Ionic liquid mediated synthesis, reactions, and insecticidal activity of 1-[(1H-benzoimidazol-2-yl)amino]spiro[azetidine-4,4 -[4 H ]chroman]-2-ones

Kanti SHARMA; Renuka JAIN

doi:https://doi.org/10.3906/kim-1206-47

Article Details

Ionic liquid mediated synthesis, reactions, and insecticidal activity of 1-[(1H-benzoimidazol-2-yl)amino]spiro[azetidine-4,4 -[4 H ]chroman]-2-ones

Authors:

Kanti SHARMA | Renuka JAIN

Publisher:

TUBITAK

Main Topics:

Chemistry and allied sciences

Journal:

Turkish Journal of Chemistry 2013 Vol.37 Issue 2, pp.239-251

Document Type:

Article

Publication Date:

1/2013

Document Language:

English

Document ID (Org No.):

2000727457

Frequency:

Bimonthly

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/kim-1206-47

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.

 

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.

Article Details

Ionic liquid mediated synthesis, reactions, and insecticidal activity of 1-[(1H-benzoimidazol-2-yl)amino]spiro[azetidine-4,4 -[4 H ]chroman]-2-ones

Authors: Kanti SHARMA | Renuka JAIN

Publisher: TUBITAK

Main Topics: Chemistry and allied sciences

Journal: Turkish Journal of Chemistry 2013 Vol.37 Issue 2, pp.239-251

Document Type: Article

Publication Date: 1/2013

Document Language: English

Document ID (Org No.): 2000727457

Frequency: Bimonthly

eISSN: 1303-6130

pISSN: 1300-0527

DOI: https://doi.org/10.3906/kim-1206-47

Issues

Authors:

Kanti SHARMA | Renuka JAIN

Publisher:

TUBITAK

Main Topics:

Chemistry and allied sciences

Journal:

Turkish Journal of Chemistry 2013 Vol.37 Issue 2, pp.239-251

Document Type:

Article

Publication Date:

1/2013

Document Language:

English

Document ID (Org No.):

2000727457

Frequency:

Bimonthly

eISSN:

1303-6130

pISSN:

1300-0527

DOI:

https://doi.org/10.3906/kim-1206-47