STUDIES ON FLUORINE CONTAINING HETEROCYCLIC-COMPOUNDS .4. REACTIONS OF 3-NITRO-4-CHLOROBENZOTRIFLUORIDE AND 3,5-DINITRO-4-CHLOROBENZOTRIFLUORIDE WITH 5-MEMBERED HETEROCYCLES

The reactions of 3-nitro-4-chlorobenzotrifluoride (1a) and 3, 5-dinitro-4-chlorobenzotrifluoride (1b) with heterocycles (2-5) are described. Six S-linked and N-substituted heterocycles (6, 9-11, 13), such as 2-(2-nitro-4-trifluoromethylphenylthio) benzothiazole (9a), were prepared from the reactions of 1a with benzotriazole (2), 2-mercaptobenzothiazole (5a) and 2-mercaptobenzoxazole (5b) and from the reactions of 1b with 2. 1, 2, 4-triazole (3) and 5a in DMF respectively, 1a reacted with 2-mercaptothiazoline (4) to give desired product 7 and bis(2-nitro-4-trifluoromethylphenyl) thioether (8). 3-(2-Benzoxazolyl)-2-benzoazolinethione (15) was obtained from the reaction of 1b with 5b. The spectral data and elemental analyses were fully in accord with the proposed structures, and the possible mechanisms for these compounds and other by-products were discussed. © 1990, Taylor & Francis Group, LLC. All rights reserved.