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Boron Trifluoride‐Promoted Indium(III) Triflate‐Catalyzed Sequential One‐Pot Synthesis of (1,2‐Diaryl‐2‐oxoethyl)malonates from trans ‐2‐Aryl‐3‐nitrocyclopropane‐1,1‐dicarboxylates and Activated Arenes
Author(s) -
Selvi Thangavel,
Srinivasan Kannupal
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500143
Subject(s) - chemistry , boron trifluoride , trifluoromethanesulfonate , catalysis , adduct , medicinal chemistry , aryl , carbazole , pyrrole , organic chemistry , alkyl
A sequential one‐pot synthesis of Michael adducts of aroylmethylidenemalonates with activated aromatics is described. The method involves treatment of trans ‐2‐aryl‐3‐nitro‐cyclopropane‐1,1‐dicarboxylates with boron trifluoride etherate to form aroylmethylidenemalonates in situ and then addition of activated aromatics such as indoles, carbazole, pyrrole, thiophenes, methoxybenzenes and benzodioxole followed by a catalytic amount of indium(III) triflate to the same reaction vessel. To prove the synthetic potential of the resulting Michael adducts, one of the adducts was transformed into a pharmaceutically interesting dihydropyridazinone derivative.