 1153.
7. Schröder, R.; Schöllkopf, U.; Blume, E.; Hoppe, I. Liebigs Ann. Chem. 1975, 533.
8. Schöllkopf, U.; Porsch, P. H.; Blume, E. Liebigs Ann. Chem. 1976, 7122.
9. Yavari, I.; Djahaniani, H.; Nasiri, F. Synthesis 2004, 679.
10. Yavari, I.; Habibi, A. Synthesis 2004, 989.
11. Methyl 2,4-dioxopentanoate, which is apparently completely enolized in the liquid phase, was prepared based on the literature procedure for the ethyl ester: Marvel, C. S.; Dreger, E. E. Org. Synth. Coll. Vol. I 1941, 238.
12. a (λ = 0.7107 Å), T = 110 (2) K. The structure factors are available from the author upon request.
13. Levy, G. C.; Lichter, R. L. Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy; Wiley: New York, 1979.
14. Yavari, I.; Bayat, M. Tetrahedron 2003, 59, 2001.
15. Parker, K. A.; Midt, T. L. Org. Lett. 2001, 3, 3875.
16. Günther, H. NMR Spectroscopy, 2nd ed.; Wiley: New York, 1995, Chap. 9.
17. Anet, F. A. L.; Anet, R. In Dynamic Nuclear Magnetic Resonance Spectroscopy, Cotton, F. A.; Jackman, L. M., Eds.; Academic Press: New York, 1975, Chap. 8.