Practical synthesis of regioisomeric 5(7)-amino-6,7(4,5)-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazines

Anton V. Dolzhenko; Anna V. Dolzhenko; Wai Keung Chui

doi:10.1016/j.tet.2007.10.046

Practical synthesis of regioisomeric 5(7)-amino-6,7(4,5)-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazines

Anton V. Dolzhenko, Anna V. Dolzhenko, Wai Keung Chui

Research output: Contribution to journal › Article › Research › peer-review

38 Citations (Scopus)

Abstract

A convenient and efficient synthesis of new 5-azapurine derivatives was developed. The regioisomeric 5-amino-6,7-dihydro- and 7-amino-4,5-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazines were prepared in 3-4 steps from benzhydrazide via complementary and regiospecific routes as a part of our lead finding program. The molecular structures and tautomeric preferences of the compounds obtained were investigated using NMR spectral data and X-ray crystallography.

Original language	English
Pages (from-to)	12888-12895
Number of pages	8
Journal	Tetrahedron
Volume	63
Issue number	52
DOIs	https://doi.org/10.1016/j.tet.2007.10.046
Publication status	Published - 24 Dec 2007
Externally published	Yes

Keywords

1,2,4-Triazoles
5-Azapurines
Fused 1,3,5-triazines
Hydrazides
Tautomerism
Triazolotriazines

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10.1016/j.tet.2007.10.046

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title = "Practical synthesis of regioisomeric 5(7)-amino-6,7(4,5)-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazines",

abstract = "A convenient and efficient synthesis of new 5-azapurine derivatives was developed. The regioisomeric 5-amino-6,7-dihydro- and 7-amino-4,5-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazines were prepared in 3-4 steps from benzhydrazide via complementary and regiospecific routes as a part of our lead finding program. The molecular structures and tautomeric preferences of the compounds obtained were investigated using NMR spectral data and X-ray crystallography.",

keywords = "1,2,4-Triazoles, 5-Azapurines, Fused 1,3,5-triazines, Hydrazides, Tautomerism, Triazolotriazines",

author = "Dolzhenko, {Anton V.} and Dolzhenko, {Anna V.} and Chui, {Wai Keung}",

note = "Funding Information: This work is supported by the Academic Research Fund from the National University of Singapore (WBS R-148-000-069-112). The authors thank Tan Geok Kheng and Koh Lip Lin for the X-ray crystallography study. Copyright: Copyright 2009 Elsevier B.V., All rights reserved.",

year = "2007",

month = dec,

day = "24",

doi = "10.1016/j.tet.2007.10.046",

language = "English",

volume = "63",

pages = "12888--12895",

journal = "Tetrahedron",

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T1 - Practical synthesis of regioisomeric 5(7)-amino-6,7(4,5)-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazines

AU - Dolzhenko, Anton V.

AU - Dolzhenko, Anna V.

AU - Chui, Wai Keung

N1 - Funding Information: This work is supported by the Academic Research Fund from the National University of Singapore (WBS R-148-000-069-112). The authors thank Tan Geok Kheng and Koh Lip Lin for the X-ray crystallography study. Copyright: Copyright 2009 Elsevier B.V., All rights reserved.

PY - 2007/12/24

Y1 - 2007/12/24

N2 - A convenient and efficient synthesis of new 5-azapurine derivatives was developed. The regioisomeric 5-amino-6,7-dihydro- and 7-amino-4,5-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazines were prepared in 3-4 steps from benzhydrazide via complementary and regiospecific routes as a part of our lead finding program. The molecular structures and tautomeric preferences of the compounds obtained were investigated using NMR spectral data and X-ray crystallography.

AB - A convenient and efficient synthesis of new 5-azapurine derivatives was developed. The regioisomeric 5-amino-6,7-dihydro- and 7-amino-4,5-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazines were prepared in 3-4 steps from benzhydrazide via complementary and regiospecific routes as a part of our lead finding program. The molecular structures and tautomeric preferences of the compounds obtained were investigated using NMR spectral data and X-ray crystallography.

KW - 1,2,4-Triazoles

KW - 5-Azapurines

KW - Fused 1,3,5-triazines

KW - Hydrazides

KW - Tautomerism

KW - Triazolotriazines

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U2 - 10.1016/j.tet.2007.10.046

DO - 10.1016/j.tet.2007.10.046

M3 - Article

AN - SCOPUS:36148983442

SN - 0040-4020

VL - 63

SP - 12888

EP - 12895

JO - Tetrahedron

JF - Tetrahedron

IS - 52

ER -

Practical synthesis of regioisomeric 5(7)-amino-6,7(4,5)-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazines

Abstract

Keywords

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