731-51-1Relevant academic research and scientific papers
One-step conversion of 2-Amino- N ′-arylbenzamidines into 3-aryl-4-imino-3,4-dihydroquinazoline-2-carbonitriles using 4,5-dichloro-1,2,3- dithiazolium chloride
Mirallai, Styliana I.,Manos, Manolis J.,Koutentis, Panayiotis A.
, p. 9906 - 9913 (2013/10/22)
2-Amino-N′-arylbenzamidines react with 4,5-dichloro-1,2,3- dithiazolium chloride (Appel salt) in the presence of Huenig's base (2 equiv) to give in one step 3-aryl-4-imino-3,4-dihydroquinazoline-2-carbonitriles in 53-81% yields. Nine examples are presented along with the single-crystal X-ray structure of 4-imino-3-phenyl-3,4-dihydroquinazoline-2-carbonitrile. Furthermore, the behavior of the latter toward both acid and base hydrolysis is investigated. All new compounds are fully characterized, and a mechanistic rationale for the formation of the iminoquinazolines is provided.
ortho-Lithiophenyl isocyanide: A versatile precursor for 3H-quinazolin-4-ones and 3H-quinazolin-4-thiones
Lygin, Alexander V.,De Meijere, Armin
supporting information; experimental part, p. 389 - 392 (2009/09/05)
(Chemical Equation Presented) ortho-Lithiophenyl isocyanide has been generated from ortho-bromophenyl isocyanide and successfully employed toward the synthesis of 2-substituted phenyl Isocyanides as well as 2,3-disubstituted 3H-quinazoline-4-ones and 3H-q
Reactions of Isocyanates with Methyl N-(Cyanothioformyl)anthranilate
Deck,Papadopoulos,Smith
, p. 885 - 893 (2007/10/03)
The triethylamine-catalyzed reactions of methyl N-(cyanothioformyl)anthranilate (1) with isocyanates result in cyclization involving the cyano group to form methyl 2-(4-imino-2-oxo-3-substituted-5-thioxoimidazolidin-1-yl)benzoates (4). Ring closure at the ester carbonyl to form 3-aryl-3,4-dihydro-4-oxoquinazoline-2-carbonitriles (8) is observed when the S-methyl derivative of 1 is allowed to react with aromatic amines.
