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