Regioselective Synthesis Of Α- And Γ-amino Quinolinyl Phosphonamides Using N-heterocyclic Phosphines (nhps)

Authors

M Shetty, University of Nevada, Las Vegas
H Huang, University of Nevada, Las VegasFollow
J Y. Kang, University of Nevada, Las VegasFollow

Document Type

Article

Publication Date

1-1-2018

Publication Title

Organic Letters

Publisher

American Chemical Society

Volume

20

Issue

3

First page number:

700

Last page number:

703

Abstract

A regioselective phosphonylation of quinolines for the synthesis of α-amino quinolinyl phosphonamides and γ-amino quinolinyl phosphonamides has been developed under mild reaction conditions. An NHP-thiourea enables selective synthesis of α-amino quinolinyl phosphonamides by a Reissert-type reaction, and an NHP-tosylamide affords γ-amino quinolinyl phosphonamides via a 1,4-conjugate addition reaction. The corresponding amino quinolinyl phosphonate adducts were obtained in moderate to excellent yields (up to 99% yield) and regioselectivities (up to 99:1) with good functional group tolerance. © 2018 American Chemical Society.

Language

English

Repository Citation

Shetty, M., Huang, H., Kang, J. Y. (2018). Regioselective Synthesis Of Α- And Γ-amino Quinolinyl Phosphonamides Using N-heterocyclic Phosphines (nhps). Organic Letters, 20(3), 700-703. American Chemical Society.
http://dx.doi.org/10.1021/acs.orglett.7b03829