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Molecules 2013, 18(5), 5697-5705; doi:10.3390/molecules18055697
Article

A Novel Multi-Component Reaction to Imidazo[4,5-g]-quinazolines

1,†,* , 1,†
,
1
 and
2,*
1 Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, 1 Xian Nong Tan Street, Beijing 100050, China 2 Tsinghua-Peking Center for Life Sciences and Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Haidian District, Beijing 100084, China These authors contributed equally to this work.
* Authors to whom correspondence should be addressed.
Received: 19 April 2013 / Revised: 8 May 2013 / Accepted: 10 May 2013 / Published: 16 May 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

The trace impurities discovered after extended storage of a 5-amino- benzimidazole library were determined as imidazo[4,5-g]quinazoline derivatives by extensive spectroscopic data analysis. The formation of this highly aromatic heterocyclic ring involved a novel multi-component reaction, using which several novel compounds were prepared. Its mechanism was deduced as a cascade of chemical transformations, including the formation of a Schiff’s base, intramolecular hetero-Diels-Alder reaction, defluorination and dehydrogenation.
Keywords: multi-component reaction; heterocyclic compounds; imidazo[4,5-g]-quinazoline; structure determination; hetero Diels-Alder reaction multi-component reaction; heterocyclic compounds; imidazo[4,5-g]-quinazoline; structure determination; hetero Diels-Alder reaction
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Li, L.; Zhang, Q.; Liu, B.; Liu, G. A Novel Multi-Component Reaction to Imidazo[4,5-g]-quinazolines. Molecules 2013, 18, 5697-5705.

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