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Silver(I)‐Catalyzed Tandem 1,3‐Acyloxy Migration/Mannich‐type Addition/Elimination of the Sulfonyl Group of N ‐Sulfonylhydrazone‐propargylic Esters to 5,6‐Dihydropyridazin‐4‐one Derivatives
Author(s) -
Zhang Zhen,
Shi Min
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103404
Subject(s) - sulfonyl , chemistry , catalysis , tandem , group (periodic table) , medicinal chemistry , organic chemistry , combinatorial chemistry , stereochemistry , alkyl , materials science , composite material
The addition of nucleophiles to CN bonds offers a highly efficient synthetic strategy for accessing nitrogen‐containing molecules.1 Among the well‐developed addition reactions, such as the highly efficient Mannich reaction, various CH bond‐activated compounds including carboxylic acid derivatives, nitroalkanes, and terminal alkynes have been applied as nucleophiles to achieve different classes of amines.2 However, employing new nucleophiles without activated CH bonds, such as internal alkynes and allenic esters are limited when using metal catalysts.3 Herein, we wish to report a new addition of allenic esters to CN bonds initiated by a silver‐catalyzed 1,3‐migration of propargylic esters.