A modified Sandmeyer methodology and the synthesis of (+/-)-convolutamydine A.

被引:96
作者
Garden, SJ
Torres, JC
Ferreira, AA
Silva, RB
Pinto, AC
机构
[1] Instítute de Química, Depto. de Quím. Orgân., Univ. Federal do Rio de Janeiro, Rio de Janeiro CEP 21910-240, Ilha do Fundão
关键词
D O I
10.1016/S0040-4039(97)00140-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(+/-)-Convolutamydine A (5) has been prepared by a concise synthesis from 3,5-dibromoaniline using a modified Sandmeyer methodology. The modified Sandmeyer methodology has also been found to be beneficial for the synthesis of other alpha-isonitrosoacetanilides. The 4,6-dibromohydroxyoxindole nucleus was further confirmed by comparison with the isomeric 5, 7-dibromohydraxyoxindole. (C) 1997 Elsevier Science Ltd.
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页码:1501 / 1504
页数:4
相关论文
共 15 条
[1]  
[Anonymous], 1931, J AM CHEM SOC, DOI [DOI 10.1021/JA01352A046, 10.1021/ja01352a046]
[2]   AN ANTIMALARIAL ALKALOID FROM HYDRANGEA .15. SYNTHESIS OF 5-DERIVATIVES, 6-DERIVATIVES, 7-DERIVATIVES, AND 8-DERIVATIVES WITH 2 IDENTICAL SUBSTITUENTS [J].
BAKER, BR ;
SCHAUB, RE ;
JOSEPH, JP ;
MCEVOY, FJ ;
WILLIAMS, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1952, 17 (01) :149-156
[3]  
Billica HR, 1955, ORG SYNTH, V3, P176
[4]   Condensations of isatm with acetone by the Knoevenagel method [J].
Braude, F ;
Lindwall, HG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1933, 55 :325-327
[5]   THE BENZIDINE REARRANGEMENT .2. THE REARRANGEMENTS OF 3 3,3',5,5'-TETRASUBSTITUTED HYDRAZOBENZENES IN 2 1 SULFURIC ACID [J].
CARLIN, RB ;
FORSHEY, WO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (02) :793-801
[6]   CINNOLINE CHEMISTRY .12. SYNTHESIS OF 6-FLUORO-4-METHYLCINNOLINE AND OTHER CINNOLINES AS POTENTIAL ANTITUMOR AGENTS [J].
CASTLE, RN ;
ADACHI, K ;
GUITHER, WD .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1965, 2 (04) :459-&
[7]   Nickel by the Raney process as a catalyst of hydrogenation [J].
Covert, LW ;
Adkins, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1932, 54 :4116-4117
[8]  
GAULIN CA, 1951, J AM CHEM SOC, V753, P3579
[9]   CONVOLUTAMYDINE-A, A NOVEL BIOACTIVE HYDROXYOXINDOLE ALKALOID FROM MARINE BRYOZOAN AMATHIA-CONVOLUTA [J].
KAMANO, Y ;
ZHANG, HP ;
ICHIHARA, Y ;
KIZU, H ;
KOMIYAMA, K ;
PETTIT, GR .
TETRAHEDRON LETTERS, 1995, 36 (16) :2783-2784
[10]  
Marvel CS., 1941, Org Synth, V1, P327