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Synthesis of Some New Heterocycles Derived from Phenylacetyl Isothiocyanate
Author(s) -
HEMDAN M. M.,
FAHMY A. F.,
ALI N. F.,
HEGAZI E.,
ABDELHALEEM A.
Publication year - 2008
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200890074
Subject(s) - chemistry , hydrazine (antidepressant) , derivative (finance) , acetonitrile , benzoxazole , anthranilic acid , isothiocyanate , benzothiazole , phenyl isothiocyanate , medicinal chemistry , hydrate , paraformaldehyde , acetone , organic chemistry , chromatography , financial economics , economics
Phenylacetyl isothiocyanate ( 1 ) was reacted with benzoyl hydrazine ( 2a ) in acetonitrile to give thiosemicarbazide derivative 3 which was cyclized by polyphosphoric acid to give 1,2,4‐triazoline‐5‐thione derivative 4 . Treatment of 1 with thiosemicarbazide ( 2b ) yielded another 1,2,4‐triazoline‐5‐thione derivative 5 . Similar treatment of 1 with phenyl hydrazine ( 2c ) in acetonitrile gave a differently substituted 1,2,4‐triazoline‐5‐thione derivative 6 in one pot‐reaction. On the other hand, when the reaction was carried out in acetone, a mixture of 6 and thiadiazolidine derivative 7 was obtained. However, reaction of 1 with hydrazine hydrate ( 2d ) gave hydrazine derivative 8 . Reaction of isothiocyanate 1 with anthranilic acid ( 9 ) gave benzo[ d ][1,3,6]oxazin‐1‐one derivative 10 . Treatment of 1 with 2‐aminothiophenol ( 11a ), 2‐aminophenol ( 11b ) or o ‐phenylenediamine ( 11c ) produced benzothiazole derivative 12a , benzoxazole derivative 12b and benzimidazole derivative 12c , respectively. The structures of all the products were confirmed by micro‐analytical and spectral data.