Synthesis of spiro-fused (C5)-pyrazolino-(C6)-triazinones, a new heterocyclic system

被引：14
|
作者：
Karpenko, Alexander V. [1 ]
Kovalenko, Sergey I. [1 ]
Shishkin, Oleg V. [2 ]
机构：
[1] Zaporozhye State Med Univ, Dept Pharmaceut Chem, UA-69035 Zaporozhe, Ukraine
[2] Natl Acad Sci Ukraine, STC Inst Single Crystals, UA-61001 Kharkov, Ukraine
来源：
TETRAHEDRON | 2009年 / 65卷 / 31期
关键词：
Heterocyclization; Rearrangement; Spiro-heterocycle; 1,2,4-Triazino[2,3-c]quinazoline; X-ray analysis; DERIVATIVES; AGENTS;
D O I：
10.1016/j.tet.2009.05.091
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reaction of 4-hydrazinoquinazoline with 2,4-diketoesters gives the corresponding 3-acylmethyl-2H[1,2,4]triazino[2,3-c]quinazolin-2-ones in a one-step procedure via cyclocondensation-Dimroth-like rearrangement. Spectroscopic studies as well as X-ray analysis reveal that the obtained triazinoquinazolines exist in their ketoimine tautomeric form. Treatment of these compounds with hydrazine hydrate affords 3'-(2-aminophenyl)-3-(het)aryl-spiro[pyrazoline-5,6'(1'H)-1,2,4-triazin]-5'(4'H)-ones or 5-(het)arylpyrazole-3-carboxylic acid hydrazides depending on the reaction conditions. The structure of the spiro-heterocycles was elucidated by means of single-crystal X-ray analysis and confirmed by spectroscopic investigations. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5964 / 5972
页数：9
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