Synthesis, antioxidant and antimicrobial evaluation of thiazolidinone,

azetidinone encompassing indolylthienopyrimidines

ANAND RAGHUNATH SAUNDANE*, MANJUNATHA YARLAKATTI,

PRABHAKER WALMIK and VIJAYKUMAR KATKAR

Department of Post-Graduate Studies and Research in Chemistry, Gulbarga University,

Gulbarga-585 106, India

e-mail: arsaundane@rediff.com

Abstract. Various 2-amino-N′-{3-(2′,5′-disubstituted-1H-indol-3′-yl)methylene}-4,5-dimethylthieno-3-

carbohydrazides (3) synthesized by condensation of 2-amino-4,5-dimethyl thiophene-3-carbohydrazide (2)

with 2,5- disubstituded indole-3-carboxaldehyde (1). The Schiff’s base (3) on cyclocondensation with acetic

anhydride and triethyl orthoformate afforded thienopyrimidine analogues (4) and (7), respectively. Compounds

4 or 7 on cyclization with thioglycolic acid and chloroacetyl chloride gave thiazolidin-4-ones (5) or (8) and

azitidin-2-ones (6) or (9) respectively. The structures of these newly synthesized compounds have been established

on the basis of their spectral data and elemental analysis. Some of the compounds exhibited promising

antioxidant and antimicrobial activities.

Graphical Abstract. Several 2-substituted-5,6-diimethyl-3-[2-(2’-phenyl-5’-substituted 1H-indol-3’-yl)-

4-oxothiazolidin-3-yl]thieno[2,3-d]pyrimidin-4(3H)-ones (5 a-c and 8 a-c) and 2-

substituted-5,6-dimethyl-3-[3-chloro-2-(2’-phenyl-5’-substituted 1H-indol-3’-yl)-4-

oxoazetidin-1-yl]-thieno[2,3-d]pyrimidin-4(3H)-ones (6 a-c and 9 a-c) were

prepared and characterized by spectral studies and elemental analysis. These

compounds were screened for antioxidant and antimicrobial activities.

Keywords. Indole; thienopyrimidine; thiazolidin-4-one; azetidin-2-one; antioxidant; antimicrobial activities.