Home | My Profile | Contact Us
Research Trends Products  |   order gateway  |   author gateway  |   editor gateway  
ID:
Password:
Register | Forgot Password

Author Resources
 Author Gateway
 Article submission guidelines

Editor Resources
 Editor/Referee Gateway

Agents/Distributors
 Regional Subscription Agents/Distributors
 
Trends in Heterocyclic Chemistry   Volumes    Volume 5 
Abstract
Recent interrelationships in the chemistries of thienopyridines, benzopyridines, and benzothiophenes
LeRoy H. Klemm
Pages: 37 - 55
Number of pages: 19
Trends in Heterocyclic Chemistry
Volume 5 

Copyright © 1997 Research Trends. All rights reserved

ABSTRACT
 
In updating of an earlier paper, this review extends comparisons between the reported physicochemical properties (both experimental and theoretical) of the six aromatic thienopyridine systems and their benzopyridine and benzothiophene isosteres. Systems covered are primarily thieno[2,3-b]-, -[3,2-b]-, -[2,3-c]-, and -[3,2-c]pyridines (1-4, respectively), quinoline (Q), isoquinoline (IQ), and benzo[b]thiophene (BT), with very limited attention to the less stable thieno[3,4-b]- and -[3,4-c]pyridines. Dipole moments, l3C nmr measurements, mass spectra, molecular complexation, and keto-enol tautomerism are discussed. Reissert, Reissert-Henze, and Hamana reactions which introduce carbon-bonded substituents into the pyridine ring, and addition reactions to the thiophene ring of sulfones are covered. Also electrophilic reactions, nucleophilic displacements, lithiation, and (for thienopyridine 1 only) free radical substitutions are noted. With few exceptions, notably the positions of substitution (α for Q, γ for 1) in the Hamana reaction and the differences in reactivities of the α- and γ-chloro groups toward nucleophilic displacement (γ α for Q, γ > α for 1 and 2), the generalization that the chemistries of 1-4 are interpretable as amalgamations of those of their isosteric reference compounds (Q or IQ, and BT) is strongly supported. Even in a sample of a fossil fuel, GC-MS analysis implies that one finds structurally closely related condensed thiophene and thienopyridine components. Moreover, various examples of thienopyridine isosteres of biologically active molecules are known or suspected agonists or antagonists.
 
 
Buy this Article


 
search


E-Commerce
Buy this article
Buy this volume
Subscribe to this title
Shopping Cart

Quick Links
Login
Search Products
Browse in Alphabetical Order : Journals
Series/Books
Browse by Subject Classification : Journals
Series/Books

Miscellaneous
Ordering Information Ordering Information
Downloadable forms Downloadable Forms