Unexpected conversion of 4-oxo-4H-chromene-2-carboxylic acid to 2-(1,3-benzothiazol-2-yl)-4H-chromen-4-one and spiro[1,4-benzothiazine-2,2′-chromene]-3,4′(3′H,4H)-dione

被引：0

作者：

Cagide, Fernando ^{[1
]}

Gomes, Ligia R. ^{[2
]}

Low, John N. ^{[3
]}

Borges, Fernanda ^{[1
]}

机构：

[1] Univ Porto, CIQUP Dept Chem & Biochem, Fac Sci, Rua Campo Alegre 687, P-4169007 Porto, Portugal

[2] Univ Fernando Pessoa, Fac Ciencias Saude, Escola Super Saude, Praca 9 Abril,349, P-4249004 Porto, Portugal

[3] Univ Aberdeen, Dept Chem, Meston Bldg, Aberdeen AB24 3UE, Scotland

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2022年 / 58卷 / 01期

关键词：

2-aminobenzenethiol; 2-(1; 3-benzothiazol-2-yl)-4H-chromen-4-one; benzotriazol-1-yloxytripyrrolidinophosphonium hexa-fluorophosphate; chromene-2-carboxylic acid; spiro[1; 4-benzothiazine-2; 2; '-chromene]-3; 4; '(3; H; 4H)-dione; phosphorus oxychloride; acidic vs basic conditions; LEAD OPTIMIZATION; CHEMICAL ENTITIES; CHROMONE; DISCOVERY; SCAFFOLD;

D O I：

10.1007/s10593-022-03058-x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(1,3-Benzothiazol-2-yl)-4H-chromen-4-one and spiro[1,4-benzothiazine-2,2'-chromene]-3,4'(3'H,4H)-dione have been synthesized from 4-oxo-4H-chromene-2-carboxylic acid. The course of the reaction that usually occurs between the activated carboxylic acid and aromatic amines was changed upon the use of different reaction conditions (acidic or basic) and 2-aminobenzenethiol. As a result, new heterocyclic derivatives were obtained. Structures of the compounds have been established on the basis of spectral (1D and 2D NMR spectra) and X-ray data.

引用

页码：68 / 72

页数：5

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