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Title: Synthesis of tricyclic isoindoles and thiazolo[3,2-c][1,3]benzoxazines
Authors: Pinho e Melo, Teresa M. V. D. 
Santos, Catarina I. A. 
Rocha Gonsalves, António M. dA. 
Paixão, José A. 
Beja, Ana M. 
Keywords: Diastereoselectivity; Thiazolo[2,3-a]isoindoles; 3-Methylene-2,5-oxazolo[2,3-a]isoindoles; [1.3]Thiazolo[3,2-c][1,3]benzoxazines
Issue Date: 2004
Citation: Tetrahedron. 60:18 (2004) 3949-3955
Abstract: The thermolysis of (3R,9bS)-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-carboxylic acids in Ac2O led to novel 3-methylene-2,5-dioxo-3H,9bH-oxazolo[2,3-a]isoindoles and chiral (9bS)-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindoles were obtained on FVP. Starting from -cysteine methyl ester (3R,10bR)-5-oxo-2,3-dihydro-10bH-[1.3]thiazolo[3,2-c][1,3]benzoxazines were obtained as single stereoisomers. The thermolysis of (3R,10bR)-5-oxo-2,3-dihydro-10bH-[1.3]thiazolo[3,2-c][1,3]benzoxazine-3-carboxylic acid in Ac2O gave 5-acetyl-2-phenyl-2,3-dihydrothiazole. The structures of methyl (3R,9bS)-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-carboxylate 1a and methyl (2R,4R)-N-chlorocarbonyl-2-(2-hydroxyphenyl)thiazolidine-4-carboxylate 9 were determined by X-ray crystallography.
Rights: openAccess
Appears in Collections:FCTUC Química - Artigos em Revistas Internacionais

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