A highly effective one-pot synthesis of quinolines from o-nitroarylcarbaldehydes

An-Hu Li; Eilaf Ahmed; Xin Chen; Matthew Cox; Andrew P. Crew; Han-Qing Dong; Meizhong Jin; Lifu Ma; Bijoy Panicker; Kam W. Siu; Arno G. Steinig; Kathryn M. Stolz; Paula A. R. Tavares; Brian Volk; Qinghua Weng; Doug Werner; Mark J. Mulvihill

doi:10.1039/B613775J

A highly effective one-pot synthesis of quinolines from o-nitroarylcarbaldehydes†

An-Hu Li,*^a Eilaf Ahmed,^a Xin Chen,^a Matthew Cox,^a Andrew P. Crew,^a Han-Qing Dong,^a Meizhong Jin,^a Lifu Ma,^a Bijoy Panicker,^a Kam W. Siu,^a Arno G. Steinig,^a Kathryn M. Stolz,^a Paula A. R. Tavares,^a Brian Volk,^a Qinghua Weng,^a Doug Werner^a and Mark J. Mulvihill*^a

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^a Department of Cancer Chemistry, OSI Pharmaceuticals, Inc., 1 Bioscience Park Drive, Farmingdale, NY, USA
E-mail: ali@osip.com, mmulvihill@osip.com
Fax: +1-631-845-5671
Tel: +1-631-962-0600

Abstract

A highly effective one-pot Friedländer quinoline synthesis using inexpensive reagents has been developed. o-Nitroarylcarbaldehydes were reduced to o-aminoarylcarbaldehydes with iron in the presence of catalytic HCl (aq.) and subsequently condensed in situ with aldehydes or ketones to form mono- or di-substituted quinolines in high yields (66–100%).

Organic & Biomolecular Chemistry

A highly effective one-pot synthesis of quinolines from o-nitroarylcarbaldehydes†

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A highly effective one-pot synthesis of quinolines from o-nitroarylcarbaldehydes

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