2017年8月27日日曜日

Iodine Mediated Benzimidazole Cyclizations 2017


A New Report for Benzimidazole Synthesis

Reveals the Utility of I2 + K2CO3 in CH2Cl2.



http://pubs.acs.org/doi/pdfplus/10.1021/acs.oprd.7b00193






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Quinolone Synthesis 2017


Scalable and Practical Synthesis of Halo Quinolin-2(1H)-ones and Quinolines

Chemistry Process R&D, Actelion Pharmaceuticals Ltd., Gewerbestrasse 16, CH-4123 Allschwil, Switzerland
Org. Process Res. Dev., 2017, 21 (7), pp 1003–1011
DOI: 10.1021/acs.oprd.7b00124
Publication Date (Web): June 22, 2017
Copyright © 2017 American Chemical Society
*E-mail: Gunther.Schmidt@idorsia.com. Telephone: +41 61 565 8028.

Abstract

Abstract Image
 
 
A practical and scalable synthesis of halo quinolin-2(1H)-ones is presented. The heterocycles are easily accessed from inexpensive halo anilines in a two-step sequence. The anilines are acylated with methyl 3,3-dimethoxypropionate under basic conditions in quantitative yields. The crude amides undergo cyclization in sulfuric acid to the desired halo quinolin-2(1H)-ones in 28–93% yield (2 steps). The synthetic sequence was successfully applied on 800 g scale. Anilines with strong electron withdrawing or electron donating groups were poor substrates for this procedure. 6-Iodoquinolin-2(1H)-one and 6-bromo-8-iodoquinolin-2(1H)-one were further functionalized to obtain quinolines substituted with various functional groups.
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.oprd.7b00124.
  • Experimental procedures and analytical data for compounds 2 and 3. (PDF)

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2017年8月21日月曜日

Aldehyde C-H Arylation 2017


Direct Acylation of Aromatic Compounds

By the Activation of Aldehede with Metal Catalysts;

 

 

http://pubs.acs.org/doi/abs/10.1021/jacs.7b07078?src=recsys



Abstract

Abstract Image
 
 
 
A mechanism that enables direct aldehyde C–H functionalization has been achieved via the synergistic merger of photoredox, nickel, and hydrogen atom transfer catalysis. This mild, operationally simple protocol transforms a wide variety of commercially available aldehydes, along with aryl or alkyl bromides, into the corresponding ketones in excellent yield. This C–H abstraction coupling technology has been successfully applied to the expedient synthesis of the medicinal agent haloperidol.
 
 
 

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2017年8月15日火曜日

Sequential Oxidative Conversion of Alchols into Amaides



Ruthenium-Catalyzed Oxidation of Alcohols into Amides


 
 
Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, U.K., and GlaxoSmithKline Research and Development, Gunnels Wood Road, Stevenage, SG1 2NY, U.K.
Org. Lett., 2009, 11 (12), pp 2667–2670
DOI: 10.1021/ol900723v
Publication Date (Web): May 15, 2009
Copyright © 2009 American Chemical Society
j.m.j.williams@bath.ac.uk, †
University of Bath.
, ‡
GlaxoSmithKline Research and Development.

Abstract

Abstract Image
 
 
The synthesis of secondary amides from primary alcohols and amines has been developed using commercially available [Ru(p-cymene)Cl2]2 with bis(diphenylphosphino)butane (dppb) as the catalyst.

Supporting Information

Details of experimental procedures and characterization data are provided. This material is available free of charge via the Internet at http://pubs.acs.org.
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