DMAP catalyzed synthesis of some new pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines

DMAP catalyzed synthesis of some new pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines Starting from 2-amino-1-methyl-4,5-diphenyl-1H-pyrrole-3-carbonitrile, the synthesis of some new tricyclic pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines catalyzed by 4-(N,N-dimethylamino)pyridine (DMAP) is described. Room-temperature reaction of 2-amino-1-methyl-4,5-diphenyl-1H-pyrrole-3-carbonitrile with triethyl orthoesters afforded the corresponding imidic esters. Treatment of these compounds with hydrazine hydrate at room temperature gave 4-imino-3H-pyrrolo[2,3-d]pyrimidin-3-amines, which were subsequently cyclized to the titled compounds on heating with acyl chlorides in the presence of DMAP as catalyst under solvent-free conditions. All synthetic compounds were characterized on the basis of their spectral and microanalytical data. The NOE and NOESY experiments on one of the final products show that no Dimroth rearrangement has occurred in compounds 4-imino-3H-pyrrolo[2,3-d]pyrimidin-3-amines under the reaction conditions. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

DMAP catalyzed synthesis of some new pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines

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Publisher
Springer Netherlands
Copyright
Copyright © 2014 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-014-1697-3
Publisher site
See Article on Publisher Site

Abstract

Starting from 2-amino-1-methyl-4,5-diphenyl-1H-pyrrole-3-carbonitrile, the synthesis of some new tricyclic pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines catalyzed by 4-(N,N-dimethylamino)pyridine (DMAP) is described. Room-temperature reaction of 2-amino-1-methyl-4,5-diphenyl-1H-pyrrole-3-carbonitrile with triethyl orthoesters afforded the corresponding imidic esters. Treatment of these compounds with hydrazine hydrate at room temperature gave 4-imino-3H-pyrrolo[2,3-d]pyrimidin-3-amines, which were subsequently cyclized to the titled compounds on heating with acyl chlorides in the presence of DMAP as catalyst under solvent-free conditions. All synthetic compounds were characterized on the basis of their spectral and microanalytical data. The NOE and NOESY experiments on one of the final products show that no Dimroth rearrangement has occurred in compounds 4-imino-3H-pyrrolo[2,3-d]pyrimidin-3-amines under the reaction conditions.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Jun 4, 2014

References

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