TY - JOUR
T1 - 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
AU - Mirallai, Styliana I.
AU - Manos, Manolis J.
AU - Koutentis, Panayiotis A.
PY - 2013/10/4
Y1 - 2013/10/4
N2 - 2-Amino-N′-arylbenzamidines react with 4,5-dichloro-1,2,3- dithiazolium chloride (Appel salt) in the presence of Hünig'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.
AB - 2-Amino-N′-arylbenzamidines react with 4,5-dichloro-1,2,3- dithiazolium chloride (Appel salt) in the presence of Hünig'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.
UR - http://www.scopus.com/inward/record.url?scp=84885165580&partnerID=8YFLogxK
U2 - 10.1021/jo401648t
DO - 10.1021/jo401648t
M3 - Article
C2 - 24053152
AN - SCOPUS:84885165580
SN - 0022-3263
VL - 78
SP - 9906
EP - 9913
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -