• 主题
高级搜索  >
历史搜索 清空历史
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
【24h】

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

获取原文
           
页面导航
  • 摘要
  • 著录项
  • 相似文献
  • 相关主题

摘要

Using 2-propanol as the solvent, 3-formylchromones and 2-aminobenzothiaoles formed corresponding imines, while 1° and 2°-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 CH _(2) Cl _(2) resulted in the formation of imines and enamines, which are the characteristic reactions of 2-propanol and other 1° and 2°-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：用2-丙醇作为溶剂，3-甲酰基色酮和2-氨基苯并噻吩形成相应的亚胺，而1°和2°-醇形成相应的对Z-异构体具有选择性的2-烷氧基-3-烯胺。用类似的分子（例如3-甲酰基色酮）与喹啉-，喹诺酮-和吲哚-3-甲醛一起改变底物有时会导致形成相应的亚胺，而用酰胺取代2-氨基苯并噻唑会导致缩醛的形成。考虑到溶剂的影响，用质子惰性溶剂THF和CH _（2）Cl _（2）代替醇导致亚胺和烯胺的形成，这是2-丙醇与其他1°和2°的特征反应-酒精。发现2-烷氧基-3-烯胺与短链和长链醇均发生缩醛化。这些反应的新颖之处在于它们不需要外部催化剂，所有反应均在相同温度下进行，并通过过滤进行纯化。我们在本文中进行的转缩醛化是一个新概念，迄今为止尚未报道。相反，其他类似的反应，例如转烷氧基化，烷基转移和醚化反应，则是使用昂贵的催化剂，例如Otera催化剂，以商业规模进行的。 3-甲酰基色酮对底物和溶剂变化以形成不同产物的高度敏感性，以及2-烷氧基-3-烯胺的Z-异构体选择性形成及其反缩醛化效率背后的原因需要进一步研究以了解反应机理和可能的其他因素，例如溶剂效应。

著录项

相似文献

  • 外文文献
  • 中文文献
  • 专利
获取原文

客服邮箱：kefu@zhangqiaokeyan.com

京公网安备：11010802029741号 ICP备案号：京ICP备15016152号-6 六维联合信息科技 (北京) 有限公司©版权所有

  • 客服微信

  • 服务号