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Heterocyclic systems containing bridgehead nitrogen atom: Part LXVI. Studies of orientation of cyclization in the synthesis of 8-fluorothiazolo[3,2-a]benzimidazol-3(2H)-one by Rajinder Dahiya; H.K. Pujari is a Chemistry article available to read on EtoBox.

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2-Fluoro-6-nitroaniline, obtained by nitration of 2-fluoroacetanilide, on reduction with Raney nickel and hydrazine hydrate followed by treatment of the resulting diamine with carbon disulphide in situ gives 4-fluorobenzimidazolyl-2-thione. This throne on condensation with chloroacetic acid gives 4-fluorobenzimidazol-2-thiolacetic acid which on cyclization with a mixture of acetic anhydride and pyridine furnishes 8-fluorothiazolo[3,2-a]benzimidazol-3(2I3)-one and not the alternate possible isomer, S-fluorothiazolo[3,2-a]benzimidazol-3(2&I)-one as revealed by 1 H-NMR spectroscopy The condensation of 4-fluorobenzimidazolyl-2-thione with 1,2-dibromoethane yields 2,3-dihydro-8-fluorothiazolo[3,2-&enzimidazole and D\_-bis-(4-fluorobenzimidazol-2-ylmercapto)ethane

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Author

Rajinder Dahiya; H.K. Pujari

Publisher

Elsevier Science; Elsevier ; Elsevier BV (ISSN 0022-1139)

Published

1989

Language

EN

Field

Chemistry (Physical Sciences)