J 2017

Convenient domino synthesis of quinazolin-4(3H)-ylidene carbothioamides and carbamothioates

FATHALLA, Walid Mohamed and Pavel PAZDERA

Basic information

Original name

Convenient domino synthesis of quinazolin-4(3H)-ylidene carbothioamides and carbamothioates

Authors

FATHALLA, Walid Mohamed (818 Egypt) and Pavel PAZDERA (203 Czech Republic, guarantor, belonging to the institution)

Edition

Tetrahedron, Oxford, ERGAMON-ELSEVIER SCIENCE LTD, 2017, 0040-4020

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

Netherlands

Confidentiality degree

není předmětem státního či obchodního tajemství

Impact factor

Impact factor: 2.377

RIV identification code

RIV/00216224:14310/17:00097013

Organization unit

Faculty of Science

DOI

UT WoS

000405977600010

Keywords in English

imidoyl isothiocyanate; quinazolin-4(3H)-ylidene carbothioamides; quinazolin-4(3H)-ylidene carbamothioate; Cascade reaction; imidoyl chloride; Dimroth rearrangement; intramolecular hydrogen bond.

Tags

Změněno: 30/3/2018 20:09, Ing. Nicole Zrilić

Abstract

V originále

A simple convenient protocol for the synthesis of secondary amine N-(2- (substitutedphenyl)quinazolin-4(3H)-ylidene) carbothioamides and O-alkyl N-2- (substitutedphenyl)quinazolin-4(3H)-ylidene carbamothioates has been described. It involves the cascade reaction of various secondary amines or alcohols with imidoylisothiocyanates in acetonitrile to afford the desired compounds in excellent yields. The reaction time was 48 h under reflux conditions, involved a simple work up, to form 42 examples of pure products in high yields. The precursor imidoyl isothiocyanates were prepared from the corresponding benzanilides and were purified by flash chromatography.