Cycloaddition reactions of 3-aryl-5-phenyl-5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olates

• Main Author: Melo, Teresa M. V. D. Pinho e
• Publication Date: 2002
• Other Authors: Gomes, Clara S. B., Gonsalves, António M. d'A. Rocha, Paixão, José A., Beja, Ana M., Silva, Manuela Ramos, Veiga, Luiz Alte da
• Format: Article
• Language: eng
• Source: Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
• Download full: https://hdl.handle.net/10316/5185; https://doi.org/10.1016/S0040-4020(02)00463-5
• topic: dipolar cycloaddition; münchnones; 1H,3H-pyrrolo[1,2-c]thiazoles

Intermolecular 1,3-dipolar cycloaddition of (5R)- and (5S)-3,5-diphenyl-5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olates, (5R)- and (5S)-3-(p-methoxyphenyl)-5-phenyl-5H,7H-thiazolo-[3,4-c]oxazol-4-ium-1-olates with a range of dipolarophiles is described. New chiral 5-aryl-3-phenyl-1H,3H-pyrrolo[1,2-c]thiazoles with R and S configuration were obtained. The structure of methyl (3R)-3-phenyl-5-(p-methoxyphenyl)-1H,3H-pyrrolo[1,2-c]thiazole-6-carboxylate was determined by X-ray crystallography. The synthesis of 7,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazole-6,7-dicarboxylates was also achieved.