Abstract
An efficient 2·3-component reaction (2·3CR; a 2-component reaction followed, in one pot, by a3-component reaction) is presented for the synthesis of isoxazolino-β-ketoamides. This 2·3CR proceeds by (i) a Meldrum's acid-generated acyl ketene, which is trapped by an amine to form a β-ketoamide intermediate in a 2CR followed, in one pot, by (ii) a Mannich reaction followed by elimination of dimethyl amine·HCl to generate an α,β-unsaturated β-ketoamide dipolarophile that reacts in a nitrile oxide 1,3-dipolar cycloaddition reaction. This one-pot 2·3CR process delivers the targeted isoxazolino-β-ketoamide product. A total of 72 compounds are presented, all of which have been submitted to the NIH Molecular Libraries Small Molecule Repository for high-throughput biological screening.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 85-88 |
| Number of pages | 4 |
| Journal | ACS Combinatorial Science |
| Volume | 14 |
| Issue number | 2 |
| DOIs | |
| State | Published - Feb 13 2012 |
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Keywords
- 2·3-component reaction
- isoxazolino-β-ketoamide product
- isoxazolino-β-ketoamides
- one pot
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Expedient synthesis of a 72-membered isoxazolino-β-ketoamide library by a 2·3-component reaction. / Knapp, John M.; Zhu, Jie S.; Wood, Alex B.; Kurth, Mark J.
In: ACS Combinatorial Science, Vol. 14, No. 2, 13.02.2012, p. 85-88.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Expedient synthesis of a 72-membered isoxazolino-β-ketoamide library by a 2·3-component reaction
AU - Knapp, John M.
AU - Zhu, Jie S.
AU - Wood, Alex B.
AU - Kurth, Mark J.
PY - 2012/2/13
Y1 - 2012/2/13
N2 - An efficient 2·3-component reaction (2·3CR; a 2-component reaction followed, in one pot, by a3-component reaction) is presented for the synthesis of isoxazolino-β-ketoamides. This 2·3CR proceeds by (i) a Meldrum's acid-generated acyl ketene, which is trapped by an amine to form a β-ketoamide intermediate in a 2CR followed, in one pot, by (ii) a Mannich reaction followed by elimination of dimethyl amine·HCl to generate an α,β-unsaturated β-ketoamide dipolarophile that reacts in a nitrile oxide 1,3-dipolar cycloaddition reaction. This one-pot 2·3CR process delivers the targeted isoxazolino-β-ketoamide product. A total of 72 compounds are presented, all of which have been submitted to the NIH Molecular Libraries Small Molecule Repository for high-throughput biological screening.
AB - An efficient 2·3-component reaction (2·3CR; a 2-component reaction followed, in one pot, by a3-component reaction) is presented for the synthesis of isoxazolino-β-ketoamides. This 2·3CR proceeds by (i) a Meldrum's acid-generated acyl ketene, which is trapped by an amine to form a β-ketoamide intermediate in a 2CR followed, in one pot, by (ii) a Mannich reaction followed by elimination of dimethyl amine·HCl to generate an α,β-unsaturated β-ketoamide dipolarophile that reacts in a nitrile oxide 1,3-dipolar cycloaddition reaction. This one-pot 2·3CR process delivers the targeted isoxazolino-β-ketoamide product. A total of 72 compounds are presented, all of which have been submitted to the NIH Molecular Libraries Small Molecule Repository for high-throughput biological screening.
KW - 2·3-component reaction
KW - isoxazolino-β-ketoamide product
KW - isoxazolino-β-ketoamides
KW - one pot
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U2 - 10.1021/co200199h
DO - 10.1021/co200199h
M3 - Article
C2 - 22181856
AN - SCOPUS:84863132019
VL - 14
SP - 85
EP - 88
JO - ACS Combinatorial Science
JF - ACS Combinatorial Science
SN - 2156-8952
IS - 2
ER -