Journals / Turkish Journal of Chemistry / 2013 / Cilt: 37 - Sayı: 2
Ionic liquid mediated synthesis, reactions, and insecticidal activity of 1-[(1H-benzoimidazol-2-yl)amino]spiro[azetidine-4,4 -[4 H ]chroman]-2-ones
- Journal
- Turkish Journal of Chemistry
- Pages
- 239–251
- DOI
- —
Abstract
Ionic liquid mediated synthesis of novel heterocyclic compounds 1-[(1H-benzoimidazol-2-yl)amino]-2'-phenylspiro[azetidine- 4,4'-[4'H]chroman]-2-ones (3) and 1-[(1H-benzoimidazol-2-yl)amino]- 3-chloro-2'-phenylspiro[aze tidine-4,4'-[4'H] chroman]-2-ones (4) was accomplished by condensing substituted 2-hydrazino benzimidazole (1), flavanone (2), and acetyl chloride/chloroacetyl chloride in ionic liquid, [bmim]PF6 with or without using catalyst in excellent yield (90%--95%). Further, compounds 3 and 4 were acylated with trifluoroacetic anhydride to give N-acylated products (5 and 10); 3 when treated with HCHO and (C2H5)2NH gave Mannich bases (6) and with aldehydes afforded 3-arylidene-2-azetidinone (7). Compounds 4 underwent nucleophilic substitution with (i) KI (Finkelstein reaction) and (ii) phenols to give the corresponding iodo and phenoxy derivatives (8 and 9). The synthesized compounds were characterized by analytical and spectral (IR, 1 H NMR, 13C NMR, and HRMS) data and evaluated for insecticidal activity against Periplaneta americana using cypermethrin as standard and found to exhibit excellent results.
Özet
Ionic liquid mediated synthesis of novel heterocyclic compounds 1-[(1H-benzoimidazol-2-yl)amino]-2'-phenylspiro[azetidine- 4,4'-[4'H]chroman]-2-ones (3) and 1-[(1H-benzoimidazol-2-yl)amino]- 3-chloro-2'-phenylspiro[aze tidine-4,4'-[4'H] chroman]-2-ones (4) was accomplished by condensing substituted 2-hydrazino benzimidazole (1), flavanone (2), and acetyl chloride/chloroacetyl chloride in ionic liquid, [bmim]PF6 with or without using catalyst in excellent yield (90%--95%). Further, compounds 3 and 4 were acylated with trifluoroacetic anhydride to give N-acylated products (5 and 10); 3 when treated with HCHO and (C2H5)2NH gave Mannich bases (6) and with aldehydes afforded 3-arylidene-2-azetidinone (7). Compounds 4 underwent nucleophilic substitution with (i) KI (Finkelstein reaction) and (ii) phenols to give the corresponding iodo and phenoxy derivatives (8 and 9). The synthesized compounds were characterized by analytical and spectral (IR, 1 H NMR, 13C NMR, and HRMS) data and evaluated for insecticidal activity against Periplaneta americana using cypermethrin as standard and found to exhibit excellent results.