1. Intermolecular cycloaddition of nonstabilized azomethine ylides generated from 1,3-thiazolidine-4-carboxylic acids: synthesis of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles
- Author
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Artur M. S. Silva, Antonio M. d'A. Rocha Gonsalves, Agnieszka Kaczor, Teresa M. V. D. Pinho e Melo, Rui Fausto, and Ana L. Cardoso
- Subjects
Thiazolidine ,Azomethine ylide ,010402 general chemistry ,Medicinal chemistry ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Drug Discovery ,Organic chemistry ,"1,3-dipolar cycloaddition" ,Thiazole ,Dimethyl acetylenedicarboxylate ,1,3-Thiazolidine-4-carboxylic acids ,010405 organic chemistry ,Condensation ,Organic Chemistry ,Intermolecular force ,General Medicine ,Cycloaddition ,3. Good health ,0104 chemical sciences ,chemistry ,1,3-Dipolar cycloaddition ,Azomethine ylides ,Stereoselectivity ,"1,3-thiazolidine-4-carboxylic acids" ,5,7a-Dihydro-1H,3H-pyrrolo[1,2-c]thiazoles ,"5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles" - Abstract
The 1,3-dipolar cycloaddition of dimethyl acetylenedicarboxylate with nonstabilized azomethine ylides, generated via the decarboxylative condensation of 1,3-thiazolidine-4-carboxylic acids with aldehydes, afforded 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazole derivatives. 2-Substituted-1,3-thiazolidine-4-carboxylic acids led to the stereoselective formation of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles. Quantum-chemistry calculations were carried out allowing the rationalization of the observed stereoselective formation of the anti-dipole. http://www.sciencedirect.com/science/article/B6THR-4KSSW69-5/1/f6fd75ae8164720ba1de8d3b3a44ed03
- Published
- 2006