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Synthesis of A4-Thiazolines

The mechanism of this cyclization is similar to that proposed for the Hantzsch synthesis. Hydroxythiazoline intermediates have been isolated which, on heating with dilute HC1, lead to A4-thiazoline-2-thione. The precise control of the pH during the reaction permits the isolation of an acyclic intermediate (248) which is in equilibrium with its cyclic isomer (249 Scheme 182). The large influence of steric effects on the 3-position has been demonstrated with R4 = Me and R3 = Bu dealkylation at nitrogen is observed upon dehydration of the intermediate thiazoline (Scheme 183) (67BSF1948). [Pg.299]

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Thiazoline

Thiazoline synthesis

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