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Domino Reaction of Naphthoquinone and β‐Arylpyruvic Acids: Synthesis of 3‐(Naphthoquinonyl)naphthofuran‐2(3 H )‐ones
Author(s) -
OrtizRojano Laura,
MartínezMingo Mario,
GarcíaGarcía Carolina,
Ribagorda María,
Carreño M. Carmen
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701656
Subject(s) - chemistry , nucleophile , 1,4 naphthoquinone , naphthoquinone , domino , reactivity (psychology) , aryl , combinatorial chemistry , acceptor , michael reaction , organic chemistry , catalysis , alternative medicine , physics , pathology , condensed matter physics , medicine , alkyl
Unprecedented reactivity between naphthoquinone and β‐aryl‐α‐keto acids has been uncovered. The process combined the redox properties of the Michael‐type naphthoquinone acceptor with arylpyruvic acid, which is acting first as a C 3 ‐donor pro‐nucleophile and later as an acylating agent. As a result, densely substituted naphthofuran‐2(3 H )‐ones were generated in a mild and simple one‐pot reaction.