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Unprecedented Cu-Catalyzed Coupling of Internal 1,3-Diynes with Azides: One-Pot Tandem Cyclizations Involving 1,3-Dipolar Cycloaddition and Carbocyclization Furnishing Naphthotriazoles (†).
MedLine Citation:
PMID:  21591629     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
A one-pot protocol for the synthesis of triazole-annulated polyheterocycles via metal-catalyzed coupling of internal 1,4-disubstituted 1,3-diynes and organic azides has been described. The mechanistic rationale for the reaction suggests tandem cyclizations involving copper-catalyzed cycloaddition and 6-endo carbocyclization reactions. The cascade cyclization leads to an increase in molecular complexity to furnish naphtho[1,2-d]triazoles in satisfactory yields. The generality of the method has been demonstrated by using a series of aromatic/aliphatic azides and symmetrical internal 1,3-diynes.
Authors:
Anil K Mandadapu; Sudhir K Sharma; Sahaj Gupta; Deevi G Venkata Krishna; Bijoy Kundu
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-5-17
Journal Detail:
Title:  Organic letters     Volume:  -     ISSN:  1523-7052     ISO Abbreviation:  -     Publication Date:  2011 May 
Date Detail:
Created Date:  2011-5-19     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Medicinal Chemistry Division and Sophisticated Analytical Instrument Facility, Central Drug Research Institute, CSIR Lucknow 226 001, India.
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