TY - JOUR
T1 - One-pot synthesis of diethyl 4,4′-(1,4-phenylene)bis-[6-(halomethyl)- 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates] and their bispyrrolocyclization
AU - Lebedyeva, Iryna O.
AU - Povstyanoy, Mykhaylo V.
AU - Povstyanoy, Vyacheslav M.
AU - Panasyuk, Oleksandr G.
AU - Guban', Evgen S.
AU - Ryabitskii, Aleksey B.
PY - 2010/9
Y1 - 2010/9
N2 - A one-pot synthesis of diethyl 4,4′-(1,4-phenylene)bis[6- (chloromethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates] is proposed via three-component condensation of terephthalic aldehyde, 4-chloroacetoacetic ester, and ureas under Biginelli reaction conditions. Interaction of the obtained precursors that contain two highly reactive binucleophilic groups with primary amines leads to bis-heterocyclization with formation of (1,4-phenylene)-bis(pyrrolo[3,4-d]pyrimidine-2,5-diones).
AB - A one-pot synthesis of diethyl 4,4′-(1,4-phenylene)bis[6- (chloromethyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates] is proposed via three-component condensation of terephthalic aldehyde, 4-chloroacetoacetic ester, and ureas under Biginelli reaction conditions. Interaction of the obtained precursors that contain two highly reactive binucleophilic groups with primary amines leads to bis-heterocyclization with formation of (1,4-phenylene)-bis(pyrrolo[3,4-d]pyrimidine-2,5-diones).
KW - Biginelli reaction
KW - Bis-heterocyclization
KW - DHPM
KW - Multicomponent reactions
UR - http://www.scopus.com/inward/record.url?scp=78651062594&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=78651062594&partnerID=8YFLogxK
U2 - 10.1007/s00706-010-0354-9
DO - 10.1007/s00706-010-0354-9
M3 - Article
AN - SCOPUS:78651062594
SN - 0026-9247
VL - 141
SP - 997
EP - 1000
JO - Monatshefte fur Chemie
JF - Monatshefte fur Chemie
IS - 9
ER -