1-(Imidazol-1-yl)-indolizines—two-step synthesis and optical properties

Rafał Matczak , Beata Koszarna , Daniel Gryko

Abstract

A one-pot process leading to complex aromatic heterocyclic compounds has been designed. Kröhnke methodology has been used to synthesize indolizines bearing an aldimino-substituent at position 1. Further reaction of these compounds with 1,2-diketones and ammonium acetate led to tetra-substituted imidazoles in 5–28% overall yield. The resulting compounds display strong absorption of UV radiation and emission of a blue light accompanied with large Stokes shifts. Replacing the aryl substituents with thiophene at position 3 of the indolizine and position 2 of the imidazole produce a further red shift of the absorption (vs products with substituted benzene rings) as a result of a more planar conformation in the ground state.
Author Rafał Matczak (FC / DOC)
Rafał Matczak,,
- Department Of Organic Chemistry
, Beata Koszarna
Beata Koszarna,,
-
, Daniel Gryko (FC / DOC)
Daniel Gryko,,
- Department Of Organic Chemistry
Journal seriesTetrahedron, ISSN 0040-4020, (A 30 pkt)
Issue year2014
Vol70
No39
Pages7006-7009
Publication size in sheets0.5
Keywords in EnglishIndolizine; Fluorescence; Heterocycles; Imidazole; Dyes
DOIDOI:10.1016/j.tet.2014.07.060
URL http://www.sciencedirect.com/science/article/pii/S0040402014010746
Languageen angielski
File
1-s2.0-S0040402014010746-main.pdf 363.19 KB
Score (nominal)30
ScoreMinisterial score = 30.0, 28-11-2017, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 28-11-2017, ArticleFromJournal
Publication indicators WoS Impact Factor: 2014 = 2.641 (2) - 2014=2.675 (5)
Citation count*2 (2016-05-09)
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