Document Detail


Use of the curtius rearrangement of acryloyl azides in the synthesis of 3,5-disubstituted pyridines: mechanistic studies.
MedLine Citation:
PMID:  20828169     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A series of disubstituted pyridine derivatives was synthesized from the corresponding acryloyl azides by acetic acid-promoted cycloaddition. This represents a novel and convenient synthetic approach to the symmetric 3,5-disubstituted pyridines. The nature of the substituent on the double bond and the utilized solvent were found to be crucial to the yield of pyridines. The reactivity of the acid-promoted cycloaddition increases with the presence of aryl groups, such as phenyl and pyridinyl. We also explored the comprehensive mechanism by the acid-promoted cycloaddition of (13)C-labeled cinnamoyl azide. The symmetric 3,5-disubstituted pyridines were synthesized from acryloyl azides by acetic acid-promoted trimolecular condensation.
Authors:
Ta-Hsien Chuang; Yu-Chi Chen; Someshwar Pola
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  75     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2010 Oct 
Date Detail:
Created Date:  2010-09-24     Completed Date:  2011-01-04     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  6625-30     Citation Subset:  IM    
Affiliation:
School of Pharmacy, China Medical University, Taichung, 40402, Taiwan, Republic of China. thchuang@mail.cmu.edu.tw
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MeSH Terms
Descriptor/Qualifier:
Acetic Acid / chemistry*
Azides / chemistry*
Cyclization
Molecular Structure
Pyridines / chemical synthesis*,  chemistry
Stereoisomerism
Chemical
Reg. No./Substance:
0/Azides; 0/Pyridines; 64-19-7/Acetic Acid

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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