A versatile approach for the synthesis of 8H-thieno[2,3-b]indoles and N-[2-(2-N-(R1,R2)-2-Thioxoacetyl)-phenyl]acetamides from 1-acetyl-1,2-dihydro-3H-indol-3-one (Acetylindoxyl) and its derivatives: A novel synthesis of intermediate (1-acetyl-1h-indol-3-yl)malononitrile/cyanoacetates

Velezheva V.S.; Lepyoshkin A.Y.; Turchin K.F.; Fedorova I.N.; Peregudov A.S.; Brennan P.J.

首页> 外文期刊>Journal of Heterocyclic Chemistry: The International Journal of Heterocyclic Chemistry >A versatile approach for the synthesis of 8H-thieno[2,3-b]indoles and N-[2-(2-N-(R1,R2)-2-Thioxoacetyl)-phenyl]acetamides from 1-acetyl-1,2-dihydro-3H-indol-3-one (Acetylindoxyl) and its derivatives: A novel synthesis of intermediate (1-acetyl-1h-indol-3-yl)malononitrile/cyanoacetates

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A versatile approach for the synthesis of 8H-thieno[2,3-b]indoles and N-[2-(2-N-(R1,R2)-2-Thioxoacetyl)-phenyl]acetamides from 1-acetyl-1,2-dihydro-3H-indol-3-one (Acetylindoxyl) and its derivatives: A novel synthesis of intermediate (1-acetyl-1h-indol-3-yl)malononitrile/cyanoacetates

机译：一种由1-乙酰基1合成8H-噻吩并[2,3-b]吲哚和N- [2-（2-N-（R1，R2）-2-硫代乙酰基）-苯基]乙酰胺的通用方法， 2-二氢-3H-吲哚-3-酮（乙酰吲哚基）及其衍生物：中间体（1-乙酰基-1h-吲哚-3-基）丙二腈/氰基乙酸酯的新型合成

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We report on two approaches for the synthesis of new 2-amino-3-cyano/ alkoxycarbonyl-8H-thieno[2,3-b]indoles and another one for the synthesis of 2-N,N-dialkylamino-3-cyano/aryl-8H-thieno[2,3-b]indoles, based either on acetylindoxyl and (1-acetyl-1H-indol-3-yl)malononitrile/cyanoacetates or 2-bromoacetylindoxyl transformations. A new, simple, rapid, and efficient method for the synthesis of valuable key intermediate malononitrile/cyanoacetates based on acetylindoxyl condensation with malononitrile or cyanoacetates in the presence of triethylamine has been developed. A number of synthetic procedures for the preparation of thioacetamides, 1-acetylthioisatin, and 2,2-disubstituted indoxyls have been elaborated during the synthesis of thieno[2,3-b]indoles. Thioacetamides have been shown as novel agents active against Mycobacterium tuberculosis H37Rv, the cause of tuberculosis, with minimal inhibitory concentration values ranging between 5 and 21 μg/mL.

机译：我们报告了两种合成新的2-氨基-3-氰基/烷氧基羰基-8H-噻吩并[2,3-b]吲哚的方法，另一种合成2-N，N-二烷基氨基-3-氰基/基于乙酰基吲哚基和（1-乙酰基-1H-吲哚-3-基）丙二腈/氰基乙酸酯或2-溴乙酰基吲哚基转化的芳基-8H-噻吩并[2,3-b]吲哚。已经开发了一种新的，简单，快速和有效的方法，用于在三乙胺存在下，基于乙酰吲哚基与丙二腈或氰基乙酸酯的缩合，合成有价值的关键中间体丙二腈/氰基乙酸酯。在噻吩并[2，3-b]吲哚的合成过程中，已经详细地制备了许多用于制备硫代乙酰胺，1-乙酰基硫代靛红和2，2-二取代的吲哚酚的合成方法。硫代乙酰胺已被证明是对结核分枝杆菌H37Rv有活性的新型药物，其抑制浓度范围在5至21μg/ mL之间。

