TY - JOUR
T1 - Synthesis and regioselective [4+2] cycloaddition/nucleophilic reactions of N-arylamino-1:3-diaza-1:3-butadienes with ketenes and accompanying rearrangements
AU - Dey, Paramita D.
AU - Sharma, Arun
AU - Rai, Sachchida N.
AU - Mahajan, Mohinder P.
PY - 1995/7/3
Y1 - 1995/7/3
N2 - N-Arylamino-1:3-diaza-1:3-butadienes 4 are shown to undergo regioselective reactions with phenyl- and chloroketenes resulting in high yields of 3-aryl-2-methylthio6-phenyl-4(3H)-pyrimidinones 7. Similar reactions with bromo- and iodoketenes, resulted, via aziridinium intermediates 12, in good yields of 3-aryl-S-(N-arylamino)-2-methylthio-6-phenyl4(3H)-pyrimidinones 13, The mechanistic aspects of cycloadditions and semi-empirical AM1 calculations for these diazabutadienes are also reported.
AB - N-Arylamino-1:3-diaza-1:3-butadienes 4 are shown to undergo regioselective reactions with phenyl- and chloroketenes resulting in high yields of 3-aryl-2-methylthio6-phenyl-4(3H)-pyrimidinones 7. Similar reactions with bromo- and iodoketenes, resulted, via aziridinium intermediates 12, in good yields of 3-aryl-S-(N-arylamino)-2-methylthio-6-phenyl4(3H)-pyrimidinones 13, The mechanistic aspects of cycloadditions and semi-empirical AM1 calculations for these diazabutadienes are also reported.
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U2 - 10.1016/0040-4020(95)00372-F
DO - 10.1016/0040-4020(95)00372-F
M3 - Article
AN - SCOPUS:0029077398
VL - 51
SP - 7459
EP - 7468
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 27
ER -