Synlett ( IF 2 ) Pub Date : 2021-09-02 , DOI: 10.1055/s-0040-1719830 Peter Langer 1, 2
Domino reactions of heterocyclic enamines with chromone derivatives provides a convenient synthesis of a great variety of annulated heterocyclic ring systems. The course of the reaction depends on the type of substituent located at position 3 of the chromone. Reactions of 3-unsubstituted chromones, 3-nitrochromones, and 3-halochromones proceed by conjugate addition of the carbon atom of the enamine to carbon C-2 of the chromone, ring cleavage, and recyclization via the chromone carbonyl group. In the case of 3-formylchromes, 3-dichloroacetylchromone, 3-perfluoroalkanoylthiochromones, 3-(2-fluorobenzoyl)chromones, and 3-methoxalylchromones the final cyclization proceeds via the carbonyl group located outside the chromone moiety. The functional groups located at the carbonyl group at position 3 of the chromone allow for further synthetic transformations including additional ring closures.
Contents
1 Introduction
2 3-Unsubstituted Chromones
3 3-Nitrochromones
4 3-Formylchromes
5 3-Dichloroacetylchromone
6 3-Perfluoroalkanoylthiochromones
7 3-Methoxalylchromones
8 3-(2-Fluorobenzoyl)chromones
9 3-Halochromones
10 Chromone-3-carboxylic Acids
11 Conclusions
中文翻译:
色酮与杂环烯胺的多米诺反应
杂环烯胺与色酮衍生物的多米诺反应提供了多种环状杂环系统的方便合成。反应过程取决于位于色酮 3 位的取代基的类型。3-未取代的色酮、3-硝基色酮和 3-卤色酮的反应是通过将烯胺的碳原子与色酮的碳 C-2 共轭加成、开环和通过色酮羰基再环化来进行的。对于 3-甲酰基色酮、3-二氯乙酰色酮、3-全氟烷酰基硫色酮、3-(2-氟苯甲酰基)色酮和 3-甲氧色酮,最终环化通过位于色酮部分外的羰基进行。
内容
1 简介
2 3-未取代的染色体
3 3-硝基色酮
4 3-甲酰基色素
5 3-二氯乙酰色酮
6 3-全氟烷酰基硫色酮
7 3-甲草酰色酮
8 3-(2-氟苯甲酰基)色酮
9 3-卤色酮
10 色酮-3-羧酸
11 结论