One-Pot Four-Component Synthesis of N2-Alkyl-N3-[2-(1,3,4-oxadiazol-2-yl)aryl]benzofuran-2,3-diamines

被引:11
作者
Adib, Mehdi [1 ]
Sheikhi, Ehsan [1 ]
Karimzadeh, Morteza [1 ]
Bijanzadeh, Hamid Reza [2 ]
Amanlou, Massoud [3 ,4 ]
机构
[1] Univ Tehran, Sch Chem, Univ Coll Sci, Tehran, Iran
[2] Tarbiat Modares Univ, Dept Chem, Tehran, Iran
[3] Univ Tehran Med Sci, Pharmaceut Sci Res Ctr, Tehran, Iran
[4] Univ Tehran Med Sci, Dept Med Chem, Tehran, Iran
关键词
Benzofuran-2; 3-diamines; Multicomponent reactions; PALLADIUM-CATALYZED HETEROANNULATION; SOLID-PHASE SYNTHESIS; SUR LE BENZOFURANNE; MULTICOMPONENT REACTIONS; 3-COMPONENT REACTION; EFFICIENT SYNTHESIS; COUPLING REACTIONS; FURAN-DERIVATIVES; CASCADE REACTIONS; ACID-DERIVATIVES;
D O I
10.1002/hlca.201100403
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple synthesis of N2-alkyl-N3-[2-(1,3,4-oxadiazol-2-yl)aryl]benzofuran-2,3-diamines 5 via a one-pot four-component reaction is described (Scheme 1). A mixture of N-(isocyanoimino)triphenylphosphorane (1), a 2-aminobenzoic acid 2, a 2-hydroxybenzaldehyde 3, and an isocyanide 4 in absolute EtOH at room temperature undergoes a smooth reaction to afford 5 in excellent yields (Table).
引用
收藏
页码:788 / 794
页数:7
相关论文
共 74 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]   QUINONE IMIDES .39. ADDUCTS OF QUINONE MONOIMIDES AND CONVERSION OF ACTIVE METHYLENE ADDUCTS TO BENZOFURANS [J].
ADAMS, R ;
WHITAKER, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (03) :658-663
[3]   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
[4]   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
[5]   Reaction between N-Isocyaniminotriphenylphosphorane, Aldimines, Meldrum's Acid and Water: Diastereoselective Synthesis of 3,4-Disubstituted N-Aminopyrrolidine-2,5-diones [J].
Adib, Mehdi ;
Ansari, Samira ;
Bijanzadeh, Hamid Reza .
SYNLETT, 2011, (05) :619-622
[6]   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 [J].
Adib, Mehdi ;
Sheikhi, Ehsan ;
Kavoosi, Azadeh ;
Bijanzadeh, Hamid Reza .
SYNTHESIS-STUTTGART, 2010, (23) :4082-4086
[7]   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
[8]   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
[9]   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
[10]   A One-Pot, Four-Component Synthesis of N-Substituted 2,4-Diarylimidazoles [J].
Adib, Mehdi ;
Ansari, Samira ;
Feizi, Shahzad ;
Damavandi, Jafar Asgarian ;
Mirzaei, Peiman .
SYNLETT, 2009, (20) :3263-3266