Synthesis of some Fused Heterocyclic Compounds from α-Bromo Tetralone and Indanone

Akram N Mohammad,Ahlam M.N Yahya

doi:10.33899/rjs.2010.36837

Abstract

A number of heterocyclic compounds (7-14) were prepared by the reaction of α- bromo ketones (3,4) with 2-amino-5-phenyl-1,3,4(thiadiazole or oxadiazole) and 5-phenyl- 1,3,4-triazole-2-thiol. Moreover, on heating under reflux of α-bromo ketones (3,4) in the presence of ethanol with thiazole derivatives (5,6) (was prepared from the reaction of α- bromo ketone (3,4) with thiourea), compounds (7,8) were obtained. The structure of the synthesized compounds have been elucidated by their physical and spectral methods .

Highlights

Tetralones and indanones are compounds which are very important as intermediate products for synthesizing various medicinal starting materials such as steroids (House et al, 1960; Brown et al.,1981), serotonin pre-synaptic inhibitor compounds with antidepressant activity (Johnson and Doub, 1999), non-steroidal anti-infllamatory (NSAIDs) drugs (Brunel et al, 1995) and for the treatment of Alzheimer,s disease (Sayena et al, 2003)
Therefor, many investigators reported the synthesis of this type of compounds (Magnus et al, 2006; Jasinski et al, 2006; Davood et al, 2007; Shieh and Mckenna, 2008)
Therefor, an attempt was made to prepare versatile fused heterocyclic compounds from tetralone and indanone owing to their practical significance

Summary

INTRODUCTION

Tetralones and indanones are compounds which are very important as intermediate products for synthesizing various medicinal starting materials such as steroids (House et al, 1960; Brown et al.,1981), serotonin pre-synaptic inhibitor compounds with antidepressant activity (Johnson and Doub, 1999), non-steroidal anti-infllamatory (NSAIDs) drugs (Brunel et al, 1995) and for the treatment of Alzheimer,s disease (Sayena et al, 2003). To a solution of (0.2 mole, 1.07gm) of thiourea in ethanol (5 ml) heated under reflux, 2bromo-1-tetralone or indanone (3,4) (0.1 mole, 3 gm) in ethanol (15 ml) was added during (1.5 hrs), heating was continued for (15 min.) This crude reaction mixture was cooled and extracted with ether to remove unreacted ketone. Synthesis of fused 1,3,4-thiadiazole derivatives (9,10) : (King and Hlavacek, 1950) To a solution of α-bromo ketone (3,4) (0.01 mole) in ethanol (40 ml), 2-amino-5-. Synthesis of fused 1,3,4-triazole derivatives (11,12) : ( Wiley et al, 1951) To a solution of α-bromo ketone (3,4) (0.01 mole) in (40 ml) of ethanol, (0.01 mole, 1.77 gm) of 2-amino-5-phenyl-1,3,4-triazole (b) was added.

RESULTS

Br C CO

HO N