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

被引：19
作者：
Adib, Mehdi [1 ]
Sheikhi, Ehsan [1 ]
Bijanzadeh, Hamid Reza [2 ]
Zhu, Long-Guan [3 ]
机构：
[1] Univ Tehran, Univ Coll Sci, Sch Chem, Tehran, Iran
[2] Tarbiat Modares Univ, Dept Chem, Tehran, Iran
[3] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
来源：
TETRAHEDRON | 2012年 / 68卷 / 16期
关键词：
2-Aminobenzoic acids; 2-Hydroxybenzaldehydes; Arylboronic acids; Bridgehead bicyclo[4.4.0]boron heterocycles; X-RAY-DIFFRACTION; MULTICOMPONENT REACTIONS; SPECTROSCOPIC METHODS; ASYMMETRIC-SYNTHESIS; OPTICAL-PROPERTIES; ALPHA-AMINO; BORON; ESTERS; NITROGEN; DERIVATIVES;
D O I：
10.1016/j.tet.2012.02.030
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A one-pot three-component synthesis of 6-aryl-8H-dibenzo[d,h][1,3,7,2]dioxazaborecin-8-ones is described. A mixture of 2-aminobenzoic acid, 2-hydroxybenzaldehyde, and arylboronic acid undergo a 1:1:1 addition reaction in CCl4 under microwave irradiation to produce bridgehead bicyclo[4.4.0]boron heterocycles in excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3377 / 3383
页数：7
相关论文
共 59 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]   Synthesis and characterization of boronates derived from non-symmetric amino-bis-phenols [J].
Abreu, A ;
Alas, SJ ;
Beltrán, HI ;
Santillan, R ;
Farfán, N .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (03) :337-348
[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) :3289-3294
[4]   An efficient synthesis of 3-amino-2-arylimidazo[1,2-a]pyridines [J].
Adib, Mehdi ;
Sheibani, Esmail ;
Zhu, Long-Guan ;
Mirzaei, Peiman .
TETRAHEDRON LETTERS, 2008, 49 (34) :5108-5110
[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]   Synthesis of 2-(alkylamino)-5-{alkyl[(2-oxo-2H-chromen-3-yl)carbonyl]amino}-3,4-furandicarboxylates using a multi-component reaction in water [J].
Adib, Mehdi ;
Sheikhi, Ehsan ;
Kavoosi, Azadeh ;
Bijanzadeh, Hamid Reza .
TETRAHEDRON, 2010, 66 (47) :9263-9269
[8]   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
[9]   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
[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
123456