A new modification of the Passerini reaction: a one-pot synthesis of α-acyloxyamides via sequential Kornblum cocidation/Passerini reaction

被引：12
作者：
Adib, Mehdi [1 ]
Sheikhi, Ehsan [1 ]
Azimzadeh, Marjan [1 ]
机构：
[1] Univ Tehran, Coll Sci, Sch Chem, Tehran, Iran
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 15期
关键词：
Kornblum oxidation; Passerini reaction; alpha-Acyloxyamides; Benzylic substrates; Dimethyl sulfoxide; Isocyanides; MULTICOMPONENT REACTIONS; SELECTIVE METHOD; ALKYL-HALIDES; ISOCYANIDES; OXIDATION; AMINES;
D O I：
10.1016/j.tetlet.2015.02.007
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel approach for the synthesis of alpha-acyloxyamides is described. Benzylic substrates (halides or tosylates), under mild Kornblum conditions, are oxidized to give the corresponding aldehydes, which undergo a Passerini reaction with carboxylic acids and isocyanides to produce the corresponding alpha-acyloxyamides in excellent yields. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1933 / 1936
页数：4
相关论文
共 45 条
[1]   One-Pot Four-Component Synthesis of N2-Alkyl-N3-[2-(1,3,4-oxadiazol-2-yl)aryl]benzofuran-2,3-diamines [J].
Adib, Mehdi ;
Sheikhi, Ehsan ;
Karimzadeh, Morteza ;
Bijanzadeh, Hamid Reza ;
Amanlou, Massoud .
HELVETICA CHIMICA ACTA, 2012, 95 (05) :788-794
[2]   Microwave-assisted reaction between 2-aminobenzoic acids, 2-hydroxybenzaldehydes, and arylboronic acids: a one-pot three-component synthesis of bridgehead bicyclo[4.4.0]boron heterocycles [J].
Adib, Mehdi ;
Sheikhi, Ehsan ;
Bijanzadeh, Hamid Reza ;
Zhu, Long-Guan .
TETRAHEDRON, 2012, 68 (16) :3377-3383
[3]   Solvent-free and three-component synthesis of 1H,6H-6λ5-[1,2]benzoxaphospholo[2,3-b][1,2]benzoxaphosphol-1-ones [J].
Adib, Mehdi ;
Sheikhi, Ehsan ;
Bagheri, Mehdi ;
Bijanzadeh, Hamid Reza ;
Amanlou, Masoud .
TETRAHEDRON, 2012, 68 (15) :3237-3242
[4]   Reaction between triphenylphosphine and aromatic amines in the presence of diethyl azodicarboxylate: an efficient synthesis of aryliminophosphoranes under neutral and mild conditions [J].
Adib, Mehdi ;
Sheikhi, Ehsan ;
Deljoush, Azadeh .
TETRAHEDRON, 2011, 67 (22) :4137-4140
[5]   Solvent-Free Reaction between Anthranilic Acids and Isocyanides: A Novel Approach for the Synthesis of 2-Unsubstituted 4(3H)-Quinazolinones [J].
Adib, Mehdi ;
Karimzadeh, Morteza ;
Mahdavi, Mohammad ;
Sheikhi, Ehsan ;
Mirzaei, Peiman .
SYNLETT, 2011, (06) :834-836
[6]   Revisiting the Passerini reaction under eco-friendly reaction conditions [J].
Andrade, Carlos Kleber Z. ;
Takada, Sayuri Cristina S. ;
Suarez, Paulo Anselmo Z. ;
Alves, Melquizedeque B. .
SYNLETT, 2006, (10) :1539-1542
[7]   Stereochemical control of the Passerini reaction [J].
Andreana, PR ;
Liu, CC ;
Schreiber, SL .
ORGANIC LETTERS, 2004, 6 (23) :4231-4233
[8]   THE APPLICATION OF THE PASSERINI REACTION TO STEROID KETONES [J].
BAKER, RH ;
SCHLESINGER, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1945, 67 (09) :1499-1500
[9]   Fast and efficient solvent-free Passerini reaction [J].
Bousquet, Till ;
Jida, Mouhamad ;
Soueidan, Mohamad ;
Deprez-Poulain, Rebecca ;
Agbossou-Niedercorn, Francine ;
Pelinski, Lydie .
TETRAHEDRON LETTERS, 2012, 53 (03) :306-308
[10]  
Bratulescu G, 2010, REV CHIM-BUCHAREST, V61, P815
12345