Synthesis of mesoionic[1,2,3]triazolo[5,1-d][1,2,5]triazepines / Savel'eva E.A., Rozin Y.A., Kodess M.I., Van Meervelt L., Dehaen W., Morzherin Y.Yu., Bakulev V.A. // Tetrahedron. - 2004. - V. 60, l. 25. - P. 5367-5372.

ISSN:

00404020

Type:

Article

Abstract:

Intramolecular cyclization of 1-amino-3-phenacyl-4-carbohydrazido-1,2,3- triazolium-5-olates has been shown to take place via selective interaction of the carbonyl group with the terminal amino function of the hydrazido group to form a 1,2,5-triazepine ring. Minor products, resulting from the interaction of the α-nitrogen atom of the hydrazido group with the carbonyl function, having a N-amino-pyridazine structure were also detected and isolated. A general method for the synthesis of novel mesoionic 2-amino-7-aryl-4-oxo-2,4,5,8- tetrahydro[1,2,3]triazolo[5,1-d][1,2,5]triazepin-9-ium-3-olates was developed. © 2004 Elsevier Ltd. All rights reserved.

Author keywords:

1-Amino-1,2,3-triazolium-5-olate; [1,2,3]Triazolo[1,5-a]pyrazine; [1,2,3]Triazolo[5,1-d][1,2,5]triazepine; Alkylation; Diazo group transfer; Fused mesoionic heterocycles

Index keywords:

ampholyte; carbonyl derivative; nitrogen; pyridazine derivative; article; atom; chemical interaction; cyclization; drug isolation; drug structure; drug synthesis; molecular interaction; priority journ

DOI:

10.1016/j.tet.2004.04.067

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https://www.scopus.com/inward/record.uri?eid=2-s2.0-2542475092&doi=10.1016%2fj.tet.2004.04.067&partnerID=40&md5=a5ea2b8e70bcea34ff66420faa1c6ec2

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Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-2542475092&doi=10.1016%2fj.tet.2004.04.067&partnerID=40&md5=a5ea2b8e70bcea34ff66420faa1c6ec2
Affiliations	Dept. Technol. and Organ. Synthesis, Urals State Technical University, 19 Mira str., 620002 Ekaterinburg, Russian Federation; Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, 20 ul. Kovalevskoi, 620219 Ekaterinburg, Russian Federation; Department of Chemistry, Laboratory of Organic Synthesis, University of Leuven, B-3001 Leuven, Belgium
Author Keywords	1-Amino-1,2,3-triazolium-5-olate; [1,2,3]Triazolo[1,5-a]pyrazine; [1,2,3]Triazolo[5,1-d][1,2,5]triazepine; Alkylation; Diazo group transfer; Fused mesoionic heterocycles
Chemicals/CAS	nitrogen, 7727-37-9
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Correspondence Address	Bakulev, V.A.; Dept. Technol. and Organ. Synthesis, Urals State Technical University, 19 Mira str., 620002 Ekaterinburg, Russian Federation; email: vasiliy.bakulev@toslab.com
CODEN	TETRA
Language of Original Document	English
Abbreviated Source Title	Tetrahedron
Source	Scopus