6-Bromo-1-(1,2-propadien­yl)-3-(2-propyn­yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one

The reaction of propargyl bromide and 6-bromo-1,3-dihydro­imidazo[4,5-b]pyridin-2-one in refluxing dimethyl­formamide yields the title compound, C(12)H(8)BrN(3)O, which features nitro­gen-bound propadienyl and propynyl substituents. The imidazolopyridine fused ring is planar (r.m.s. deviation = 0.01...

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Autores principales: Dahmani, S., Haoudi, A., Capet, F., Essassi, El Mokhtar, Ng, Seik Weng
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2983773/
https://www.ncbi.nlm.nih.gov/pubmed/21580600
http://dx.doi.org/10.1107/S1600536810007695
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author Dahmani, S.
Haoudi, A.
Capet, F.
Essassi, El Mokhtar
Ng, Seik Weng
author_facet Dahmani, S.
Haoudi, A.
Capet, F.
Essassi, El Mokhtar
Ng, Seik Weng
author_sort Dahmani, S.
collection PubMed
description The reaction of propargyl bromide and 6-bromo-1,3-dihydro­imidazo[4,5-b]pyridin-2-one in refluxing dimethyl­formamide yields the title compound, C(12)H(8)BrN(3)O, which features nitro­gen-bound propadienyl and propynyl substituents. The imidazolopyridine fused ring is planar (r.m.s. deviation = 0.012 Å); the propadienyl chain is coplanar with the fused ring as it is conjugated with it, whereas the propynyl chain is not as the nitro­gen-bound C atom is a methyl­ene linkage. The acetyl­enic H atom is hydrogen bonded to the carbonyl O atom of an adjacent mol­ecule, forming a helical chain runnning along the b axis.
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spelling pubmed-29837732010-12-30 6-Bromo-1-(1,2-propadien­yl)-3-(2-propyn­yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one Dahmani, S. Haoudi, A. Capet, F. Essassi, El Mokhtar Ng, Seik Weng Acta Crystallogr Sect E Struct Rep Online Organic Papers The reaction of propargyl bromide and 6-bromo-1,3-dihydro­imidazo[4,5-b]pyridin-2-one in refluxing dimethyl­formamide yields the title compound, C(12)H(8)BrN(3)O, which features nitro­gen-bound propadienyl and propynyl substituents. The imidazolopyridine fused ring is planar (r.m.s. deviation = 0.012 Å); the propadienyl chain is coplanar with the fused ring as it is conjugated with it, whereas the propynyl chain is not as the nitro­gen-bound C atom is a methyl­ene linkage. The acetyl­enic H atom is hydrogen bonded to the carbonyl O atom of an adjacent mol­ecule, forming a helical chain runnning along the b axis. International Union of Crystallography 2010-03-06 /pmc/articles/PMC2983773/ /pubmed/21580600 http://dx.doi.org/10.1107/S1600536810007695 Text en © Dahmani et al. 2010 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Dahmani, S.
Haoudi, A.
Capet, F.
Essassi, El Mokhtar
Ng, Seik Weng
6-Bromo-1-(1,2-propadien­yl)-3-(2-propyn­yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one
title 6-Bromo-1-(1,2-propadien­yl)-3-(2-propyn­yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one
title_full 6-Bromo-1-(1,2-propadien­yl)-3-(2-propyn­yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one
title_fullStr 6-Bromo-1-(1,2-propadien­yl)-3-(2-propyn­yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one
title_full_unstemmed 6-Bromo-1-(1,2-propadien­yl)-3-(2-propyn­yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one
title_short 6-Bromo-1-(1,2-propadien­yl)-3-(2-propyn­yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one
title_sort 6-bromo-1-(1,2-propadien­yl)-3-(2-propyn­yl)-1h-imidazo[4,5-b]pyridin-2(3h)-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2983773/
https://www.ncbi.nlm.nih.gov/pubmed/21580600
http://dx.doi.org/10.1107/S1600536810007695
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