Synthesis and Density Functional Theory Study of [1,2,3]Triazolo[4,5-d][1,2,4] Triazolo[4,3-a]Pyrimidine Derivatives: A Novel Heterocyclic System

Autor:	Ali Shiri, Kayvan Saadat, Yasaman Etemadi, Sarina Sadat Mozafari, Mehdi Bakavoli, Marzieh Akbarzadeh
Rok vydání:	2016
Předmět:	Pyrimidine 010405 organic chemistry Chemistry Stereochemistry Substitution (logic) General Chemistry Nuclear magnetic resonance spectroscopy 010402 general chemistry Ring (chemistry) 01 natural sciences 0104 chemical sciences D-1 chemistry.chemical_compound Density functional theory
Zdroj:	Journal of Chemical Research. 40:633-636
ISSN:	2047-6507 1747-5198
DOI:	10.3184/174751916x14743011878429
Popis:	Several 3H-[1,2,3]triazolo[4,5-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives of a novel ring system have been synthesised. The initial substitution of the 4-Cl function of 2,4-dichloro-6-methylpyrimidin-5-amine with benzylamine followed by treatment with sodium nitrite generated 3-benzyl-5-chloro-7-methyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine. Nucleophilic substitution of the 5-Cl moiety of the latter compound with hydrazine hydrate and subsequent treatment with carbon disulfide in boiling pyridine gave, quantitatively, the corresponding [1,2,3]triazolo[4,5-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives. Density functional theory (DFT) studies were also performed to reveal regioselectivity of the ring closure via Gauge-Independent Atomic Orbital (GIAO) 1H NMR calculations. The WP04 method was used as the DFT code to yield accurate chemical shift values. Theoretical results correlated well with the expected regioisomer and aided assignment of the final structure.
Databáze:	OpenAIRE
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