γ-spiroiminolactone synthesis by reaction of acetylenic esters and α-dicarbonyl compounds in the presence of aryl isocyanide

Synthetic Communications

Volumn 35, Issue 21, 2005, Pages 2771-2777

  Maghsoodlou, Malek T ^a   Hazeri, Nourollah ^a   Habibi Khorasani, Sayyed M ^a   Marandi, Ghasem ^a   Nassiri, Mahmoud ^a  

^a UNIVERSITY OF SISTAN AND BALUCHESTAN   (Iran)

Author keywords

dicarbonyl compounds; Acetylenic esters; Iminolactones; Isocyanides; Three component reaction

Indexed keywords

1,2 DICARBONYL DERIVATIVE; ACETYLENE DERIVATIVE; ACETYLENIC ESTER; ARYL ISOCYANIDE; CYANIDE; GAMMA SPIROIMINOLACTONE; SPIRONOLACTONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; SYNTHESIS;

EID: 29144460225     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500290359     Document Type: Article

References (13)

1. Winterfeldt, E.; Schumann, D.; Dillinger, H. J. Additionen an die dreifachbindung XI struktur und reaktionen des 2:1-adduktes aus acetylenedicarbonester und isonitrilen. Chem. Ber 1969, 102, 1656-1664.
2. Oakes, T. R.; David, H. G.; Nagel, F. Small ring system from isocyanides. I. The reaction of isocyanides with hexaflurobutyne-2. J. Am. Chem. Soc 1969, 91 (17), 4761-4765.
3. Takisawa, T.; Obata, N.; Suzuki, Y.; Yanagida, T. A novel cycloaddition reaction of 4-bromo-2-dimethylphenylisonitrile with acetylene derivatives. Tetrahedron Lett. 1969, 10 (39), 3407-3410.
4. Ugi, I. Isonitrile Chemistry. In Organic Chemistry a Series of Monographes; Academic Press: New York, 1971; Vol. 20, pp. 3576-3600.
5. Ugi, I. From isocyanides via four-component condensations to antibiotic synthesis. Angew. Chem., Int. Ed. Engl. 1982, 21 (11), 810-819.
6. Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Strategies for via novel multicomponent reaction based on isocyanides and nucleophilic carbenes. Acc. Chem. Res 2003, 36, 899-907.
7. Yavari, I.; Maghsoodlou, M. T. Reaction between alkyl isocyanides and dimethyl acetylendicarboxylate in the presence of N,N′-dimethylbarbituric acid. A convenient route to highly functionalized 4-pyrano[3,2-d]pyrimidine derivatives. J. Chem. Res., Synop. 1998, 7, 386-387.
8. Nair, V.; Vinod, A. U.; Rajesh, C. A novel synthesis of 2-aninopyrroles using a three-component reaction. J. Org. Chem 2001, 66, 4427-4429.
9. Oakes, T. R.; Donovan, D. J. Reaction of isocyanides with activatied acetylenes in protic solvent. J. Org. Chem 1973, 38 (7), 1319-1325.
10. Dillinger, H. J.; Fengler, G.; Schumann, D.; Winterfeldt, E. Additionen an die dreifachbindung-XXII: Das thermodynamicsh kontrollierte adduct aus tert.butyl isonitril und acetylendicarbonester. Tetrahedron 1974, 30 (15), 2561-2564.
11. Nair, V.; Vinod, A. U. The reaction of cyclohexyl isocyanide and dimethyl acetylenedicarboxylate with aldehydes: A novel synthesis of 2-aminofuran derivatives. Chem. Comm. 2000, 12, 1019-1020.
12. Oliaruso, M. A.; Wolf, J. F. Synthesis of Lactones and Lactams; Wiley: New York, 1993.
13. Grieco, P. A. Methods for the synthesis of α-methylene lactones. Synthesis 1975, 2, 67-82.