A New One-Pot Procedure for a Ring Contraction Reaction using Iodine/H2O2

被引:19
作者
Ferreira, Sabrina B. [2 ]
Kaiser, Carlos R. [2 ]
Ferreira, Vitor F. [1 ]
机构
[1] Univ Fed Fluminense, Dept Quim Organ, Inst Quim, BR-24020141 Rio De Janeiro, Brazil
[2] Univ Fed Rio de Janeiro, Ilha Fundao, LABRMN, Inst Quim, BR-21949900 Rio De Janeiro, Brazil
关键词
ring contractions; quinones; lapachones; iodine; hydrogen peroxide;
D O I
10.1055/s-0028-1083519
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new procedure for ring contraction from 1,2-quinones using aqueous H2O2 (30%) and catalytic amount of I-2 in acetonitrile is reported.
引用
收藏
页码:2625 / 2628
页数:4
相关论文
共 29 条
[11]   Trypanocidal agents with low cytotoxicity to mammalian cell line:: A comparison of the theoretical and biological features of lapachone derivatives [J].
Ferreira, Vitor F. ;
Jorqueira, Alessandra ;
Souza, Alessandra M. T. ;
da Silva, Milton N. ;
de Souza, Maria C. B. V. ;
Gouvea, Robson M. ;
Rodrigues, Carlos R. ;
Pinto, Antonio V. ;
Castro, Helena C. ;
Santos, Dilvani O. ;
Araujo, Humberto P. ;
Bourguignon, Saulo C. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (16) :5459-5466
[12]   REMOTE AROMATIC METALATION - AN ANIONIC FRIEDEL-CRAFTS EQUIVALENT FOR THE REGIOSELECTIVE SYNTHESIS OF CONDENSED FLUORENONES FROM BIARYL AND META-TERARYL 2-AMIDES [J].
FU, JM ;
ZHAO, BP ;
SHARP, MJ ;
SNIECKUS, V .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1683-1685
[13]   A novel soluble poly(fluorenylenevinylene) conjugated polymer:: synthesis, characterization and application to optoelectronic devices [J].
Gruber, J ;
Li, RWC ;
Aguiar, LHJMC ;
Benvenho, ARV ;
Lessmann, R ;
Hümmelgen, IA .
JOURNAL OF MATERIALS CHEMISTRY, 2005, 15 (04) :517-522
[14]  
Hooker S. C., 1892, J CHEM SOC, V61, P611
[15]   Lapachol: an overview [J].
Hussain, Hidayat ;
Krohn, Karsten ;
Ahmad, Viqar Uddin ;
Miana, Ghulam Abbas ;
Green, Ivan Robert .
ARKIVOC, 2007, :145-171
[16]   Effective and selective iodofunctionalisation of organic molecules in water using the iodine-hydrogen peroxide tandem [J].
Jereb, M ;
Zupan, M ;
Stavber, S .
CHEMICAL COMMUNICATIONS, 2004, (22) :2614-2615
[17]   Oxyrane derivative of α-lapachone is potent growth inhibitor of Trypanosoma cruzi epimastigote forms [J].
Jorqueira, Alessandra ;
Gouvea, Robson M. ;
Ferreira, Vitor F. ;
da Silva, Milton N. ;
de Souza, Maria C. B. V. ;
Zuma, Aline A. ;
Cavalcanti, Danielle F. B. ;
Araujo, Humberto P. ;
Santos, Dilvani O. ;
Bourguignon, Saulo C. .
PARASITOLOGY RESEARCH, 2006, 99 (04) :429-433
[18]   Identification of the in vitro metabolites of 3,4-dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-dione(ARQ 501; β-lapachone) in whole blood [J].
Miao, Xiu-Sheng ;
Miao, Sheng ;
Song, Pengfei ;
Savage, Ronald E. ;
Zhong, Caiyun ;
Yang, Rui-Yang ;
Kizer, Darin ;
Wu, Hui ;
Volckova, Erika ;
Ashwell, Mark A. ;
Supko, Jeffrey G. ;
He, Xiaoying ;
Chan, Thomas C. K. .
DRUG METABOLISM AND DISPOSITION, 2008, 36 (04) :641-648
[19]   Regiospecific synthesis of benzo[b]fluorenones via ring contraction by benzil-benzilic acid rearrangement of benz[a]anthracene-5,6-diones [J].
Patra, Asit ;
Ghorai, Sujit K. ;
De, Saroj R. ;
Mal, Dipakranjan .
SYNTHESIS-STUTTGART, 2006, (15) :2556-2562
[20]  
Portela MPM, 1996, BIOCHEM PHARMACOL, V52, P1875