TY - JOUR
T1 - Synthesis of 3-substituted 2-aminonaphtho[2,3-b]furan-4,9-diones from 2-hydroxy-1,4-naphthoquinone and nitroalkenes
AU - Zanwar, Manoj R.
AU - Kavala, Veerababurao
AU - Gawande, Sachin D.
AU - Kuo, Chun Wei
AU - Kuo, Ting Shen
AU - Chen, Mei Ling
AU - He, Chiu Hui
AU - Yao, Ching Fa
PY - 2013/12/1
Y1 - 2013/12/1
N2 - 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. 3-Substituted 2-aminonaphtho[2,3-b]furan-4,9-diones have been synthesized from 2-hydroxy-1,4-naphthoquinone and nitro alkenes under aqueous conditions. In this methodology, a nitro moiety is converted into an amino functionality in the absence of a reducing agent. The same products were obtained from a three-component reaction involving aldehydes, 2-hydroxy-1,4-naphthoquinone, and nitromethane.
AB - 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. 3-Substituted 2-aminonaphtho[2,3-b]furan-4,9-diones have been synthesized from 2-hydroxy-1,4-naphthoquinone and nitro alkenes under aqueous conditions. In this methodology, a nitro moiety is converted into an amino functionality in the absence of a reducing agent. The same products were obtained from a three-component reaction involving aldehydes, 2-hydroxy-1,4-naphthoquinone, and nitromethane.
KW - Amines
KW - Green chemistry
KW - Multicomponent reactions
KW - Nitroalkenes
KW - Quinones
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U2 - 10.1002/ejoc.201300996
DO - 10.1002/ejoc.201300996
M3 - Article
AN - SCOPUS:84890441625
SP - 8288
EP - 8298
JO - Justus Liebigs Annalen der Chemie
JF - Justus Liebigs Annalen der Chemie
SN - 0075-4617
IS - 36
ER -