Synthesis of Glycoconjugate Benzothiazoles via Cleavage of Benzotriazole Ring

被引：55

作者：

Kumar, Dhananjay ^{[1
]}

Mishra, Amrita ^{[1
]}

Mishra, Bhuwan B. ^{[1
]}

Bhattacharya, Subrato ^{[1
]}

Tiwari, Vinod K. ^{[1
]}

机构：

[1] Banaras Hindu Univ, Dept Chem, Ctr Adv Study, Varanasi 221005, Uttar Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 03期

关键词：

ELECTRON-PARAMAGNETIC-RESONANCE; PALLADIUM-CATALYZED SYNTHESIS; N-SUBSTITUTED BENZOTRIAZOLES; S BOND FORMATION; CONVENIENT SYNTHESIS; ONE-POT; PARALLEL SYNTHESIS; FACILE SYNTHESIS; 2-ARYLBENZOTHIAZOLES; CYCLIZATION;

D O I：

10.1021/jo3021049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise and efficacious benzotriazole-mediated novel two-step protocol has been developed for easy access to glycoconjugate benzothiazoles from protected carbohydrates. The benzotriazolemethanethione 3, prepared by the reaction of free alcohol with bis(1H-benzo[1,2,3]triazol-1-yl)methanethione, on treatment with silanes or stannane under heating or microwave irradiation undergoes free radical beta-scission of N-N bond and affords diverse range of 2-O-substituted benzothiazoles 4 via cyclative elimination of molecular nitrogen. The structures of all of the compounds have been elucidated using JR. NMR, MS, and elemental analysis, and five of them have been characterized by single-crystal X-ray analysis.

引用

页码：899 / 909

页数：11

共 73 条

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