18th Iranian Chemistry Congress , 2015-08-30

Title : ( Synthesis of new derivatives of 5-amino-9H-pyrrolo[2,3-e][1,2,4]triazolo[4,3c]pyrimidine via Leimgruber and Batcho indole synthesis )

Authors: neda haghir , Mehdi Bakavoli , Ali Shiri , ,

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Abstract

Background Leimgruber and Batcho indole synthesis as a very efficient tool involves condensation of onitrotoluene derivatives with DMFDMA as formamide acetals, followed by reduction of trans-βdimethylamino-2-nitrostyrene to furnish indole derivatives [1,2]. Also, pyrrolopyrimidines and related fused heterocyclic compounds have attracted the attention of numerous researchers due to their important biological activities [3]. Methods: 6-Methyl-5-nitropyrimidine-2,4(1H,3H)-dione (1) was prepared and treated with DMFDMA to obtain (E)-6-(2-(dimethylamino)vinyl)-5-nitropyrimidine-2,4(1H,3H)-dione. Afterwards, it was further cyclized through the reduction of nitro group with iron and chlorination of the latter was carried out using POCl 3 in order to give compound (2). It was treated subsequently with hydrazine hydrate and triethylorthoformate to obtain the desired compound (3). The reaction of compound (3) with various secondary amines led to the formation of new derivatives of pyrrolotriazolopyrimidine (4a-d). Results: The structures of all new synthesized compounds were confirmed by recording their spectral and micro-analytical data. For example the IR spectrum of compound 4 exhibited the stretching vibration band at 3159 cm -1 due to vibrations of NH group. The 408 1 H NMR spectrum of (4) showed two singlet signals at δ 6.74 and 8.12 ppm belonging to vinyl hydrogens of pyrrole moiety and a singlet signal at δ 12.78 ppm corresponded to the hydrogen of NH which was removed on adding D 2 O. Conclusion: New derivatives of 5-amino-9H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-c]pyrimidine via Leimgruber and Batcho indole synthesis was successfully accomplished. Keywords: Pyrrolopyrimidine; Leimgruber and Batcho; DMFDMA, Heterocyclization References [1] Clark, R. D., Repke. D. B., Heterocycles, 1984, 22, 195-221. [2] Abdulla, R. F., Brinkmeyer, R. S. Tetrahedron 1979, 35, 1675-1735. [3] Miles, R. W., Tyler, P. C., Furneaux, R. H., Bagdassarian, C. K., Schramm, V. L. Biochemistry 1998, 37, 86158621.

Keywords

, 5-amino-9H-pyrrolo[2, 3-e][1, 2, 4]triazolo[4, 3c]pyrimidineو Leimgruber and Batcho indole synthesis
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@inproceedings{paperid:1049281,
author = {Haghir, Neda and Bakavoli, Mehdi and Shiri, Ali and , },
title = {Synthesis of new derivatives of 5-amino-9H-pyrrolo[2,3-e][1,2,4]triazolo[4,3c]pyrimidine via Leimgruber and Batcho indole synthesis},
booktitle = {18th Iranian Chemistry Congress},
year = {2015},
location = {سمنان, IRAN},
keywords = {5-amino-9H-pyrrolo[2;3-e][1;2;4]triazolo[4;3c]pyrimidineو Leimgruber and Batcho indole synthesis},
}

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%0 Conference Proceedings
%T Synthesis of new derivatives of 5-amino-9H-pyrrolo[2,3-e][1,2,4]triazolo[4,3c]pyrimidine via Leimgruber and Batcho indole synthesis
%A Haghir, Neda
%A Bakavoli, Mehdi
%A Shiri, Ali
%A ,
%J 18th Iranian Chemistry Congress
%D 2015

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