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Molecules 2016, 21(12), 1646; doi:10.3390/molecules21121646

A Simple Precursor for Highly Functionalized Fused Imidazo[4,5-b]pyridines and Imidazo[4,5-b]-1,8-naphthyridine

1
Chemistry Department, College of Science, IMSIU (Al-Imam Mohammad Ibn Saud Islamic University), Riyadh 11623, Saudi Arabia
2
Photochemistry Department, National Research Centre, Cairo 12622, Egypt
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 23 September 2016 / Revised: 21 November 2016 / Accepted: 23 November 2016 / Published: 1 December 2016
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [936 KB, uploaded 1 December 2016]   |  

Abstract

1-alkyl aryl-5-amino-4-(cyanoformimidoyl)imidazoles 4 were reacted with malononitrile and 2-amino-1,1,3-propenetricarbonitrile under mild experimental conditions, which led to 5-amino-3-(substituted benzyl)-6,7-dicyano-3H-imidazo[4,5-b]pyridines 5 and 6,8-diamino-3-(4-substituted benzyl)-3H-imidazo[4,5-b]-1,8-naphthyridine-7,9-dicarbonitrile 6, respectively, when the reaction was carried out in the absence of a base, or to 5,7-diamino-3-(4-alkyl aryl)-3H-imidazo[4,5-b]pyridine-6-carbonitrile 8, and 6,8,9-triamino-3-(4-substitutedbenzyl)-3H-imidazo[4,5-b]-1,8-naphthyridine-7-carbonitrile 10 in the presence of 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU). Both reactions evolved from an adduct formed by nucleophilic attack of the malononitrile anion or 2-amino-1,1,3-propenetricarbonitrile anion to the carbon of the cyanoformimidoyl substituent. In the case of the malononitrile anion, a 5-amino-1-alkyl aryl-4-(1-amino-2,2-dicyanovinyl)imidazole 7 was isolated when this reaction was carried out in the presence of DBU. The structure of compound 7 was confirmed by spectroscopic methods, and cyclized intramolecularly to 8 by heating in ethanol/triethyl amine. View Full-Text
Keywords: imidazo[4,5-b]pyridine; diaminomaleonitrile; carbon acid; imidazo[4,5-b]-1,8-naphthyridine; malomonitrile; 2-amino-1,1,3-propenetricarbonitrile imidazo[4,5-b]pyridine; diaminomaleonitrile; carbon acid; imidazo[4,5-b]-1,8-naphthyridine; malomonitrile; 2-amino-1,1,3-propenetricarbonitrile
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Al-duaij, O.K.; Zaki, M.E.; El Gazzar, A.-R.B.A. A Simple Precursor for Highly Functionalized Fused Imidazo[4,5-b]pyridines and Imidazo[4,5-b]-1,8-naphthyridine. Molecules 2016, 21, 1646.

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