Abstract
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.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 7459-7468 |
| Number of pages | 10 |
| Journal | Tetrahedron |
| Volume | 51 |
| Issue number | 27 |
| DOIs | |
| State | Published - Jul 3 1995 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Synthesis and regioselective [4+2] cycloaddition/nucleophilic reactions of N-arylamino-1:3-diaza-1:3-butadienes with ketenes and accompanying rearrangements. / Dey, Paramita D.; Sharma, Arun; Rai, Sachchida N.; Mahajan, Mohinder P.
In: Tetrahedron, Vol. 51, No. 27, 03.07.1995, p. 7459-7468.Research output: Contribution to journal › Article
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.
UR - http://www.scopus.com/inward/record.url?scp=0029077398&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0029077398&partnerID=8YFLogxK
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 -