Intermolecular Dipolar Cycloaddition Reactions of 5H,7H-Thiazolo[3,4-c]oxazol-4...

• Author(s): Melo, Teresa M. V. D. Pinho e ; Soares, Maria I. L. ; Barbosa, Dália M. ; Gonsalves, António M. d'A. Rocha ; Beja, Ana Matos ; Paixão, José A. ; Silva, Manuela Ramos ; Veiga, Luiz Alte da
• Date: 2000
• Persistent ID: http://hdl.handle.net/10316/5244
• Origin: Estudo Geral - Universidade de Coimbra
• Document Type: Article
• Language: English

Description

(5R)-3-Methyl-5-phenyl-5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olate was generated in the presence of a range of dipolarophiles. The intermolecular 1,3-dipolar cycloaddition of this mesoionic species led to the synthesis of chiral 1H-pyrrolo[1,2-c]thiazole derivatives 7a, 7b, 8, 14, 18, 19 and 20. In the reaction with methyl and ethyl vinyl ketone, spiro compounds 9 and 15 were also obtained. The structure of compound 15 was determined by X-ray crystallography. http://www.sciencedirect.com/science/article/B6THR-407GGNF-K/1/23c3db756f6ed9f6caefffc1d46ba51a