CONVERSION OF N-ACYL-2,3-DIHYDRO-4-PYRIDONES TO 4-CHLORO-1,2-DIHYDROPYRIDINES USING THE VILSMEIER REAGENT

被引：31

作者：

ALAWAR, RS ^{[1
]}

JOSEPH, SP ^{[1
]}

COMINS, DL ^{[1
]}

机构：

[1] N CAROLINA STATE UNIV,DEPT CHEM,RALEIGH,NC 27695

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 50期

关键词：

D O I：

10.1016/0040-4039(93)88003-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Acyl-2,3-dihydro-4-pyridones are converted to 1-acyl-4-chloro-1,2-dihydropyridines in one step using one equivalent of Vilsmeier reagent. This conversion was utilized in an asymmetric synthesis of (-)-coniine.

引用

页码：7635 / 7638

页数：4

共 31 条

[1] A HIGHLY STEREOCONTROLLED, 4-STEP SYNTHESIS OF (+/-)-LASUBINE-II
BROWN, JD
FOLEY, MA
COMINS, DL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) : 7445 - 7447
[2] SYNTHESIS AND SYNTHETIC UTILITY OF 1-ACYL-5-(TRIALKYLSILYL)-1,2-DIHYDROPYRIDINES - SYNTHESIS OF (+/-)-ELAEOKANINE-A
COMINS, DL
MYOUNG, YC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) : 292 - 298
[3] REGIOSELECTIVE ADDITION OF NUCLEOPHILES TO 1-(PHENOXYCARBONYL)-3-TRIALKYLSTANNYLPYRIDINIUM SALTS
COMINS, DL
MANTLO, NB
[J]. TETRAHEDRON LETTERS, 1987, 28 (07) : 759 - 762
[4] THE ADDITION OF ALKYLZINC IODIDES TO 1-(PHENOXYCARBONYL)PYRIDINIUM SALTS
COMINS, DL
OCONNOR, S
[J]. TETRAHEDRON LETTERS, 1987, 28 (17) : 1843 - 1846
[5] AN EFFICIENT ASYMMETRIC-SYNTHESIS OF 1-ACYL-2-ALKYL-1,2-DIHYDROPYRIDINES
COMINS, DL
HONG, H
SALVADOR, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (26) : 7197 - 7199
[6] REGIOSPECIFIC ALPHA-ALKYLATION OF 4-CHLORO(BROMO)PYRIDINE
COMINS, DL
MANTLO, NB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (22) : 4410 - 4411
[7] THE ADDITION OF ALKYLZINC IODIDES TO 1-(PHENOXYCARBONYL)-2,3-DIHYDROPYRIDINIUM SALTS - A SYNTHESIS OF 2-ALKYL-DELTA-3-PIPERIDINES
COMINS, DL
FOLEY, MA
[J]. TETRAHEDRON LETTERS, 1988, 29 (51) : 6711 - 6714
[8] CHIRAL DIHYDROPYRIDONES AS SYNTHETIC INTERMEDIATES - ASYMMETRIC-SYNTHESIS OF (+)-ELAEOKANINE-A AND (+)-ELAEOKANINE-C
COMINS, DL
HONG, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (17) : 6672 - 6673
[9] ASYMMETRIC-SYNTHESIS OF 2-ALKYL(ARYL)-2,3-DIHYDRO-4-PYRIDONES BY ADDITION OF GRIGNARD-REAGENTS TO CHIRAL 1-ACYL-4-METHOXYPYRIDINIUM SALTS
COMINS, DL
GOEHRING, RR
JOSEPH, SP
OCONNOR, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) : 2574 - 2576
[10] STEREOCONTROLLED PREPARATION OF CIS-2,6-DIALKYLPIPERIDINE AND TRANS-2,6-DIALKYLPIPERIDINE VIA 1-ACYLDIHYDROPYRIDINE INTERMEDIATES - SYNTHESIS OF (+/-)-SOLENOPSIN-A AND (+/-)-DIHYDROPINIDINE
COMINS, DL
WEGLARZ, MA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) : 2506 - 2512

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