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3-(2,4-二氧代环己基)丙酸乙酯作为一种新型前体用于合成N-取代的4,4a,5,6-四氢喹啉-2,7(1H,3H)-二酮及其相应的3,4-二氢-7-羟基喹啉-2(1H)-酮和7-羟基喹啉-2(1H)-酮

Ethyl 3-(2,4-dioxocyclohexyl)propanoate as a novel precursor for N-substituted 4,4a,5,6-tetrahydroquinoline-2,7(1H,3H)-diones and their corresponding 3,4-dihydro-7-hydroxyquinolin-2(1H)-ones and 7-hydroxyquinolin-2(1H)-ones synthesis.

作者信息

Thakur Vandna, Sharma Dharminder, Das Pralay

机构信息

Natural Product Chemistry and Process Development, CSIR-Institute of Himalayan Bioresource Technology, Palampur, H.P., 176061, India.

Academy of Scientific & Innovative Research, New Delhi, India.

出版信息

Mol Divers. 2016 Feb;20(1):29-40. doi: 10.1007/s11030-015-9643-x. Epub 2015 Nov 4.

DOI:10.1007/s11030-015-9643-x
PMID:26537729
Abstract

Ethyl 3-(2,4-dioxocyclohexyl)propanoate has been explored as a precursor for the synthesis of N-substituted 4,4a,5,6-tetrahydroquinoline-2,7(1H,3H)-diones following conventional protecvtion, selective amidation, and deprotective-cyclization approaches. Moreover, a facile process for the selective dehydrogenative aromatization of these diones was developed to afford the corresponding N-substituted 3,4-dihydro-7-hydroxyquinolin-2(1H)-ones and N-substituted 7-hydroxyquinolin-2(1H)-ones under mild conditions.

摘要

3-(2,4-二氧代环己基)丙酸乙酯已被研究作为一种前体，用于通过传统的保护、选择性酰胺化和去保护环化方法合成N-取代的4,4a,5,6-四氢喹啉-2,7(1H,3H)-二酮。此外，还开发了一种简便的方法，用于这些二酮的选择性脱氢芳构化，以便在温和条件下得到相应的N-取代的3,4-二氢-7-羟基喹啉-2(1H)-酮和N-取代的7-羟基喹啉-2(1H)-酮。

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