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《Journal of Heterocyclic Chemistry: The International Journal of Heterocyclic Chemistry》 |2013年第2期|共12页
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Velezheva V.S.; Lepyoshkin A.Y.; Turchin K.F.; Fedorova I.N.; Peregudov A.S.; Brennan P.J.;
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1. A versatile approach for the synthesis of 8H-thieno[2,3-b]indoles and N-[2-(2-N-(R1,R2)-2-Thioxoacetyl)-phenyl]acetamides from 1-acetyl-1,2-dihydro-3H-indol-3-one (Acetylindoxyl) and its derivatives: A novel synthesis of intermediate (1-acetyl-1h-indol-3-yl)malononitrile/cyanoacetates [J] . Velezheva V.S., Lepyoshkin A.Y., Turchin K.F., Journal of Heterocyclic Chemistry: The International Journal of Heterocyclic Chemistry . 2013,第2期

机译：一种由1-乙酰基1合成8H-噻吩并[2,3-b]吲哚和N- [2-（2-N-（R1，R2）-2-硫代乙酰基）-苯基]乙酰胺的通用方法， 2-二氢-3H-吲哚-3-酮（乙酰吲哚基）及其衍生物：中间体（1-乙酰基-1h-吲哚-3-基）丙二腈/氰基乙酸酯的新型合成
2. Microwave-assisted synthesis, structural elucidation and biological assessment of 2-(2-acetamidophenyl)-2-oxo-N phenyl acetamide and N-(2-(2-oxo-2(phenylamino)acetyl)phenyl)propionamide derivatives [J] . Ghazzali M., El-Faham A., Abdel-Megeed A., Journal of Molecular Structure . 2012,第Null期

机译：2-（2-乙酰氨基苯基）-2-氧代-N苯基乙酰胺和N-（2-（2-氧代-2（苯基氨基）乙酰基）苯基）丙酰胺衍生物的微波辅助合成，结构解析和生物学评估
3. Fluorinated N-[2-(haloalkyl)phenyl]imidoyl chloride, a key intermediate for the synthesis of 2-fluoroalkyl substituted indole derivatives via Grignard cyclization process [J] . Zengxue Wang, Fenglian Ge, Wen Wan Journal of Fluorine Chemistry . 2007,第10期

机译：氟化N- [2-（卤代烷基）苯基]亚氨基氯，通过格氏环化法合成2-氟烷基取代的吲哚衍生物的关键中间体
4. Synthesis Spectroscopic Identification and Molecular Docking of Certain N-(2-{2-(1H-Indol-2-ylcarbonyl) hydrazinyl(oxo)acetyl}phenyl)acetamides and N-2-(2-{2-(Acetylamino)phenyl(oxo)acetyl}hydrazinyl)-2-oxoethyl-1H-indole-2-carboxamides: New Antimicrobial Agents [O] . Maha S. Almutairi, Azza S. Zakaria, Reem I. Al-Wabli, 2018

机译：某些N-（2-{2-（1H-吲哚-2-基羰基）肼基（氧代）乙酰基}苯基}乙酰胺和N- 2-（2-{2-的合成光谱鉴定和分子对接（乙酰氨基）苯基（氧代）乙酰基}肼基）-2-氧代乙基 -1H-吲哚-2-羧酰胺：新的抗菌剂
5. Synthesis and evaluation of [N-(Substituted phenyl)-2-(3-substituted) sulfamoyl) phenyl)] acetamide derivatives as anticancer agents [O] . Chandrakant D. Pawar, Aniket P. Sarkate, Kshipra S. Karnik, 2017

机译：[N-（取代苯基）-2-（3-取代）氨磺酰基）苯基）]乙酰胺衍生物作为抗癌剂的合成与评价

A versatile approach for the synthesis of 8H-thieno[2,3-b]indoles and N-[2-(2-N-(R1,R2)-2-Thioxoacetyl)-phenyl]acetamides from 1-acetyl-1,2-dihydro-3H-indol-3-one (Acetylindoxyl) and its derivatives: A novel synthesis of intermediate (1-acetyl-1h-indol-3-yl)malononitrile/cyanoacetates

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