Journal
ORGANIC LETTERS
Volume 22, Issue 2, Pages 542-546Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b04297
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Funding
- Department of Science and Technology (DST), New Delhi, India under a DST - INSPIRE faculty scheme [DST/INSPIRE/04/2015/002987]
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An efficient palladium-catalyzed approach to access various functionalized (Z)-3-benzylidene-isoindoline-1-ones and (Z)-3-benzylidene(imino)isobenzofuranones via a denitrogenative tandem alkynylation/cyclization reaction of 1,2,3-benzotriazin-4(3H)-ones with aromatic terminal alkynes is described. Furthermore, a denitrogenative ortho-alkynylation reaction of 1,2,3-benzotriazinones with aliphatic terminal alkynes is also developed. The reaction proceeds through a five-membered Wazapalladacyclic intermediate with the extrusion of a nitrogen molecule. The significance of the reaction is also demonstrated by a one-pot synthesis of (Z)-3-benzylideneisobenzofuran-1(3H)-one derivatives in good to high yields.
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