Intermolecular Dipolar Cycloaddition Reactions of 5H,7H-Thiazolo[3,4-c]oxazol-4-ium-1-olates

✍ Scribed by Teresa M.V.D. Pinho e Melo; Maria I.L. Soares; Dália M. Barbosa; António M.d'A. Rocha Gonsalves; Ana Matos Beja; José A. Paixão; Manuela Ramos Silva; Luiz Alte da Veiga

• Book ID: 104202659
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 146 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00243-x

✦ Synopsis

AbstractÐ(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.