Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 8288-8298 |
| Number of pages | 11 |
| Journal | European Journal of Organic Chemistry |
| Issue number | 36 |
| DOIs | |
| Publication status | Published - 2013 Dec 1 |
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Keywords
- Amines
- Green chemistry
- Multicomponent reactions
- Nitroalkenes
- Quinones
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Synthesis of 3-substituted 2-aminonaphtho[2,3-b]furan-4,9-diones from 2-hydroxy-1,4-naphthoquinone and nitroalkenes. / Zanwar, Manoj R.; Kavala, Veerababurao; Gawande, Sachin D.; Kuo, Chun Wei; Kuo, Ting Shen; Chen, Mei Ling; He, Chiu Hui; Yao, Ching Fa.
In: European Journal of Organic Chemistry, No. 36, 01.12.2013, p. 8288-8298.Research output: Contribution to journal › Article
}
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
UR - http://www.scopus.com/inward/record.url?scp=84890441625&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84890441625&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201300996
DO - 10.1002/ejoc.201300996
M3 - Article
AN - SCOPUS:84890441625
SP - 8288
EP - 8298
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 36
ER -