Tetrahedron Letters, volume 58, issue 42, pages 3998-4002
Effective synthesis of 6-substituted 7H-tetrazolo[5,1-b][1,3,4]thiadiazines via a one-pot condensation/nitrosation/azide-tetrazole tautomerism reaction sequence
3
Higher Chemical College, Russian Academy of Sciences, 125047 Moscow, Russian Federation
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Publication type: Journal Article
Publication date: 2017-10-01
Journal:
Tetrahedron Letters
Quartile SCImago
Q3
Quartile WOS
Q3
Impact factor: 1.8
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Abstract A new, simple, and general method for the synthesis of 6-R-7 H -tetrazolo[5,1- b ][1,3,4]thiadiazines (R = Ar, Het, Alk) has been developed. The described method is based on the one-pot condensation of α-haloketones with thiocarbohydrazide, nitrosation of the formed hydrazinylthiadiazine using NaNO 2 /HCl, and intramolecular cyclization of the nitrosation product via azide-tetrazole tautomerism. Spectroscopic and structural investigations revealed that the azide-tetrazole equilibrium is completely shifted to the tetrazole form both in solution and the solid state.
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Kulikov A. et al. Effective synthesis of 6-substituted 7H-tetrazolo[5,1-b][1,3,4]thiadiazines via a one-pot condensation/nitrosation/azide-tetrazole tautomerism reaction sequence // Tetrahedron Letters. 2017. Vol. 58. No. 42. pp. 3998-4002.
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Kulikov A., Epishina M. A., Fershtat L. L., Romanova A. A., Makhova N. N. Effective synthesis of 6-substituted 7H-tetrazolo[5,1-b][1,3,4]thiadiazines via a one-pot condensation/nitrosation/azide-tetrazole tautomerism reaction sequence // Tetrahedron Letters. 2017. Vol. 58. No. 42. pp. 3998-4002.
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TY - JOUR
DO - 10.1016/j.tetlet.2017.09.014
UR - https://doi.org/10.1016%2Fj.tetlet.2017.09.014
TI - Effective synthesis of 6-substituted 7H-tetrazolo[5,1-b][1,3,4]thiadiazines via a one-pot condensation/nitrosation/azide-tetrazole tautomerism reaction sequence
T2 - Tetrahedron Letters
AU - Epishina, Margarita A.
AU - Romanova, Anna A
AU - Kulikov, Alexander
AU - Fershtat, Leonid L.
AU - Makhova, Nina N.
PY - 2017
DA - 2017/10/01 00:00:00
PB - Elsevier
SP - 3998-4002
IS - 42
VL - 58
SN - 0040-4039
SN - 1873-3581
ER -
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@article{2017_Kulikov,
author = {Margarita A. Epishina and Anna A Romanova and Alexander Kulikov and Leonid L. Fershtat and Nina N. Makhova},
title = {Effective synthesis of 6-substituted 7H-tetrazolo[5,1-b][1,3,4]thiadiazines via a one-pot condensation/nitrosation/azide-tetrazole tautomerism reaction sequence},
journal = {Tetrahedron Letters},
year = {2017},
volume = {58},
publisher = {Elsevier},
month = {oct},
url = {https://doi.org/10.1016%2Fj.tetlet.2017.09.014},
number = {42},
pages = {3998--4002},
doi = {10.1016/j.tetlet.2017.09.014}
}
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Kulikov, Alexander, et al. “Effective synthesis of 6-substituted 7H-tetrazolo[5,1-b][1,3,4]thiadiazines via a one-pot condensation/nitrosation/azide-tetrazole tautomerism reaction sequence.” Tetrahedron Letters, vol. 58, no. 42, Oct. 2017, pp. 3998-4002. https://doi.org/10.1016%2Fj.tetlet.2017.09.014.