Alternative methods for obtaining of cherylline derivatives

Stanimir Manolov

ISBN 10: 620207857X / ISBN 13: 9786202078573

Published by LAP LAMBERT Academic Publishing, 2017

About this Item

nach der Bestellung gedruckt Neuware - Printed after ordering - In this book are presented the results from research on alternative approaches towards the synthesis of 4- aryl-l,2,3,4-tetrhydroisoquinolines as synthetic analogues of the alkaloid cherylline. Optimal conditions for the synthesis of the required 2,2-disubstituted ethylamine precursors are found. The Schotten- Baumann method for amide synthesis is then successfully applied and the synthesized amides are used in an intramolecular -amidoalkylation reaction to obtain 4-substituted 1,2,3,4-tetrahydroisoquinolines. An eco-friendly procedure utilizing PPA/SiO2 catalyst for the intramolecular -amidoalkylation is developed. Microwave-assisted variant of this eco-friendly procedure is also successfully developed. By the Bischler-Napieralski method are synthesized five new 1,4- disubstituted-l,2,3,4-tetrahydroisoquinolines. These are potential inhibitors of DHODH. It is found that the reduction of 1,4-disubstituted 3,4-dihydroisoquinolines leads to formation of diastereoisomers. The diastereoisomers are successfully separated by preparative column chromatography and 2:1 (cis:trans) ratio is determined. This ratio is not affected by the temperature at which the reaction is carried out.

Seller Inventory # 9786202078573

Bibliographic Details

• Title: Alternative methods for obtaining of cherylline derivatives
• Publisher: LAP LAMBERT Academic Publishing
• Publication Date: 2017
• Language: English
• ISBN 10: 620207857X
• ISBN 13: 9786202078573
• Binding: Taschenbuch
• Condition: Neu
• Dimensions: 220W x 150H x 4D millimeters 220 millimeters width by 150 millimeters height by 4 millimeters depth
• Weight: 96 grams

About this title

Synopsis

In this book are presented the results from research on alternative approaches towards the synthesis of 4- aryl-l,2,3,4-tetrhydroisoquinolines as synthetic analogues of the alkaloid cherylline. Optimal conditions for the synthesis of the required 2,2-disubstituted ethylamine precursors are found. The Schotten- Baumann method for amide synthesis is then successfully applied and the synthesized amides are used in an intramolecular α-amidoalkylation reaction to obtain 4-substituted 1,2,3,4-tetrahydroisoquinolines. An eco-friendly procedure utilizing PPA/SiO2 catalyst for the intramolecular α -amidoalkylation is developed. Microwave-assisted variant of this eco-friendly procedure is also successfully developed. By the Bischler-Napieralski method are synthesized five new 1,4- disubstituted-l,2,3,4-tetrahydroisoquinolines. These are potential inhibitors of DHODH. It is found that the reduction of 1,4-disubstituted 3,4-dihydroisoquinolines leads to formation of diastereoisomers. The diastereoisomers are successfully separated by preparative column chromatography and 2:1 (cis:trans) ratio is determined. This ratio is not affected by the temperature at which the reaction is carried out.

About the Author

Stanimir Manolov received his B.Sc. of Computer chemistry (2008), M.Sc. (2009), and Ph.D. of Organic chemistry (2015) degrees from University of Plovdiv (Bulgaria). His research in the group of Prof. Iliyan Ivanov is focused on the development of new synthetic methodologies of biologically active natural compounds.