An Efficient Aromatization of 2-Amino-4,5,6,7-tetrahydrobenzo-[b]thiophene-3-carboxylates in Dimethyl Sulfoxide Catalyzed by p-Toluenesulfonic Acid

被引：21
作者：
Adib, Mehdi [1 ]
Soheilizad, Mehd [1 ]
Rajai-daryasaraei, Saideh [1 ]
Mirzaei, Peiman [2 ]
机构：
[1] Univ Tehran, Coll Sci, Sch Chem, Tehran, Iran
[2] Shahid Beheshti Univ, Dept Chem, Tehran, Iran
来源：
SYNLETT | 2015年 / 26卷 / 08期
关键词：
2-aminobenzo[b]thiophene-3-carboxylates; Gewald reaction; oxidation-aromatization; dimethyl sulfoxide; p-toluenesulfonic acid; ESTROGEN-RECEPTOR MODULATORS; BIOLOGICAL EVALUATION; BENZOTHIOPHENE; DERIVATIVES; LIGANDS; ARZOXIFENE; INHIBITORS; THIOPHENE; AGENTS;
D O I：
10.1055/s-0034-1379998
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel oxidation-aromatization of alkyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylates is reported. The Gewald product, obtained from three-component condensation reaction between a cyclohexanone, an alkyl cyanoacetate, and sulfur, underwent an oxidation reaction in dimethyl sulfoxide in the presence of a catalytic amount of p-toluenesulfonic acid to give the corresponding alkyl 2-aminobenzo[b]thiophene-3-carboxylate in excellent yield.
引用
收藏
页码：1101 / 1105
页数：5
相关论文
共 44 条
[1]   Synthesis of pure stereoisomers of benzo[b]thienyl dehydrophenylalanines by Suzuki cross-coupling.: Preliminary studies of antimicrobial activity [J].
Abreu, AS ;
Ferreira, PMT ;
Monteiro, LS ;
Queiroz, MJRP ;
Ferreira, ICFR ;
Calhelha, RC ;
Estevinho, LM .
TETRAHEDRON, 2004, 60 (51) :11821-11828
[2]   A Simple Synthesis of Alkyl 2-Aminobenzo[b]thiophene-3-carboxylates via an Unexpected Dehydrogenation of Alkyl 2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylates [J].
Adib, Mehdi ;
Bayanati, Maryam ;
Soheilizad, Mehdi ;
Ghazvini, Helia Janatian ;
Tajbakhsh, Mahmood ;
Amanlou, Massoud .
SYNLETT, 2014, 25 (20) :2918-2922
[3]   A highly diastereoselective five-component synthesis of 1-(alkylimino)-5,5-dicyano-3a-aryloctahydro-3-oxacyclobuta[cd]pentalene-1a,2,5a,5b(2H,3aH)-tetracarboxylates [J].
Adib, Mehdi ;
Sheikhi, Ehsan ;
Haghshenas, Pouyan ;
Rajai-Daryasarei, Saideh ;
Bijanzadeh, Hamid Reza ;
Zhu, Long-Guan .
TETRAHEDRON LETTERS, 2014, 55 (36) :4983-4986
[4]   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
[5]   One-pot synthesis of imidazo[1,2-a]pyridines from benzyl halides or benzyl tosylates, 2-aminopyridines and isocyanides [J].
Adib, Mehdi ;
Sheikhi, Ehsan ;
Rezaei, Narjes .
TETRAHEDRON LETTERS, 2011, 52 (25) :3191-3194
[6]   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
[7]   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
[8]  
Arndt H.D., 2006, ANGEW CHEM, V118, P4664
[9]   ANTAGONISM OF ESTROGEN ACTION WITH A NEW BENZOTHIOPHENE DERIVED ANTI-ESTROGEN [J].
BLACK, LJ ;
JONES, CD ;
FALCONE, JF .
LIFE SCIENCES, 1983, 32 (09) :1031-1036
[10]  
Burkart S. E., 1991, US Patent, Patent No. [US5073564A, 5073564]
12345