Synthesis of 1,4-dihydropyridines by regioselective additions of benzylic zinc bromides to pyridinium salts and their aromatizations to 4-benzylpyridines

Article abstract of DOI:10.1080/00397919708004198

Benzylic zinc reagents add with high regioselectivity to 1-(phenoxycarbonyl) salts of methyl nicotinate to yield methyl-1-(phenoxycarbonyl)-4-benzyl-1,4-dihydronicotinates. The dihydronicotinates on heating with sulfur in decalin afford methyl 4-benzylnicotinates.

Full text of DOI:10.1080/00397919708004198

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Synthesis of 1,4-
Dihydropyridines by
Regioselective Additions
of Benzylic Zinc Bromides
to Pyridinium Salts and
Their Aromatizations to 4-
Benzylpyridines
A. Paul Krapcho a , David J. Waterhouse a ,
Abdelhakim Hammach a , Roberto Di Domenico
b , Ernesto Menta b , Ambrogio Oliva b & Silvano
Spinelli b
a Department of Chemistry , University of
Vermont , Burlington, VT, 05405, USA
b Boehringer Mannheim Italia, Research Center ,
Monza, 20052, Italy
Published online: 22 Aug 2006.
To cite this article: A. Paul Krapcho , David J. Waterhouse , Abdelhakim
Hammach , Roberto Di Domenico , Ernesto Menta , Ambrogio Oliva & Silvano
Spinelli (1997) Synthesis of 1,4-Dihydropyridines by Regioselective Additions
of Benzylic Zinc Bromides to Pyridinium Salts and Their Aromatizations to
4-Benzylpyridines, Synthetic Communications: An International Journal for
Rapid Communication of Synthetic Organic Chemistry, 27:5, 781-794, DOI:
10.1080/00397919708004198

To link to this article: http://dx.doi.org/10.1080/00397919708004198
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