Efficient synthesis of novel cyclic fused-phenothiazines via domino cyclization of 2-(benzo[b][1,4]thiazin-3-ylidene)acetate, aromatic aldehydes and cyclic 1,3-diketones†,Organic Chemistry Frontiers

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Efficient synthesis of novel cyclic fused-phenothiazines via domino cyclization of 2-(benzo[b][1,4]thiazin-3-ylidene)acetate, aromatic aldehydes and cyclic 1,3-diketones†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2019-08-30 , DOI: 10.1039/c9qo00951e
Jing Sun _{1,

2,

3,

4} , Quan-Shun Sun _{1,

2,

3,

4} , Chao-Guo Yan _{1,

2,

3,

4}

Affiliation

Functionalized 2,3,4,7-tetrahydrobenzo[c]phenothiazines and 7,9,10,12-tetrahydrobenzo[b]phenothiazines were selectively synthesized from a three-component reaction of aromatic aldehydes, cyclic 1,3-diketones and methyl 2-(benzo[b][1,4]thiazin-3-ylidene)acetate in refluxing AcOH/CH₃CN medium or in refluxing acetic acid. On the other hand, the domino cyclization reaction of aromatic aldehydes with methyl 2-(benzo[b][1,4]thiazin-3-ylidene)acetate in AcOH/CH₃CN medium resulted in polycyclic 8,14-methanobenzo[2,3][1,4]thiazocino[6,7-a]phenothiazines in satisfactory yields. Additionally, similar reactions with some typical 1,2-dicarbonyl compounds afforded diverse polycyclic compounds.

中文翻译：

新型环状稠吩噻嗪的有效合成通过2-（苯并[多米诺环化b ] [1,4]噻嗪-3-亚基）乙酸乙酯，芳香醛和环状1,3-二酮†

从芳族醛，环状1,3-二酮和甲基2的三组分反应中选择性合成功能化的2,3,4,7-四氢苯并[ c ]吩噻嗪和7,9,10,12-四氢苯并[ b ]吩噻嗪在回流的AcOH / CH ₃ CN介质中或在回流的乙酸中生成-（苯并[ b ] [1,4]噻嗪-3-亚丙基）乙酸酯。另一方面，芳香醛与2-（苯并[ b ] [1,4]噻嗪-3-亚烷基）乙酸甲酯在AcOH / CH ₃ CN介质中的多米诺环化反应生成多环8,14-甲氧基苯并[2] ，3] [1,4] thiazocino [6,7- a]吩噻嗪，收率令人满意。另外，与一些典型的1,2-二羰基化合物的类似反应提供了多种多环化合物。

更新日期：2019-10-10

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