A SIMPLE AND EFFECTIVE METHOD FOR THE REDUCTION OF ACYL SUBSTITUTED HETEROCYCLIC 1,3-DICARBONYL COMPOUNDS TO ALKYL DERIVATIVES BY ZINC - ACETIC-ACID - HYDROCHLORIC-ACID

被引：11

作者：

KAPPE, T

AIGNER, R

ROSCHGER, P

SCHNELL, B

STADLBAUER, W

机构：

[1] Organic Synthesis Group, Institute of Organic Chemistry, Karl-Franzens-University of Graz, A-8010 Graz

来源：

TETRAHEDRON | 1995年 / 51卷 / 47期

关键词：

D O I：

10.1016/0040-4020(95)00733-O

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Acyl-4-hydroxy-2(1H)-quinolones (1a-k) were reduced in good yields (66-97%) to 3-alkyl-4-hydroxy-2(1H)-quinolinones (2a-k) using zinc powder (particle size <45 mu M) in acetic acid/hydrochloric acid. This method could be transformed to 3-acetyl-4-hydroxy-coumarin (1l), 3-acetyl-4-hydroxy-2-pyranone (3a) and 3-acetyl-4-hydroxy-2(1H)-pyridinone (3b), which yielded the 3-ethyl derivatives 21, 4a and 4b, respectively.

引用

页码：12923 / 12928

页数：6

共 41 条

[31] ROSCHGER P, 1988, THESIS K FRANZENS U
[32] SCHNELL B, 1994, THESIS K FRANZENS U
[33] REDUCTION OF ALPHA-PYRONE DERIVATIVES WITH BORANE-METHYL SULFIDE COMPLEX
SHIMIZU, T
HIRANUMA, S
WATANABE, T
[J]. HETEROCYCLES, 1993, 36 (11) : 2445 - 2450
[34] SILVESTRI R, 1994, IL FARMACO, V49, P625
[35] 2-ACETYLCYCLOHEXANE-1-3-DIONE
SMITH, H
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1953, (MAR): : 803 - 810
[36] HALOGENATION REACTIONS IN POSITION-3 OF QUINOLINE-2,4-DIONE SYSTEMS BY ELECTROPHILIC SUBSTITUTION AND HALOGEN EXCHANGE
STADLBAUER, W
LASCHOBER, R
LUTSCHOUNIG, H
SCHINDLER, G
KAPPE, T
[J]. MONATSHEFTE FUR CHEMIE, 1992, 123 (6-7): : 617 - 636
[37] THE ANTIBACTERIAL PROPERTIES OF COMPOUNDS CONTAINING THE TRICARBONYLMETHANE GROUP .4. SYNTHESES OF 3-ALKYLATED OR 3-ACYLATED 4-HYDROXYCOUMARINS AND OF A RELATED PYRONE
UKITA, T
NOJIMA, S
MATSUMOTO, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (11) : 5143 - 5144
[38] REDUCTION OF ENOLS - NEW SYNTHESIS OF CERTAIN METHOXYBENZSUBERENES VIA HYDROGENATION OF DEHYDROACETIC ACIDS
WALKER, GN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (13) : 3201 - 3205
[39] WOLF T, 1974, THESIS K FRANZENS U
[40] ZIEGLER E, 1955, MONATSH CHEM, V86, P29

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