TRANSFORMATIONS USING BENZYL 6-ISOCYANOPENICILLANATE

被引:16
作者
BENTLEY, PH [1 ]
CLAYTON, JP [1 ]
BOLES, MO [1 ]
GIRVEN, RJ [1 ]
机构
[1] PLYMOUTH POLYTECH,SCH MATH SCI,PLYMOUTH PL4 8AA,DEVONSHIRE,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 10期
关键词
D O I
10.1039/p19790002455
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preparation and C-6 epimerisation of benzyl 6α- isocyanopenicillanate is described. By utilising the activating influence of the isocyanide group and a subsequent conversion of this group into an amino-group under mild conditions, 6α-substituted penicillins were thereby prepared. Additionally, several novel rearrangements of these isocyanides are described.
引用
收藏
页码:2455 / 2467
页数:13
相关论文
共 33 条
[1]  
ALDERSSCHONBERG G, 1972, TETRAHEDRON LETT, P2911
[2]   SOME NEW ASPECTS IN CHEMISTRY OF 4-ALKYLIDENE-DELTA-2-THIAZOLIN-5-ONES [J].
BACHI, MD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (03) :310-&
[3]   6ALPHA-SUBSTITUTED PENICILLINS [J].
BENTLEY, PH ;
CLAYTON, JP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (07) :278-279
[4]   STRUCTURES OF AMPICILLIN - COMPARISON OF ANHYDRATE AND TRIHYDRATE FORMS [J].
BOLES, MO ;
GIRVEN, RJ .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1976, 32 (AUG15) :2279-2284
[5]   SYNTHESES BASED ON 1,2-SECOPENICILLINS .1. OXIDATION [J].
BRAIN, EG ;
EGLINGTON, AJ ;
NAYLER, JHC ;
PEARSON, MJ ;
SOUTHGATE, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (04) :447-451
[6]   SYNTHESES IN THE PENICILLIN FIELD .9. A SYNTHESIS OF SOME PENICILLAMINE ANALOGUES AND ATTEMPTS TO OBTAIN NEW TYPES OF PENICILLINS [J].
COOK, AH ;
HARRIS, G ;
POLLOCK, JRA ;
SWAN, JM .
JOURNAL OF THE CHEMICAL SOCIETY, 1950, :1947-1954
[7]   STRUCTURAL STUDIES ON PENICILLIN DERIVATIVES .4. A NOVEL REARRANGEMENT OF PENICILLIN-V SULFOXIDE [J].
COOPER, RDG ;
JOSE, FL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (08) :2575-+
[8]  
ELKS J, 1977, RECENT ADV CHEM BETA, P68
[9]  
FIESER LF, 1967, REAGENTS ORGANIC SYN, V1, P446
[10]   TOTAL SYNTHESIS OF BETA-LACTAM ANTIBIOTICS .4. EPIMERIZATION OF 6(7)-AMINOPENICILLINS AND 6(7)-CEPHALOSPORINS FROM ALPHA TO BETA [J].
FIRESTONE, RA ;
MACIEJEWICZ, NS ;
RATCLIFFE, RW ;
CHRISTENSEN, BG .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (04) :437-440