SYNTHESIS OF BICYCLIC PYRIDONE AND DIHYDROPYRIDONE ANALOGS OF BETA-LACTAM ANTIBIOTICS

被引：28

作者：

CAPPS, NK

DAVIES, GM

LOAKES, D

MCCABE, RW

YOUNG, DW ^{[1
]}

机构：

[1] UNIV SUSSEX,SCH CHEM & MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND

[2] ICI PHARMACEUT PLC,MACCLESFIELD SK10 4TG,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 12期

关键词：

D O I：

10.1039/p19910003077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensation of the vinylogous urethanes 2, 26, 28 and 29 with acrylates, haloacrylates and propiolic acid has afforded easy access to bicyclic dihydropyridone and pyridone analogues of cephalosporins, carbapenams, penicillins and bisnorpenicillins. Synthesis of the pyridone is accompanied, in one instance, by an interesting cyclisation to the glutaconic anhydride 23 and significant differences in tautomeric behaviour have been found between the five-membered vinylogous urethanes 28 and 29 and their six-membered counterparts 2.

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页码：3077 / 3086

页数：10

相关论文

共 19 条

[1]

BALDWIN JE, 1991, J ANTIBIOT, V44, P1

[2] STUDIES RELATED TO CEPHALOSPORIN C .2. SYNTHETICAL ROUTE TO 5,6-DIHYDRO-4H-1,3-THIAZINES + 3,6-DIHYDRO-2H-1,3-THIAZINES [J].

BARRETT, GC ;

EGGERS, SH ;

EMERSON, TR ;

LOWE, G .

JOURNAL OF THE CHEMICAL SOCIETY, 1964, (FEB) :788-&

[3] ATTEMPTS AT SYNTHESIS OF PENICILLIN RING-SYSTEM BY TRANSANNULAR REACTIONS [J].

BENN, MH ;

MITCHELL, RE .

CANADIAN JOURNAL OF CHEMISTRY, 1972, 50 (14) :2195-&

[4]

CAPPS NK, 1984, THESIS SUSSEX

[5] STUDIES RELATED TO CEPHALOSPORIN C .3. A SYNTHETICAL ROUTE TO 6H-1,3-THIAZINES AND SYNTHESIS OF A NEW FRAGMENTATION PRODUCT OF A CEPHALOSPORANIC ACID DERIVATIVE [J].

EGGERS, SH ;

KANE, VV ;

LOWE, G .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (FEB) :1262-&

[6] TOTAL SYNTHESIS OF THE ANGIOTENSIN-CONVERTING ENZYME INHIBITOR-A58365A - ON THE USE OF PYROGLUTAMATE AS A CHIRAL EDUCT [J].

FANG, FG ;

DANISHEFSKY, SJ .

TETRAHEDRON LETTERS, 1989, 30 (28) :3621-3624

[7] ALPHA-TETRONIC ACIDS + 3,6-DIHYDRO-2H-1,3-THIAZINE RING [J].

GREEN, DM ;

LONG, AG ;

TURNER, AF ;

MAY, PJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1964, (FEB) :766-&

[8] NOVEL AND EFFICIENT PHOTOCHEMICAL-REARRANGEMENT OF 1,3-THIAZINE DERIVATIVES [J].

HITCHCOCK, PB ;

MCCABE, RW ;

YOUNG, DW ;

DAVIES, GM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (12) :608-609

[9] STRUCTURE ELUCIDATION OF A58365A AND A58365B, ANGIOTENSIN CONVERTING ENZYME-INHIBITORS PRODUCED BY STREPTOMYCES-CHROMOFUSCUS [J].

HUNT, AH ;

MYNDERSE, JS ;

SAMLASKA, SK ;

FUKUDA, DS ;

MACIAK, GM ;

KIRST, HA ;

OCCOLOWITZ, JL ;

SWARTZENDRUBER, JK ;

JONES, ND .

JOURNAL OF ANTIBIOTICS, 1988, 41 (06) :771-774

[10] CONFIGURATION OF CHLOROACRYLIC ACIDS AMIDES ESTERS AND NITRILES BY NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY [J].

KURTZ, AN ;

BILLUPS, WE ;

GREENLEE, RB ;

HAMIL, HF ;

PACE, WT .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (09) :3141-&