Synthesis and Reactivity of 3′,5′-Dichloro-1H-spiro(quinazoline-2,4′-[1,2,6]thiadiazin)-4(3H)-ones

被引：8
|
作者：
Kalogirou, Andreas S. [1 ,2 ]
Kourtellaris, Andreas [2 ]
Koutentis, Panayiotis A. [2 ]
机构：
[1] European Univ Cyprus, Dept Life Sci, 6 Diogenis Str,POB 22006, CY-1516 Nicosia, Cyprus
[2] Univ Cyprus, Dept Chem, POB 20537, CY-1678 Nicosia, Cyprus
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 31-32期
关键词：
Sulfur heterocycles; Cyclization; Spirocycles; Quinazoline; Thiadiazine; ANTIFUNGAL ACTIVITY; MOLECULAR DOCKING; DERIVATIVES; CHEMISTRY; 3,4,4,5-TETRACHLORO-4H-1,2,6-THIADIAZINE; CYCLOPENTATHIADIAZINES; TETRACYANOETHYLENE; SUBSTITUTION; ACCESS; SPIRO;
D O I：
10.1002/ejoc.201900576
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A three-step synthesis of 3 ',5 '-dichloro-1H-spiro(quinazo-line-2,4 '-[1,2,6]thiadiazin)-4(3H)-ones starting from 3,4,4,5-tetra-chloro-4H-1,2,6-thiadiazine is presented. The latter reacts with 2-aminobenzonitriles to give 2-[(3,5-dichloro-4H-1,2,6-thiadiazin-4-ylid-ene)amino]benzonitriles, which affords, after hydration, the respective benzamides. Upon heating at reflux in EtOH or HFIP, the benzamides intramolecularly cyclize onto the thiadiazine C4 position to give 3 ',5 '-dichloro-1H-spiro(quinazoline-2,4 '-[1,2,6]thiadiazin)-4(3H)-ones. Single crystal X-ray crystallography supports the structure of two analogues. The chloride displacement of these new spiroquinazolinones was demonstrated by Stille coupling, and by reaction with methoxide to afford both the mono and bis-methoxy derivatives.
引用
收藏
页码：5462 / 5474
页数：13
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