Regioselective C-H sulfenylation ofN-sulfonyl protected 7-azaindoles promoted by TBAI: a rapid synthesis of 3-thio-7-azaindoles

Hu Jingyan; Ji Xiaoming; Hao Shuai; Zhao Mingqin; Lai Miao; Ren Tianbao; Xi Gaolei; Wang Erbin; Wang Juanjuan; Wu Zhiyong

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Regioselective C-H sulfenylation ofN-sulfonyl protected 7-azaindoles promoted by TBAI: a rapid synthesis of 3-thio-7-azaindoles

机译：由TBAI促进的苏磺酰基的区域选择性C-H磺酰化促进的7-唑烷：3-Thio-7-氮杂合的快速合成

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This paper describes the regioselective C-3 sulfenylation ofN-sulfonyl protected 7-azaindoles with sulfonyl chlorides. In this transformation, dual roles of TBAI serving as both promoter and desulfonylation reagent have been demonstrated. The reaction proceeded smoothly under simple conditions to afford 3-thio-7-azaindoles in moderate to good yields with broad substrate scopes. This protocol refrains from using transition-metal catalysts, strong oxidants or bases, and shows its practical synthetic value in organic synthesis.

机译：本文描述了用磺酰氯保护的7-氮杂硅酸磺酰基的区域选择性C-3磺酰化。在该转化中，已经证明了作为启动子和脱硫试剂的TBai的双重作用。反应在简单的条件下平稳地进行，以提供3-硫代-7-氮杂硅，中等至良好的底物范围。该方案抑制了使用过渡金属催化剂，强氧化剂或碱，并显示出其有机合成中的实际合成值。

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《RSC Advances》 |2020年第53期|共5页
作者
Hu Jingyan; Ji Xiaoming; Hao Shuai; Zhao Mingqin; Lai Miao; Ren Tianbao; Xi Gaolei; Wang Erbin; Wang Juanjuan; Wu Zhiyong;
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作者单位

Henan Agr Univ Coll Tobacco Sci Flavors &

Fragrance Engn &

Technol Res Ctr Henan Zhengzhou 450002 Peoples R China;

Henan Agr Univ Coll Tobacco Sci Flavors &

Fragrance Engn &

Technol Res Ctr Henan Zhengzhou 450002 Peoples R China;

Henan Agr Univ Coll Tobacco Sci Flavors &

Fragrance Engn &

Technol Res Ctr Henan Zhengzhou 450002 Peoples R China;

Henan Agr Univ Coll Tobacco Sci Flavors &

Fragrance Engn &

Technol Res Ctr Henan Zhengzhou 450002 Peoples R China;

Henan Agr Univ Coll Tobacco Sci Flavors &

Fragrance Engn &

Technol Res Ctr Henan Zhengzhou 450002 Peoples R China;

Henan Agr Univ Coll Tobacco Sci Flavors &

Fragrance Engn &

Technol Res Ctr Henan Zhengzhou 450002 Peoples R China;

China Tobacco Henan Ind Co Ltd Technol Ctr Zhengzhou 450000 Henan Peoples R China;

China Tobacco Henan Ind Co Ltd Technol Ctr Zhengzhou 450000 Henan Peoples R China;

China Tobacco Henan Ind Co Ltd Technol Ctr Zhengzhou 450000 Henan Peoples R China;

Henan Agr Univ Coll Tobacco Sci Flavors &

Fragrance Engn &

Technol Res Ctr Henan Zhengzhou 450002 Peoples R China;

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中图分类化学;
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1. Regioselective C-H sulfenylation ofN-sulfonyl protected 7-azaindoles promoted by TBAI: a rapid synthesis of 3-thio-7-azaindoles [J] . Hu Jingyan, Ji Xiaoming, Hao Shuai, RSC Advances . 2020,第53期

机译：由TBAI促进的苏磺酰基的区域选择性C-H磺酰化促进的7-唑烷：3-Thio-7-氮杂合的快速合成
2. TBAI-mediated regioselective sulfenylation of indoles with sulfonyl chlorides in one pot [J] . He Yongzhao, Jiang Jun, Bao Wenhu, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2017,第49期

机译：TBAI介导的吲哚吲哚的区域选择性亚砜在一个罐中用磺酰氯
3. Synthesis of a new series of Ni(II), Cu(II), Co(II) and Pd(II) complexes with an ONS donor Schiff base: crystal structure, DFT study and catalytic investigation of palladium and nickel complexes towards deacylative sulfenylation of active methylenes and regioselective 3-sulfenylation of indoles via thiouronium salt formation [J] . Devi Namita, Sarma Kuladip, Rahaman Rajjakfur, Dalton transactions: An international journal of inorganic chemistry . 2018,第13期

机译：合成新系列Ni（II），Cu（II），Co（II）和Pd（II）配合物，具有ONS供体Schiff基地：晶体结构，DFT研究和钯和镍络合物朝向脱酰硫烯基化的催化研究通过硫代铵盐形成活性甲基和吲哚的吲哚的区域选择性3-磺酰化
4. Enzyme-Catalyzed Oligopeptide Synthesis: Rapid Regioselective Oligomerization of L-Glutamic Acid Diethyl Ester Catalyzed by Papain [C] . Symposium on polymer biocatalysis and biomaterials II . 2008

机译：酶催化的寡肽合成：瓜素催化L-谷氨酸二乙基酯的快速区域选择性寡聚化
5. The synthesis of a regioselectively protected staurosporine aglycone. [D] . Nomak, Rana. 2002

机译：区域选择性保护的星形孢菌素糖苷配基的合成。
6. Copper-Promoted Sulfenylation of sp2 C-H Bonds [O] . Ly Dieu Tran, Ilya Popov, Olafs Daugulis -1

机译：铜催化亚磺酰sp2 C-H债券
7. Regioselective C–H sulfenylation of N-sulfonyl protected 7-azaindoles promoted by TBAI: a rapid synthesis of 3-thio-7-azaindoles [O] . Jingyan Hu, Xiaoming Ji, Shuai Hao, 2020

机译：由TBAI促进的N-磺酰基的N-磺酰基的区域选择性C-H亚苯基化：3-Thio-7-氮杂胆量的快速合成

Regioselective C-H sulfenylation ofN-sulfonyl protected 7-azaindoles promoted by TBAI: a rapid synthesis of 3-thio-7-azaindoles

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