An Efficient Three-Component Synthesis of 3-(5-Alkyl/aryl-1,3,4-oxadiazol-2-yl)-3-hydroxy-1,3-dihydro-2H-indol-2-ones

被引:17
作者
Adib, Mehdi [1 ]
Sheikhi, Ehsan [1 ]
Kavoosi, Azadeh [1 ]
Bijanzadeh, Hamid Reza [2 ]
机构
[1] Univ Tehran, Univ Coll Sci, Sch Chem, Tehran, Iran
[2] Tarbiat Modares Univ, Dept Chem, Tehran, Iran
来源
SYNTHESIS-STUTTGART | 2010年 / 23期
关键词
N-isocyaniminotriphenylphosphorane; isatins; carboxylic acids; 1,3,4-oxadiazoles; multi-component reactions; heterocycles; cyclizations; MULTICOMPONENT REACTIONS; ACID-DERIVATIVES; ONE-POT; (N-ISOCYANIMINO)TRIPHENYLPHOSPHORANE; POLY(AMINE-1,3,4-OXADIAZOLE)S; ISOCYANIDES; AMINO;
D O I
10.1055/s-0030-1258300
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学];
摘要
An efficient three-component synthesis of 3-(1,3,4-oxadiazol-2-yl)-3-hydroxy-1,3-dihydro-2H-indol-2-ones is described. A mixture of N-isocyaniminotriphenylphosphorane, an isatin, and a carboxylic acid undergoes a 1:1:1 addition reaction under mild conditions to afford the title compounds in excellent yields.
引用
收藏
页码:4082 / 4086
页数:5
相关论文
共 38 条
[1]
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
[2]
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) :3289-3294
[3]
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
[4]
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
[5]
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
[6]
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
[7]
Reaction between isocyanides and nitrostyrenes in water: a novel and efficient synthesis of 5-(alkylamino)-4-aryl-3-isoxazolecarboxamides [J].
Adib, Mehdi ;
Mahdavi, Mohammad ;
Ansari, Samira ;
Malihi, Farzad ;
Zhu, Long-Guan ;
Bijanzadeh, Hamid Reza .
TETRAHEDRON LETTERS, 2009, 50 (52) :7246-7248
[8]
Reaction between N-Isocyaniminotriphenylphosphorane, Aldehydes, and Carboxylic Acids: A One-Pot and Three-Component Synthesis of 2-Aryl-5-hydroxyalkyl-1,3,4-oxadiazoles [J].
Adib, Mehdi ;
Kesheh, Mahdi Riazati ;
Ansari, Samira ;
Bijanzadeh, Hamid Reza .
SYNLETT, 2009, (10) :1575-1578
[9]
A Novel One-Pot, Three-Component Synthesis of Dialkyl 5-(Alkylamino)-1-aryl-1H-pyrazole-3,4-dicarboxylates [J].
Adib, Mehdi ;
Mohammadi, Bagher ;
Bijanzadeh, Hamid Reza .
SYNLETT, 2008, (20) :3180-3182
[10]
A novel highly selective chiral auxiliary for the asymmetric synthesis of L- and D-α-amino acid derivatives via a multicomponent Ugi reaction [J].
Basso, A ;
Banfi, L ;
Riva, R ;
Guanti, G .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :575-579