Synthesis of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl) carbonylamino] alkanoates and methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1- phenylquinolin-3-yl)carbonyl-amino)alkanamido] alkanoate

FATHALA, Walid Mohamed and Pavel PAZDERA. Synthesis of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl) carbonylamino] alkanoates and methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1- phenylquinolin-3-yl)carbonyl-amino)alkanamido] alkanoate. ARKIVOC. GAINESVILLE, USA: ARCAT-USA, 2017, vol. 2017, No 4, p. 158-173. ISSN 1551-7004. Available from: https://dx.doi.org/10.3998/ark.5550190.p009.946.

Basic information

• Original name: Synthesis of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl) carbonylamino] alkanoates and methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1- phenylquinolin-3-yl)carbonyl-amino)alkanamido] alkanoate
• Authors: FATHALA, Walid Mohamed (818 Egypt) and Pavel PAZDERA (203 Czech Republic, guarantor, belonging to the institution).
• Edition: ARKIVOC, GAINESVILLE, USA, ARCAT-USA, 2017, 1551-7004.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10401 Organic chemistry
• Country of publisher: United States of America
• Confidentiality degree: is not subject to a state or trade secret
• WWW: URL
• Impact factor: Impact factor: 1.048
• RIV identification code: RIV/00216224:14310/17:00097589
• Organization unit: Faculty of Science
• Doi: http://dx.doi.org/10.3998/ark.5550190.p009.946
• UT WoS: 000414746900014
• Keywords in English: Amino acid esters; DCC coupling method; azide coupling method; direct amino acid condensation; anisotropy; intramolecular hydrogen bond interactions; linomide
• Tags: NZ, rivok
• Tags: International impact, Reviewed

Abstract

A series of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino] alkanoates 7a-f has been developed by the direct condensation of ethyl [4-hydroxy-2-oxo--1-phenyl-1,2-dihydro-3-quinoline] carboxylate 4 with amino acid ester hydrochloride in the presence of triethylamine. The quinoline amino acid esters 7a-f were the key intermediate for the preparation of a series of methyl 2-[2-((1,2-dihydro-4-hydroxy-2- oxo-1-phenylquinolin-3-yl)carbonylamino)alkanamido] alkanoate 10-13(a-f) via azide coupling method with amino acid ester.