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Studies on the syntheses of azole derivatives. Part VIII . Photolysis of N ‐aryl‐ N ‐benzylearbamoyl azides [studies on the syntheses of heterocyclic compounds. Part CDXV
Author(s) -
Kametani Tetsuji,
Shio Masahisa
Publication year - 1971
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.5570080404
Subject(s) - chemistry , iif , azide , azole , photodissociation , aryl , medicinal chemistry , organic chemistry , alkyl , antifungal , medicine , dermatology , antibody , immunology , biology , autoantibody
Photolysis of N ‐benzyl‐ N ‐phenylearbamoylazide (IVc) afforded 1‐benzy 1‐2‐benzimidazolinone (Ic), 2‐benzimidazolinone (IIe), 4‐benzy 1‐2‐benzimidazolinone (IIe), and 5‐benzy1‐2‐benzimidazo‐linone (IIf)‐ The same reaction of N ‐benzyl‐ N ‐(4‐chlorophenyl) carbamoyl azide (IVd) gave 3‐benzyl‐1‐(phenylhydrazocarbonyl)‐2‐benzimidazolinone (VIb) besides the above four products. In the case of N ‐benzyl‐4‐(4‐butoxyphenyl)carbamoyl azide (IVe), 1‐benzy1‐5‐butoxy‐2‐benz‐imidazolinone (1e), 5‐butoxy‐2‐benzimidazolinone (IId), 5‐benzy1‐2‐benzimidazolinone (IIf), and 4‐benzy1‐6‐butoxy‐2‐benzimidazolinone (IIg).