A Simple Method for the Synthesis of 3-Arylthieno[2,3-b]pyridines via Iodine-Mediated Cyclization of 3-(1-Arylalkenyl)-2-[(1-phenylethyl)sulfanyl]pyridines

被引:7
作者
Kobayashi, Kazuhiro [1 ]
Nakamura, Daizo [1 ]
Shiroyama, Yasuhiko [1 ]
Fukamachi, Shuhei [1 ]
Konishi, Hisatoshi [1 ]
机构
[1] Tottori Univ, Grad Sch Engn, Dept Chem & Biotechnol, Div Appl Chem, Tottori 6808552, Japan
来源
SYNTHESIS-STUTTGART | 2009年 / 13期
关键词
thieno[2,3-b]pyridines; iodine; 2-bromopyridines; cyclization; heterocycles; PYRIDINE; THIENOPYRIDINE; DERIVATIVES; AGENTS;
D O I
10.1055/s-0029-1216857
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Arylthieno[2,3-b]pyridines are synthesized in a short four-step sequence from readily available 2-bromopyridines. The final and key step of the reported method involves an iodine-mediated 5-endo cyclization of 3-(1-arylalkenyl)-2-[(1-phenylethyl)sulfanyl]pyridines.
引用
收藏
页码:2179 / 2183
页数:5
相关论文
共 19 条
[1]   Reactions with hydrazonoyl halides 45:: Synthesis of some new triazolino[4,3-a]pyrimidines, pyrazolo[3,4-d]pyridazines, isoxazolo[3,4-d]pyridazines, and thieno[2,3-b]pyridines [J].
Abdelhamid, AO ;
Al-Atoom, AA .
SYNTHETIC COMMUNICATIONS, 2006, 36 (01) :97-110
[2]   Studies with S-alkylpyrimidine:: New route for the synthesis derivatives of isoxazol, pyrazolo[1,5-a]pyrimidine, pyridazine, pyridine, thieno[2,3-b]pyridine and thiophene of potential anti-HIV [J].
Al-Omran, Fatima A. ;
El-Khair, Adel A. .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (04) :1057-1063
[3]   Synthesis and antidiabetic activity of 2,5-disubstituted-3-imidazol-2-yl-pyrrolo[2,3-b]pyridines and thieno[2,3-b]pyridines [J].
Bahekar, Rajesh H. ;
Jain, Mukul R. ;
Jadav, