TY - JOUR
T1 - Unprecedented outcome of base-promoted neber rearrangement of O-Mesyloxime of 2-aryl-1,2,3,4-tetrahydro-1-methylsul fonyl-4-quinolone-synthesis of 4-amino-2-arylquinolines
AU - Mphahlele, Malose J.
AU - Gheevarghese, Omankutty
AU - Makhubela, Nkosinathi F.H.
N1 - Funding Information:
We thank the National Research Foundation for financial assistance and Dr P. Boshoff (Cape Technikon Mass Spectrometry Unit) and Mr. Richard M. Mampa (University of the North) for mass and NMR spectroscopic data, respectively.
PY - 2000
Y1 - 2000
N2 - O-Mesyloximes derived from 2-aryl-1,2,3,4-tetrahydro-1-methylsulfonyl-4-quinolones react with sodium ethoxide in ethanol to afford the 4-amino-2-arylquinolines in high yield. No traces of the 3-amino-2-aryl-4-quinolones expected from the Neber rearrangement of the substrates were detected or isolated from the reaction mixture. The structures of the products were determined using a combination of 1H NMR, 13C NMR, IR and mass spectroscopic techniques.
AB - O-Mesyloximes derived from 2-aryl-1,2,3,4-tetrahydro-1-methylsulfonyl-4-quinolones react with sodium ethoxide in ethanol to afford the 4-amino-2-arylquinolines in high yield. No traces of the 3-amino-2-aryl-4-quinolones expected from the Neber rearrangement of the substrates were detected or isolated from the reaction mixture. The structures of the products were determined using a combination of 1H NMR, 13C NMR, IR and mass spectroscopic techniques.
KW - 4-amino-2-arylquinolines
KW - Neber rearrangement
KW - O-mesyloxime 2-aryl-1; 2; 3; 4-tetrahydro-1-methylsulfonyl-4-quinolone derivatives
UR - http://www.scopus.com/inward/record.url?scp=0034355363&partnerID=8YFLogxK
U2 - 10.1080/10426500008076551
DO - 10.1080/10426500008076551
M3 - Article
AN - SCOPUS:0034355363
SN - 1042-6507
VL - 166
SP - 303
EP - 314
JO - Phosphorus, Sulfur and Silicon and the Related Elements
JF - Phosphorus, Sulfur and Silicon and the Related Elements
ER -