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Synthesis of 3‐Substituted 2‐Aminonaphtho[2,3‐ b ]furan‐4,9‐diones from 2‐Hydroxy‐1,4‐Naphthoquinone and Nitroalkenes
Author(s) -
Zanwar Manoj R.,
Kavala Veerababurao,
Gawande Sachin D.,
Kuo ChunWei,
Kuo TingShen,
Chen MeiLing,
He ChiuHui,
Yao ChingFa
Publication year - 2013
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.201300996
Subject(s) - chemistry , nitromethane , naphthoquinone , aldehyde , furan , 1,4 naphthoquinone , combinatorial chemistry , organic chemistry , aqueous solution , medicinal chemistry , catalysis
The efficient base‐catalyzed synthesis of 3‐substituted 2‐aminonaphtho[2,3‐ b ]furan‐4,9‐dione derivatives from readily available precursors such as 2‐hydroxy‐1,4‐naphthoquinone and nitroalkenes under aqueous conditions is described. Interesting features of this methodology are the conversion of a nitro functionality into an amino functionality in the absence of a reducing agent and the development of a three component reaction for accessing the same product from an aldehyde, 2‐hydroxy‐1,4‐naphthoquinone and nitromethane.