Crystal structure and stereochemistry study of 2-substituted benzoxazole derivatives.

Ahmed F Mabied,Ibrahim S A Farag,Esmat El-Kholy,Naima A Ahmed,Elsayed M Shalaby,Hamdia A Zayed

doi:10.1155/2014/728343

Ahmed F Mabied, Ibrahim S A Farag + Show 4 more

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https://doi.org/10.1155/2014/728343

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Abstract

The structure of 2-[(4-chlorophenylazo) cyanomethyl] benzoxazole, C15H9ClN4O (I), has triclinic () symmetry. The structure displays N–H ⋯ N hydrogen bonding. The structure of 2-[(arylidene) cyanomethyl] benzoxazoles, C17H10N2O3 (II), has triclinic () symmetry. The structure displays C–H ⋯ N, C–H ⋯ C hydrogen bonding. In (I), the chlorophenyl and benzoxazole groups adopt a trans configuration with respect to the central cyanomethyle hydrazone moiety. Compound (II) crystallized with two molecules in the asymmetric unit shows cisoid conformation between cyano group and benzoxazole nitrogen, contrary to (I). In (II) the benzodioxole has an envelope conformation (the C17 atom is the flap atom). The molecular geometry obtained using molecular mechanics (MM) calculations has been discussed along with the results of single crystal analysis.

Highlights

IntroductionBenzoxazole derivatives are one of the most important bioactive heterocyclic organic compounds in pharmaceutical chemistry
Benzoxazole derivatives are one of the most important bioactive heterocyclic organic compounds in pharmaceutical chemistry. They have been used as a starting material for synthesis of bioactive structures of pharmaceutical drugs, such as the antibiotic Calcimycin that includes a 2-substituted benzoxazole ring in its molecular structure [1, 2]
In view of the aforementioned literature survey and to support the pharmaceutical and organic chemistry scientists with structural aspects that may be of value in designing new derivatives and potent drugs, we present the geometrical, stereochemical features of two bioactive 2-substituted benzoxazole derivatives comparing their structures with each other and related structures, using X-ray single crystal analysis and molecular mechanics (MM) calculations

Summary

Introduction

Benzoxazole derivatives are one of the most important bioactive heterocyclic organic compounds in pharmaceutical chemistry. They have been used as a starting material for synthesis of bioactive structures of pharmaceutical drugs, such as the antibiotic Calcimycin that includes a 2-substituted benzoxazole ring in its molecular structure [1, 2]. Previous studies revealed that substituted benzoxazoles possess diverse chemotherapeutic activities including antibiotic, antimicrobial, antiviral, topoisomerase inhibitors, and antitumor activities [3,4,5,6]. Benzoxazole derivatives have been entered in the synthesis of new classes of antibacterial drug, which has showed activity against bacterial infections [8]. Benzoxazoles are widely used in industry, such as a photostable highly efficient UV dyes, a dopant in organic light-emitting diodes, chromophores, and chemosensors [9, 10]

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