First Acid-Catalyzed Entry to O-Alkylated Hydroximides from Benzylic Alcohols

被引:19
作者
Reddy, Chada Raji [1 ]
Radhika, Laghuvarapu [1 ]
Kumar, Togapur Pavan [1 ]
Chandrasekhar, Srivari [1 ]
机构
[1] Indian Inst Chem Technol, Organ Chem Div NPL 1, Hyderabad 500607, Andhra Pradesh, India
关键词
Alkylation; Acid catalysis; Heterocycles; Alcohols; CHIRAL ALPHA-(AMINOOXY)ARYLACETIC ESTER; NUCLEOPHILIC-SUBSTITUTION; PROPARGYLIC ALCOHOLS; AMINOXY ACIDS; OXIME ETHERS; PEPTIDES; DERIVATIVES; ROUTE; TRANSFORMATION; EFFICIENT;
D O I
10.1002/ejoc.201100797
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile method for the synthesis of O-alkylated hydroximides through the acid-catalyzed alkylation of hydroximides by using benzylic alcohols as alkylating agents is described for the first time. The obtained O-propargylated products offered easy access to 2,5-and 4,5-dihydroisoxazoles.
引用
收藏
页码:5967 / 5970
页数:4
相关论文
共 53 条
[11]   Direct Nucleophilic SN1-Type Reactions of Alcohols [J].
Emer, Enrico ;
Sinisi, Riccardo ;
Capdevila, Montse Guiteras ;
Petruzziello, Diego ;
De Vincentiis, Francesco ;
Cozzi, Pier Giorgio .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (04) :647-666
[12]   The Meyer-Schuster rearrangement for the synthesis of α,β-unsaturated carbonyl compounds [J].
Engel, Douglas A. ;
Dudley, Gregory B. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (20) :4149-4158
[13]   On the viability of 5-endo-dig cyclisations of O-propargylic hydroxylamine derivatives, leading to 2,5-dihydroisoxazoles (3-isoxazolines) [J].
Foot, Oliver F. ;
Knight, David W. ;
Low, Ai Cheng Lilian ;
Li, YingFa .
TETRAHEDRON LETTERS, 2007, 48 (04) :647-650
[14]   Alcohols as electrophiles in C-C bond-forming reactions:: The hydrogen autotransfer process [J].
Guillena, Gabriela ;
Ramon, Diego J. ;
Yus, Miguel .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) :2358-2364
[15]   Hydrogen Autotransfer in the N-Alkylation of Amines and Related Compounds using Alcohols and Amines as Electrophiles [J].
Guillena, Gabriela ;
Ramon, Diego J. ;
Yus, Miguel .
CHEMICAL REVIEWS, 2010, 110 (03) :1611-1641
[16]   Discovery of novel and potent benzhydryl-tropane trypanocides highly selective for Trypanosoma cruzi [J].
Holloway, G. A. ;
Parisot, J. P. ;
Novello, P. M. ;
Watson, K. G. ;
Armstrong, T. ;
Thompson, R. C. A. ;
Street, I. P. ;
Baell, J. B. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (06) :1816-1818
[17]  
Hughes D.L., 1992, ORG REACT, V42, P335, DOI DOI 10.1002/0471264180.0R042.02
[18]   SYNTHESIS OF A CHIRAL ALPHA-(AMINOOXY)ARYLACETIC ESTER .1. A ROUTE THROUGH OPTICAL RESOLUTION OF A RACEMIC ALPHA-(PHTHALIMIDOOXY)ARYLACETIC ACID [J].
IWAGAMI, H ;
NAKAZAWA, M ;
YATAGAI, M ;
HIJIYA, T ;
HONDA, Y ;
NAORA, H ;
OHNUKI, T ;
YUKAWA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (11) :3073-3081
[19]   SYNTHESIS OF A CHIRAL ALPHA-(AMINOOXY)ARYLACETIC ESTER .2. A ROUTE THROUGH A CHIRAL 2-HYDROXY-2-PHENYLACETIC ACID-DERIVATIVE [J].
IWAGAMI, H ;
YATAGAI, M ;
NAKAZAWA, M ;
ORITA, H ;
HONDA, Y ;
OHNUKI, T ;
YUKAWA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1991, 64 (01) :175-182
[20]   Optimized synthesis of aminooxy-peptides as glycoprobe precursors for surface-based sugar-protein interaction studies [J].
Jimenez-Castells, Carmen ;
de la Torre, Beatriz G. ;
Gallego, Ricardo Gutierrez ;
Andreu, David .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (18) :5155-5158