ASYMMETRIC-SYNTHESIS OF (3S)-2,3,4,5-TETRAHYDROPYRIDAZINE-3-CARBOXYLIC ACID

被引:43
作者
ASPINALL, IH
COWLEY, PM
MITCHELL, G
STOODLEY, RJ
机构
[1] UMIST,DEPT CHEM,POB 88,MANCHESTER M60 1QD,ENGLAND
[2] ZENECA AGROCHEM,JEALOTTS HILL RES STN,BRACKNELL RG12 6EY,BERKS,ENGLAND
关键词
D O I
10.1039/c39930001179
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The title compound 1a is prepared by a two-step sequence from the cycloadduct 5d, derived from di(tert-butyl) azodicarboxylate and the diene 4b by a hetero Diels-Alder reaction.
引用
收藏
页码:1179 / 1180
页数:2
相关论文
共 16 条
[1]   ASYMMETRIC DIELS-ALDER REACTIONS .5. INFLUENCE OF SUGAR SUBSTITUENTS UPON THE DIASTEREOFACIAL REACTIVITY OF (E)-3-(TERT-BUTYLDIMETHYLSILOXY)-1-(D-GLUCOPYRANOSYLOXY)BUTA-1,3-DIENES [J].
BEAGLEY, B ;
LARSEN, DS ;
PRITCHARD, RG ;
STOODLEY, RJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :3113-3127
[2]  
BOGER DL, 1987, HETERO DIELSALDER ME
[3]   ASYMMETRIC DIELS-ALDER REACTIONS .1. DIASTEREOFACIAL REACTIVITY OF (E)-3-TRIMETHYLSILYLOXYBUTA-1,3-DIENYL 2,3,4,6-TETRA-0-ACETYL-BETA-D-GLUCOPYRANOSIDE TOWARDS CYCLIC DIENOPHILES [J].
GUPTA, RC ;
RAYNOR, CM ;
STOODLEY, RJ ;
SLAWIN, AMZ ;
WILLIAMS, DJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07) :1773-1785
[4]   ASYMMETRIC DIELS-ALDER REACTIONS .2. A MODEL TO ACCOUNT FOR THE DIASTEREOFACIAL REACTIVITY OF (E)-1-(2',3',4',6'-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYLOXY)-3-TRIMETHYLSILOXYBUTA-1,3-DIENE AND ITS 2-METHYL DERIVATIVE - X-RAY MOLECULAR-STRUCTURE OF (E)-1-(2',3',4',6'-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYLOXY)-3-TRIMETHYLSILOXYBUTA-1,3-DIENE AND OF (1R,6R,9R,10S)-9-METHYL-10-(2',3',4',6'-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYLOXY)BICYCLO[4.4.0]DEC-3-ENE-2,5,8-TRIONEC [J].
GUPTA, RC ;
LARSEN, DS ;
STOODLEY, RJ ;
SLAWIN, AMZ ;
WILLIAMS, DJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (04) :739-749
[5]   AZINOTHRICIN SYNTHETIC STUDIES .1. EFFICIENT ASYMMETRIC SYNTHESES OF (3R)-PIPERAZIC AND (3S)-PIPERAZIC ACIDS [J].
HALE, KJ ;
DELISSER, VM ;
MANAVIAZAR, S .
TETRAHEDRON LETTERS, 1992, 33 (49) :7613-7616
[6]   AMINO-ACIDS AND PEPTIDES .21. SYNTHESIS OF A CONGENER OF THE CYCLOHEXADEPSIPEPTIDE ANTIBIOTIC, MONAMYCIN [J].
HASSALL, CH ;
JOHNSON, WH ;
THEOBALD, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06) :1451-1454
[7]   ASYMMETRIC DIELS-ALDER REACTIONS .4. INFLUENCE OF ANOMERIC CONFIGURATION AND 2'-O-BENZYL AND 6'-O-BENZYL SUBSTITUTION ON THE DIASTEREOFACIAL REACTIVITY OF (E)-3-(TERT-BUTYLDIMETHYLSILOXY)-1-(2',3',4',6'-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYLOXY)-BUTA-1,3-DIENE [J].
LARSEN, DS ;
STOODLEY, RJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (05) :1339-1352
[8]   ASYMMETRIC DIELS-ALDER REACTIONS .3. INFLUENCE OF BUTADIENE STRUCTURE UPON THE DIASTEREOFACIAL REACTIVITY OF (E)-1-(2',3',4',6'-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYLOXY)BUTA-1,3-DIENES [J].
LARSEN, DS ;
STOODLEY, RJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (10) :1841-1852
[9]   AQUEOUS CYCLOADDITIONS USING GLYCO-ORGANIC SUBSTRATES .1. STEREOCHEMICAL COURSE OF THE REACTION [J].
LUBINEAU, A ;
QUENEAU, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) :1001-1007
[10]   MINOR CONGENERS OF ANTRIMYCIN - APPLICATION OF SECONDARY ION MASS-SPECTROMETRY (SIMS) TO STRUCTURE DETERMINATION [J].
MORIMOTO, K ;
SHIMADA, N ;
NAGANAWA, H ;
TAKITA, T ;
UMEZAWA, H ;
KAMBARA, H .
JOURNAL OF ANTIBIOTICS, 1982, 35 (03) :378-380