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Title: | Synthesis of Chiral Pyrrolo[1,2-c]thiazoles via Intramolecular Dipolar Cycloaddition of Münchnones: An Interesting Rearrangement to Pyrrolo[1,2-c]thiazines | Authors: | Melo, Teresa M. V. D. Pinho e Soares, Maria I. L. Gonsalves, António M. d'A. Rocha Paixão, José A. Beja, Ana M. Silva, Manuela Ramos Veiga, Luiz Alte da Pessoa, João Costa |
Issue Date: | 14-Jun-2002 | Publisher: | American Chemical Society | Citation: | The Journal of Organic Chemistry. 67:12 (2002) 4045-4054 | Abstract: | Intramolecular dipolar cycloaddition of bicyclic münchnones, 5H,7H-thiazolo[3,4-c]oxazol-4-ium-1-olates, derived from cyclodehydration of 2-substituted-N-acylthiazolidine-4-carboxylic acids are reported. A range of new pyrrolo[1,2-c]thiazole derivatives (7, 14, 15, 20, 23, and 26) were obtained as single enantiomers from 2-phenylthiazolidines, 2-benzoylthiazolidines, and 2-methylthiazolidine-4-carboxylates. Pyrrolo[1,2-c][1,4]thiazine derivative 27 was also obtained from pyrrolo[1,2-c]thiazole derivative 26. The structures of methyl (2R,4R)-2-(p-methoxybenzoyl)thiazolidine-4-carboxylate (17a), methyl (2R,4R)-2-(p-methoxybenzoyl)-N-(prop-2-ynyloxyacetyl)thiazolidine- 4-carboxylate (18), and 3-oxo-4-phenyl-3,4,6,8-tetrahydro-1H-furo[3‘,4‘:2,3]pyrrolo[1,2-c][1,4]thiazine (27) were determined by X-ray crystallography. Chirooptical studies of the pyrrolo[1,2-c]thiazoles were done by confirming the absolute configuration at the chiral center C-3. | URI: | https://hdl.handle.net/10316/10281 | ISSN: | 0022-3263 | DOI: | 10.1021/jo010807p | Rights: | openAccess |
Appears in Collections: | FCTUC Física - Artigos em Revistas Internacionais FCTUC Química - Artigos em Revistas Internacionais |
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