New mesoionic compounds (2H, 3H-thiazolo[3,2-c]oxazol-7-ones) (β) or ketenes ((3-acyl-1,3-thiazolidin-2-ylidene)methanone) (β′) were generated from N-acetyl and N-benzoyl-thiazolidine-2-carboxylic acids (7a,b) using different methods, and their reactivity towards N-(phenylmethylene) benzenesulfonamide (2) and N-(phenylmethylene)aniline (3) was tested. When (7a,b) were treated with (2) and acetic anhydride in refluxing toluene solution, only imidazo[5,1-b]thiazoles (8a,b) were obtained from the mesoionic compound intermediates (β). When the ketene intermediates (β′) were generated from (7a,b) by means of Mukaiyama's reagent, only spiro-β- lactams (9a,b) were isolated.

Synthesis of imidazo[5,1-b]thiazoles or spiro-beta-lactams by reaction of imines with mesoionic compunds or ketenes generated from N-acyl-thiazolidine-2-carboxylic acids / G. Cremonesi, P. Dalla Croce, C. La Rosa. - In: TETRAHEDRON. - ISSN 0040-4020. - 60:1(2004), pp. 93-97.

Synthesis of imidazo[5,1-b]thiazoles or spiro-beta-lactams by reaction of imines with mesoionic compunds or ketenes generated from N-acyl-thiazolidine-2-carboxylic acids

G. Cremonesi
Primo
;
P. Dalla Croce
Secondo
;
C. La Rosa
Ultimo
2004

Abstract

New mesoionic compounds (2H, 3H-thiazolo[3,2-c]oxazol-7-ones) (β) or ketenes ((3-acyl-1,3-thiazolidin-2-ylidene)methanone) (β′) were generated from N-acetyl and N-benzoyl-thiazolidine-2-carboxylic acids (7a,b) using different methods, and their reactivity towards N-(phenylmethylene) benzenesulfonamide (2) and N-(phenylmethylene)aniline (3) was tested. When (7a,b) were treated with (2) and acetic anhydride in refluxing toluene solution, only imidazo[5,1-b]thiazoles (8a,b) were obtained from the mesoionic compound intermediates (β). When the ketene intermediates (β′) were generated from (7a,b) by means of Mukaiyama's reagent, only spiro-β- lactams (9a,b) were isolated.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/143838
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