Tetrahedron, volume 71, issue 21, pages 3343-3350
Thermolysis of 1-(thiophen-2-yl)-1H-tetrazoles: a route to thiophene-fused imidazoles and pyrimidines
Maria Emília Mattos Soares
1
,
Ana C F De Lyra
1
,
Marta Junqueira Henriques
2
,
J. A. Paixão
2
,
Teresa Pinho e Melo
1
Publication type: Journal Article
Publication date: 2015-05-01
Journal:
Tetrahedron
Quartile SCImago
Q2
Quartile WOS
Q3
Impact factor: 2.1
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Thermal reactions of 1-(thiophene-2-yl)-1H-tetrazoles are reported for the first time. The solution thermolysis of 1-(thiophene-2-yl)-1H-tetrazoles under conventional heating and microwave irradiation afforded the unexpected new thieno[2,3-d]pyrimidines incorporating two thiophene rings, which were obtained as major or only product. The synthesis of these heterocycles was rationalized considering the initial nitrogen elimination to generate imidoylnitrene followed by rearrangement to the corresponding carbodiimide and subsequent cyclization triggered by the nucleophilic attack of the in situ generated 2-aminothiophene. The flash vacuum pyrolysis and solution thermolysis of 1-(thiophene-2-yl)-1H-tetrazoles also gave thieno[2,3-d]imidazoles via intramolecular formal insertion into a C–C bond of the corresponding imidoylnitrene intermediate.
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Citations by publishers
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1
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3
4
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4 publications, 23.53%
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4 publications, 23.53%
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3 publications, 17.65%
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2 publications, 11.76%
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1 publication, 5.88%
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1 publication, 5.88%
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Soares M. E. M. et al. Thermolysis of 1-(thiophen-2-yl)-1H-tetrazoles: a route to thiophene-fused imidazoles and pyrimidines // Tetrahedron. 2015. Vol. 71. No. 21. pp. 3343-3350.
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Soares M. E. M., De Lyra A. C. F., Henriques M. J., Paixão J. A., Pinho e Melo T. Thermolysis of 1-(thiophen-2-yl)-1H-tetrazoles: a route to thiophene-fused imidazoles and pyrimidines // Tetrahedron. 2015. Vol. 71. No. 21. pp. 3343-3350.
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TY - JOUR
DO - 10.1016/j.tet.2015.03.102
UR - https://doi.org/10.1016/j.tet.2015.03.102
TI - Thermolysis of 1-(thiophen-2-yl)-1H-tetrazoles: a route to thiophene-fused imidazoles and pyrimidines
T2 - Tetrahedron
AU - Soares, Maria Emília Mattos
AU - De Lyra, Ana C F
AU - Henriques, Marta Junqueira
AU - Paixão, J. A.
AU - Pinho e Melo, Teresa
PY - 2015
DA - 2015/05/01 00:00:00
PB - Elsevier
SP - 3343-3350
IS - 21
VL - 71
SN - 0040-4020
SN - 1464-5416
ER -
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@article{2015_Soares,
author = {Maria Emília Mattos Soares and Ana C F De Lyra and Marta Junqueira Henriques and J. A. Paixão and Teresa Pinho e Melo},
title = {Thermolysis of 1-(thiophen-2-yl)-1H-tetrazoles: a route to thiophene-fused imidazoles and pyrimidines},
journal = {Tetrahedron},
year = {2015},
volume = {71},
publisher = {Elsevier},
month = {may},
url = {https://doi.org/10.1016/j.tet.2015.03.102},
number = {21},
pages = {3343--3350},
doi = {10.1016/j.tet.2015.03.102}
}
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Soares, Maria Emília Mattos, et al. “Thermolysis of 1-(thiophen-2-yl)-1H-tetrazoles: a route to thiophene-fused imidazoles and pyrimidines.” Tetrahedron, vol. 71, no. 21, May. 2015, pp. 3343-3350. https://doi.org/10.1016/j.tet.2015.03.102.