67461-76-1

Usage

InChI:InChI=1/C14H11N3O/c15-13-11-8-4-5-9-12(11)16-14(18)17(13)10-6-2-1-3-7-10/h1-9H,15H2

Upstream product

• 13114-96-0 N-phenyl-N'-(2-cyanophenyl)carbamide 
• 92165-07-6 N-(2-cyanophenyl)-N'-phenylthiourea 
• 951-48-4 2-amino-N′-phenylbenzamidine 

Downstream Products

• 603-23-6 3-phenyl-2,4-(1H,3H)-quinazolinedione 

Relevant 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

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.

Synthesis and X-ray characterisation of a new polycondensed heterocycle obtained by a novel Mn(III)-mediated cascade reaction of 2-cyanophenyl isothiocyanate

2-Cyanophenyl isothiocyanate reacted with Mn(III) acetate in acetic acid or acetonitrile to give fair yields of a new polycondensed heterocycle arising from the joining together of two molecules of the starting isothiocyanate with loss of a CS moiety. The yields were close to 90% when the reaction was carried out in the presence of diethyl malonate. This compound was unambiguously identified by X-ray crystallography. Under the same conditions, 2-(methoxycarbonyl)phenyl isothiocyanate gave a quinazolinimine derivative instead which is likely to arise from cyclisation of an intermediate N,N′-diarylthiourea. The mechanism of formation of the former compound probably involves formation of a N,N′-bis(2-cyanophenyl)thiourea, followed by rearrangement and radical tandem ring closure of the corresponding cyclic imine derivative. This hypothesis is also supported by semiempirical calculations.