Microwave-assisted One-pot Synthesis of Two Derivatives of Indenobenzoquinoxaline under Solvent Free Conditions
Journal Title: International Journal of Research in Chemistry and Environment (IJRCE) - Year 2012, Vol 2, Issue 4
Abstract
Multi component processes have emerged as powerful tools for delivering the molecular diversity need in combinatorial approaches for the synthesis of bioactive compounds thereby creating diverse chemical libraries of drug-like molecules or biological screening. Additionally, the prospect of extending one-pot reactions into combinatorial and solid-phase synthesis promises many opportunities for developing novel lead structures for pharmaceuticals, catalysts and even novel molecule based materials Quinoxaline and its derivatives are an important class of benzoheterocycles displaying a broad spectrum of biological activities which have made them privileged structures in pharmacologically active compounds. They have also found applications as building blocks in the synthesis of organic semiconductors, rigid subunits in macrocyclic receptors or molecular recognition,6 and chemically controllable switches. A microwave assisted one-pot three-component procedure was introduced for preparation of two potentially biologically important of indenobenzoquinoxaline derivatives under solvent free conditions. The reactions were completed within five minutes and the products were simply obtained in good to high yields. The multi component reaction described herein provides a simple and direct entry a number of interesting novel pyrroles. Indenobenzoquinoxaline generated in situ from ninhydrin and naphthalene-2,3-diamine, catalysed by montmorillonite K10 under microwave irradiation, condence with 4-hydroxyproline to produce 11-(1Hpyrrol-1-yl)-11H-indeno[2,1-b]benzo[g]quinoxaline in good yields. compounds and its structure was unambiguously characterized on the basis of its IR, 1 H NMR, 13C NMR spectroscopy. 1 2 3 OH OH O O N N + H2 N H2 N MW (125-130 °C), 3min CN NC CH2 (CN)2 , (1.2 eq.) DMSO (3 drops) Figure 1: Microwave assisted one-pot three-component synthesis of 2-(11H indeno[2,1- b]benzo[g]quinoxalin-11-ylidene)malononitrile 3
Authors and Affiliations
Taherkhani Mahboubeh
Keywords
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