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Microwave‐assisted nucleophilic cleavage of 5,7‐dimethyl‐2‐phenyl‐1‐oxo‐l H ‐pyrazolo[ 1,2‐ a ]pyrazol‐4‐ylium‐3‐olate to α‐phenylmalonamides
Author(s) -
Lynch Daniel E.,
Spicer Gillian E.,
Mcclenaghan Ian
Publication year - 2005
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570420716
Subject(s) - chemistry , aniline , nucleophile , cleavage (geology) , medicinal chemistry , mass spectrometry , solvent , nuclear magnetic resonance spectroscopy , organic chemistry , catalysis , geotechnical engineering , chromatography , fracture (geology) , engineering
Three α‐phenylmalonamides have been prepared by the selective nucleophilic cleavage of 5,7‐dimethyl‐2‐phenyl‐1‐oxo‐1 H ‐pyrazolo[1,2‐ a ]pyrazol‐4‐ylium‐3‐olate in solventless microwave syntheses. The three weak nucleophiles employed were aniline, p ‐chloroaniline and m ‐toluidine. The α‐phenylmalonamides of these three aniline derivatives could not be prepared using the previously reported solvent syntheses via 3‐oxopyrazolo[1,2‐ a ]pyrazol‐8‐ylium‐1‐olates. All products were characterised using, infrared spectroscopy, 1 H nmr and electrospray mass spectrometry. The single crystal X‐ray structures of the starting pyrazolo‐[1,2‐ a ]pyrazole and α‐phenylmalon‐ m ‐toluidide are also reported.