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The synthesis of 1 H ‐benzimidazole derivatives containing a 9 H ‐xanthene or 9 H ‐thioxanthene ring
Author(s) -
Okabayashi Ichizo,
Fujiwara Hidetoshi
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210533
Subject(s) - chemistry , xanthene , benzimidazole , oxidizing agent , acetic acid , hydrogen peroxide , medicinal chemistry , acetone , ring (chemistry) , methylene , organic chemistry
2‐(9 H ‐Xanthen‐9‐ylmethyl)‐1 H ‐benzimidazole ( 2a ) was prepared by condensing 9 H ‐xanthene‐9‐acetic acid ( 1a ) with 1,2‐benzenediamine. Similarly, 2‐(9 H ‐thioxanthen‐9‐ylmethyl)‐1 H ‐benzimidazole ( 2b ) and its S,S ‐dioxide ( 2d ) were obtained. Compound 2d was also prepared by oxidizing 2b with hydrogen peroxide in acetic acid. Heating of 9 H ‐thioxanthene‐9‐acetic acid 10‐oxide ( 1c ) with 1,2‐benzenediamine gave 9‐methylene‐9 H ‐thioxanthene ( 3 ). 2‐(9 H ‐Thioxanthen‐9‐ylmethyl)‐1 H ‐benzimidazole S ‐oxide ( 2c ) was obtained by oxidizing 2b with m ‐chloroperbenzoic acid in acetone.