Solvent-dependent regio- and stereo-selective reactions of 3-formylchromones with 2-aminobenzothiazoles and transacetalization efficiency of the product 3-((benzo[d]thiazol-2-ylimino)butyl)-4H-chromen-4-one

Ahmed Owais; Cherkadu Vandana; Kalavagunta Praveen Kumar; Shang Jing

首页> 外文期刊>RSC Advances >Solvent-dependent regio- and stereo-selective reactions of 3-formylchromones with 2-aminobenzothiazoles and transacetalization efficiency of the product 3-((benzo[d]thiazol-2-ylimino)butyl)-4H-chromen-4-one

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Solvent-dependent regio- and stereo-selective reactions of 3-formylchromones with 2-aminobenzothiazoles and transacetalization efficiency of the product 3-((benzo[d]thiazol-2-ylimino)butyl)-4H-chromen-4-one

机译：3-甲酰基溴酮的溶剂依赖性测定和立体选择性反应，具有2-氨基苯并噻唑和产物3-（（苯并[D]噻唑-2-基咪嗪）丁基）-4H-铬-4-一

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Using 2-propanol as the solvent, 3-formylchromones and 2-aminobenzothiaoles formed corresponding imines, while 1 degrees and 2 degrees-alcohols formed the corresponding 2-alkoxy-3-enamines with selectivity for the Z-isomer. Changing the substrates with similar molecules such as 3-formylchromone with quinoline-, quinolone- and indole-3-carbaldehydes sometimes resulted in the formation of the corresponding imines, whereas replacing 2-aminobenzothiazole with amides resulted in the formation of acetals. Considering the effect of the solvent, replacing alcohols with the aprotic solvents THF and CH2Cl2 resulted in the formation of imines and enamines, which are the characteristic reactions of 2-propanol and other 1 degrees and 2 degrees-alcohols, respectively. 2-Alkoxy-3-enamines were found to undergo transacetalization with both short and long chain alcohols. The novelty of these reactions is that they did not require an external catalyst, all the reactions were performed at the same temperature, and purification was achieved by filtration. The transacetalization we performed herein is a new concept, which has not been reported to date. In contrast, other similar reactions, such as transalkoxylation, transalkylation, and transetherification, are performed on a commercial scale using expensive catalysts such as Otera's catalyst. The highly sensitive nature of 3-formylchromones towards variations in the substrates and solvents to form different products and the reason behind the selective formation of the Z-isomer of 2-alkoxy-3-enamines and its transacetalization efficiency need further studies to understand the reaction mechanism and possibly other factors such as solvent effects.

机译：使用2-丙醇作为溶剂，3-甲酰基溴酮和2-氨基苯基噻体形成相应的亚胺，而1度和2度醇形成相应的2-烷氧基-3-烯胺，具有Z-异构体的选择性。用喹啉 - ，喹诺酮和吲哚-3-碳醛（喹啉酮）改变诸如3-甲酰基溴酮等类似分子的底物有时会形成相应的亚胺，而用酰胺替换2-氨基苯并噻唑导致形成缩醛。考虑到溶剂的作用，用非质子溶剂THF和CH 2 Cl 2替换醇导致亚胺和烯胺的形成，它们分别是2-丙醇和其他1度和2度醇的特征反应。发现2-烷氧基-3-烯胺与短链和长链醇进行晶体化。这些反应的新颖性是它们不需要外部催化剂，所有反应在相同的温度下进行，并通过过滤实现纯化。我们在此进行的跨缩醛化是一种新的概念，尚未报告迄今为止。相反，使用昂贵的催化剂如Otera的催化剂，在商业规模上进行其他类似反应，例如废氧化物，烷基化和跨越酮化合物。 3-甲酰基溴酮朝向底物和溶剂的变化的高敏感性，形成不同产品的原因以及2-烷氧基-3-烯胺的Z-异构体的选择性形成及其横向化效率，需要进一步研究以了解反应机制和可能的其他因素，如溶剂效应。

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《RSC Advances》 |2019年第36期|共9页
作者
Ahmed Owais; Cherkadu Vandana; Kalavagunta Praveen Kumar; Shang Jing;
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作者单位

China Pharmaceut Univ Sch Life Sci &

Technol Nanjing 211198 Jiangsu Peoples R China;

CJEX Biochem R&

D Ctr 7&

8 2nd Cross Muniswamappa Layout Hosur Rd Bangalore 560068 Karnataka India;

China Pharmaceut Univ Sch Tradit Chinese Pharm Jiangsu Key Lab TCM Evaluat &

Translat Res State Key Lab Nat Med Nanjing 211198 Jiangsu Peoples R China;

China Pharmaceut Univ Sch Tradit Chinese Pharm Jiangsu Key Lab TCM Evaluat &

Translat Res State Key Lab Nat Med Nanjing 211198 Jiangsu Peoples R China;

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中图分类化学;
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1. Solvent-dependent regio- and stereo-selective reactions of 3-formylchromones with 2-aminobenzothiazoles and transacetalization efficiency of the product 3-((benzo[d]thiazol-2-ylimino)butyl)-4H-chromen-4-one [J] . Ahmed Owais, Cherkadu Vandana, Kalavagunta Praveen Kumar, RSC Advances . 2019,第36期

机译：3-甲酰基溴酮的溶剂依赖性测定和立体选择性反应，具有2-氨基苯并噻唑和产物3-（（苯并[D]噻唑-2-基咪嗪）丁基）-4H-铬-4-一
2. Solvent-dependent regio- and stereo-selective reactions of 3-formylchromones with 2-aminobenzothiazoles and transacetalization efficiency of the product 3-((benzo[d]thiazol-2-ylimino)butyl)-4H-chromen-4-one [J] . Owais Ahmed, Vandana Cherkadu, Praveen Kumar Kalavagunta, RSC Advances . 2019,第36期

机译：3-甲酰基色酮与2-氨基苯并噻唑的溶剂依赖性区域和立体选择性反应以及产物3-（（（苯并[d]噻唑-2-ylimino）丁基）-4H-chromen-4-one
3. Solvent-dependent regio- and stereo-selective reactions of 3-formylchromones with 2-aminobenzothiazoles and transacetalization efficiency of the product 3-((benzo[d]thiazol-2-ylimino)butyl)-4H-chromen-4-one [J] . Owais Ahmed, Vandana Cherkadu, Praveen Kumar Kalavagunta, RSC Advances . 2019,第36期

机译：3-甲酰基色酮与2-氨基苯并噻唑的溶剂依赖性区域和立体选择性反应以及产物3-（（（苯并[d]噻唑-2-ylimino）丁基）-4H-chromen-4-one
4. Solvent-dependent regio- and stereo-selective reactions of 3-formylchromones with 2-aminobenzothiazoles and transacetalization efficiency of the product 3-((benzodthiazol-2-ylimino)butyl)-4H-chromen-4-one [O] . Owais Ahmed, Vandana Cherkadu, Praveen Kumar Kalavagunta, 2019

机译：3-甲酰基溴酮的溶剂依赖性测定和立体选择性反应，具有2-氨基苯并噻唑和产物3-（（苯并D噻唑-2-基咪嗪）丁基）-4H-铬-4-一

Solvent-dependent regio- and stereo-selective reactions of 3-formylchromones with 2-aminobenzothiazoles and transacetalization efficiency of the product 3-((benzo[d]thiazol-2-ylimino)butyl)-4H-chromen-4-one

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