Reaction between triphenylphosphine and aromatic amines in the presence of diethyl azodicarboxylate: an efficient synthesis of aryliminophosphoranes under neutral and mild conditions

被引:15
作者
Adib, Mehdi [1 ]
Sheikhi, Ehsan [1 ]
Deljoush, Azadeh [1 ]
机构
[1] Univ Tehran, Univ Coll Sci, Sch Chem, Tehran, Iran
关键词
Aryliminophosphoranes; Triphenylphosphine; Diethyl azodicarboxylate; Mitsonobu reaction; AZA-WITTIG REACTION; ONE-POT; HUISGEN ZWITTERION; MITSUNOBU REACTION; CARBONYL-COMPOUNDS; DERIVATIVES; PHOSPHINE; ACID; DIARYL-1,2-DIONES; IMINOPHOSPHORANES;
D O I
10.1016/j.tet.2011.03.097
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of aryliminophosphoranes is described. A mixture of an aromatic amine, diethyl azodicarboxylate and triphenylphosphine undergo a Mitsonobu type reaction at ambient temperature in dry dichloromethane to afford aryliminophosphoranes in excellent yields. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4137 / 4140
页数:4
相关论文
共 58 条
[1]   THE CHEMISTRY OF PHOSPHINIMINES [J].
ABEL, EW ;
MUCKLEJOHN, SA .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1981, 9 (03) :235-266
[2]   A new, one-pot, multi-component synthesis of imines of 3-amino-2-arylimidazo[1,2-a]pyridines, 3-amino-2-arylimidazo[1,2-a]pyrazines, and 3-amino-2-arylimidazo[1,2-a]pyrimidines [J].
Abid, Mehdi ;
Sheibani, Esmail ;
Bijanzadeh, Hamid Reza ;
Zhu, Long-Guan .
TETRAHEDRON, 2008, 64 (47) :10681-10686
[3]   Vinyltriphenylphosphonium salt-mediated efficient synthesis of iminophosphoranes derived from 2-aminothiazoles [J].
Adib, M ;
Mostofi, M ;
Ghanbary, K ;
Bijanzadeh, HR .
SYNTHESIS-STUTTGART, 2005, (10) :1663-1667
[4]   A Novel, One-Pot, Efficient Synthesis of 2-Aroyl-1,4-diaryl-7,9-dimethyl-7,9-diazaspiro[4.5]deca-1,3-diene-6,8,10-triones [J].
Adib, Mehdi ;
Sayahi, Mohammad Hosein ;
Ziyadi, Hakimeh ;
Zhu, Long-Guan ;
Bijanzadeh, Hamid Reza .
SYNTHESIS-STUTTGART, 2008, 20 (20) :3289-3294
[5]   A novel and simple synthesis of 9H-Pyrimido[4,5-b]indoles under microwave irradiation and solvent-free conditions [J].
Adib, Mehdi ;
Mohammadi, Bagher ;
Bijanzadeh, Hamid Reza .
SYNLETT, 2008, (02) :177-180
[6]   A new, one-pot, three-component synthesis of 4H-pyrido[1,2-a]-pyrimidines, 4H-pyrimido[1,2-a]pyrimidines, and 4H-pyrazino[ 1,2-a] pyrimidines [J].
Adib, Mehdi ;
Sayahi, Mohammad Hosein ;
Ziyadi, Hakimeh ;
Bijanzadeh, Hamid Reza ;
Zhu, Long-Guan .
TETRAHEDRON, 2007, 63 (45) :11135-11140
[7]   Microwave-Assisted, One-Pot Reaction of Pyridines, α-Bromoketones and Ammonium Acetate: An Efficient and Simple Synthesis of Imidazo[1,2-a]-pyridines [J].
Adib, Mehdi ;
Mohamadi, Ali ;
Sheikhi, Ehsan ;
Ansari, Samira ;
Bijanzadeh, Hamid Reza .
SYNLETT, 2010, (11) :1606-1608
[8]   A multi-component synthesis of 3-aryl-1-(arylmethylideneamino) pyrrolidine-2,5-diones [J].
Adib, Mehdi ;
Ansari, Samira ;
Fatemi, Solmaz ;
Bijanzadeh, Hamid Reza ;
Zhu, Long-Guan .
TETRAHEDRON, 2010, 66 (14) :2723-2727
[9]   An Efficient Three-Component Synthesis of 3-(1-Hydroxyalkyl)[1,2,4]-triazolo[4,3-c]quinazolines [J].
Adib, Mehdi ;
Ansari, Samira ;
Feizi, Shahzad ;
Bijanzadeh, Hamid Reza .
SYNLETT, 2010, (06) :921-923
[10]   A novel, one-pot, solvent-, and catalyst-free synthesis of 2-aryl/alkyl-4(3H)-quinazolinones [J].
Adib, Mehdi ;
Ansari, Samira ;
Mohammadi, Ali ;
Bijanzadeh, Hamid Reza .
TETRAHEDRON LETTERS, 2010, 51 (01) :30-32