AN EFFICIENT SYNTHESIS OF 6-FORMYL-1,2-DIHYDRO-2-OXO-3-PYRIDINECARBOXYLIC ACID AND SOME CARBONYL DERIVATIVES OF IT AND ITS 6-ACETYL HOMOLOG

被引：11

作者：

SANCHEZ, JP

MICH, TF

HUANG, GG

机构：

[1] Parke-Davis Pharmaceutical Research, Division of Warner-Lambert Company, Ann Arbor, Michigan

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1994年 / 31卷 / 02期

关键词：

D O I：

10.1002/jhet.5570310207

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting with 1,1-dimethoxy-2-propanone (1), 6-formyl-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid (5a) has been prepared in large quantities by a highly efficient, 4-step synthesis. This compound, along with its one carbon homologue, 6-acetyl-1,2-dihydro-2-oxo-3-pyridinecarboxylic acid (5b) has been reacted with several carbonyl derivative forming reagents to provide a series of side chains for beta-lactams. Among these carbon derivatives are styrylamides which were prepared from Wittig and Horner-Emmons reagents. The preparation of the phosphonium salts and phosphonate esters is also described.

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页码：297 / 303

页数：7

相关论文

共 19 条

[1] CONDENSATIONS OF CARBONYL COMPOUNDS AT METHYL OR ALPHA-METHYLENE GROUP OF 6- OR 4-ALKYL-3-CYANO-2(1)-PYRIDONES THROUGH DIANIONS [J].

BOATMAN, S ;

HARRIS, TM ;

HAUSER, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (22) :5198-&

[2]

BOATMAN S, 1965, J ORG CHEM, V30, P3595

[3] OLEFIN SYNTHESIS WITH ORGANIC PHOSPHONATE CARBANIONS [J].

BOUTAGY, J ;

THOMAS, R .

CHEMICAL REVIEWS, 1974, 74 (01) :87-99

[4] FUNCTIONALIZATION OF SUBSTITUTED 2(1H)-PYRIDONE AND 4(1H)-PYRIDONE .3. THE PREPARATION OF SUBSTITUTED 6-VINYL-1,2-DIHYDRO-2-OXO-PYRIDINECARBOXYLIC AND 1,4-DIHYDRO-4-OXO-3-PYRIDINECARBOXYLIC ACIDS THROUGH THE CHEMISTRY OF PYRIDONE DIANIONS [J].

DEJOHN, D ;

DOMAGALA, JM ;

KALTENBRONN, JS ;

KROLLS, U .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (05) :1295-1302

[5] SEMI-SYNTHETIC PENICILLINS - A STRUCTURE-ACTIVITY STUDY OF A NEW SERIES OF ACYL AMINO-ACID PYRIDONE AND PYRIMIDONE AMOXICILLIN ANALOGS [J].

HASKELL, TH ;

WOO, PWK ;

NICOLAIDES, ED ;

HUTT, MP ;

HAUNG, GG ;

SANCHEZ, JP ;

DEJOHN, D ;

HEIFETZ, CL ;

KROLLS, U ;

LUNNEY, E ;

MICH, TF .

JOURNAL OF ANTIBIOTICS, 1981, 34 (07) :862-868

[6]

HASKELL TH, 1982, Patent No. 4311699

[7] CI-867, A NEW BROAD-SPECTRUM SEMI-SYNTHETIC PENICILLIN [J].

KALTENBRONN, JS ;

HASKELL, TH ;

DOUB, L ;

KNOBLE, J ;

DEJOHN, D ;

KROLLS, U ;

JENESEL, N ;

HUANG, GG ;

HEIFETZ, CL ;

FISHER, MW .

JOURNAL OF ANTIBIOTICS, 1979, 32 (06) :621-625

[8]

Maercker A., 1965, ORG REACTIONS, V14, P270

[9]

MARIELLA RP, 1960, ORG SYNTH COLL, V4, P210

[10] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF A NEW SEMI-SYNTHETIC CEPHALOSPORIN, CN-92,982 [J].

MICH, TF ;

HUANG, GG ;

WOO, PWK ;

SANCHEZ, JP ;

HEIFETZ, CL ;

SCHWEISS, D ;

KROLLS, U ;

HUTT, MP ;

CULBERTSON, TP ;

HASKELL, TH .

JOURNAL OF ANTIBIOTICS, 1980, 33 (11) :1352-1356