One-Pot Synthesis of C<inf>2</inf>Symmetric and Asymmetric N,N′,N″-Substituted Guanidines from Aryl Isothiocyanates and Amines

One-Pot Synthesis of C<inf>2</inf>Symmetric and Asymmetric N,N′,N″-Substituted Guanidines from Aryl Isothiocyanates and Amines

© Georg Thieme Verlag. Highly substituted guanidines were conveniently prepared through a one-pot reaction between aryl isothiocyanates and amines mediated by the Ph3P-I2/Et3N system. The C2-symmetric N,N′,N″-substituted guanidines were readily accessed using a 1:2 molar ratio of an aryl isothiocyan...

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Main Authors: Sirilak Wangngae, Mookda Pattarawarapan, Wong Phakhodee
Format: Journal
Published: 2018
Subjects:
Chemistry
Online Access:https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84953410328&origin=inward
http://cmuir.cmu.ac.th/jspui/handle/6653943832/55473
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Institution: Chiang Mai University
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spelling th-cmuir.6653943832-554732018-09-05T02:56:38Z One-Pot Synthesis of C<inf>2</inf>Symmetric and Asymmetric N,N′,N″-Substituted Guanidines from Aryl Isothiocyanates and Amines Sirilak Wangngae Mookda Pattarawarapan Wong Phakhodee Chemistry © Georg Thieme Verlag. Highly substituted guanidines were conveniently prepared through a one-pot reaction between aryl isothiocyanates and amines mediated by the Ph3P-I2/Et3N system. The C2-symmetric N,N′,N″-substituted guanidines were readily accessed using a 1:2 molar ratio of an aryl isothiocyanate and an amine; while sequential addition of two different amines in equimolar ratios gave rise to asymmetric derivatives. Both primary and secondary amines were found to react preferentially with electron-deficient aryl isothiocyanates, rapidly providing guanidines in good yields under mild conditions. 2018-09-05T02:56:38Z 2018-09-05T02:56:38Z 2016-01-05 Journal 14372096 09365214 2-s2.0-84953410328 10.1055/s-0035-1561201 https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84953410328&origin=inward http://cmuir.cmu.ac.th/jspui/handle/6653943832/55473
institution Chiang Mai University
building Chiang Mai University Library
country Thailand
collection CMU Intellectual Repository
topic Chemistry
spellingShingle Chemistry
Sirilak Wangngae
Mookda Pattarawarapan
Wong Phakhodee
One-Pot Synthesis of C<inf>2</inf>Symmetric and Asymmetric N,N′,N″-Substituted Guanidines from Aryl Isothiocyanates and Amines
description © Georg Thieme Verlag. Highly substituted guanidines were conveniently prepared through a one-pot reaction between aryl isothiocyanates and amines mediated by the Ph3P-I2/Et3N system. The C2-symmetric N,N′,N″-substituted guanidines were readily accessed using a 1:2 molar ratio of an aryl isothiocyanate and an amine; while sequential addition of two different amines in equimolar ratios gave rise to asymmetric derivatives. Both primary and secondary amines were found to react preferentially with electron-deficient aryl isothiocyanates, rapidly providing guanidines in good yields under mild conditions.
format Journal
author Sirilak Wangngae
Mookda Pattarawarapan
Wong Phakhodee
author_facet Sirilak Wangngae
Mookda Pattarawarapan
Wong Phakhodee
author_sort Sirilak Wangngae
title One-Pot Synthesis of C<inf>2</inf>Symmetric and Asymmetric N,N′,N″-Substituted Guanidines from Aryl Isothiocyanates and Amines
title_short One-Pot Synthesis of C<inf>2</inf>Symmetric and Asymmetric N,N′,N″-Substituted Guanidines from Aryl Isothiocyanates and Amines
title_full One-Pot Synthesis of C<inf>2</inf>Symmetric and Asymmetric N,N′,N″-Substituted Guanidines from Aryl Isothiocyanates and Amines
title_fullStr One-Pot Synthesis of C<inf>2</inf>Symmetric and Asymmetric N,N′,N″-Substituted Guanidines from Aryl Isothiocyanates and Amines
title_full_unstemmed One-Pot Synthesis of C<inf>2</inf>Symmetric and Asymmetric N,N′,N″-Substituted Guanidines from Aryl Isothiocyanates and Amines
title_sort one-pot synthesis of c<inf>2</inf>symmetric and asymmetric n,n′,n″-substituted guanidines from aryl isothiocyanates and amines
publishDate 2018
url https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84953410328&origin=inward
http://cmuir.cmu.ac.th/jspui/handle/6653943832/55473
_version_ 1681424512283836416

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