Fused azole-thiazolines via one-pot cyclization of functionalized N-heterocyclic carbene precursors,Organic & Biomolecular Chemistry

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Fused azole-thiazolines via one-pot cyclization of functionalized N-heterocyclic carbene precursors
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020/03/10 , DOI: 10.1039/c9ob02548k
Qiaoqiao Teng _{1,

2,

3,

4} , Chandan Singh _{1,

2,

3,

4} , Yuan Han _{1,

2,

3,

4} , Han Vinh Huynh _{1,

2,

3,

4}

Affiliation

A one-pot two-step methodology was exploited to synthesize fused thiazoline-azolium salts via reactions of bromoalkyl-azolium salts with KSCN and NaOH. The synthetic feasibility and versatility was demonstrated by the high yield (>80%) preparation of 13 salts with different backbones, linkers and substituents. Using methylpropionato as an N-protecting group, the resulting salts could be further derivatized to their neutral azole-thiazolines. The reaction sequence proceeds via (i) Br → SCN substitution, (ii) N-heterocyclic carbene formation, (iii) carbene attack of the S atom and CN⁻ displacement in the alkyl−S−C [triple bond, length as m-dash]

N unit, and (iv) methyl acrylate elimination.

中文翻译：

通过一锅环化功能化的N-杂环卡宾前体进行熔融的吡唑并噻唑啉

利用一锅两步法通过溴代烷基偶氮盐与KSCN和NaOH的反应合成稠合的噻唑啉-偶氮盐。高产率（> 80％）制备具有不同主链，连接基和取代基的13种盐证明了合成的可行性和多功能性。使用甲基丙酸酯作为N-保护基，可以将所得盐进一步衍生为它们的中性唑-噻唑啉。反应顺序进行通过（ⅰ）溴→SCN取代，（ⅱ）N-杂环卡宾的形成，（iii）所述S原子和CN的卡宾攻击^-在烷基-S-C位移 [三重键，长度为m-破折号]

N个单位，和（iv）甲基消除丙烯酸酯。

更新日期：2020-04-01

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