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

Malose J. Mphahlele; Omankutty Gheevarghese; Nkosinathi F.H. Makhubela

doi:10.1080/10426500008076551

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

Malose J. Mphahlele^*
, Omankutty Gheevarghese
, Nkosinathi F.H. Makhubela

^*Corresponding author for this work

Biology

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	303-314
Number of pages	12
Journal	Phosphorus, Sulfur and Silicon and Related Elements
Volume	166
DOIs	https://doi.org/10.1080/10426500008076551
Publication status	Published - 2000

Keywords

4-amino-2-arylquinolines
Neber rearrangement
O-mesyloxime 2-aryl-1; 2; 3; 4-tetrahydro-1-methylsulfonyl-4-quinolone derivatives

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10.1080/10426500008076551

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@article{626968f14f5044a2b2c161c7a0600727,

title = "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",

abstract = "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.",

keywords = "4-amino-2-arylquinolines, Neber rearrangement, O-mesyloxime 2-aryl-1; 2; 3; 4-tetrahydro-1-methylsulfonyl-4-quinolone derivatives",

author = "Mphahlele, \{Malose J.\} and Omankutty Gheevarghese and Makhubela, \{Nkosinathi F.H.\}",

note = "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.",

year = "2000",

doi = "10.1080/10426500008076551",

language = "English",

volume = "166",

pages = "303--314",

journal = "Phosphorus, Sulfur and Silicon and Related Elements",

issn = "1042-6507",

}

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. / Mphahlele, Malose J.; Gheevarghese, Omankutty; Makhubela, Nkosinathi F.H.
In: Phosphorus, Sulfur and Silicon and Related Elements, Vol. 166, 2000, p. 303-314.

Research output: Contribution to journal › Article › peer-review

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 - https://www.scopus.com/pages/publications/0034355363

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 Related Elements

JF - Phosphorus, Sulfur and Silicon and Related Elements

ER -

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

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