From thiourea to bicyclic structures: an original route to imidazo[2,1-b]thiazoles, 5H-thiazolo[3,2-a]pyrimidines, 7H-imidazo[2,1-b][1,3]thiazines,and 2H,6H-pyrimido[2,1-b][1,3]thiazines |
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Authors: | Landreau Cyrille Deniaud David Meslin Jean Claude |
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Institution: | Laboratoire de Synthèse Organique, UMR CNRS 6513, Faculté des Sciences et des Techniques, 2 Rue de la Houssinière, 44322 Nantes Cedex 03, France. |
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Abstract: | We report an example of an efficient regioselective synthesis of biheterocyclic compounds using thiourea as starting material. In fact, N,N'-bis(dimethylaminomethylene)thiourea (1), easily prepared by double condensation of N,N-dimethylformamide dimethyl acetal with thiourea, can be reacted with haloketones or acrylic dienophiles to give thiazolic (2) and thiazinic (3) diazadienes, respectively, themselves undergoing cyclization reactions to yield imidazo2,1-b]thiazoles, 5H-thiazolo3,2-a]pyrimidines, 7H-imidazo2,1-b]1,3]thiazines, and 2H,6H-pyrimido2,1-b]1,3]thiazines without any regioisomeric ambiguity. This straightforward route represents an original and unambiguously regioselective pathway to these valuable heterocycles. |
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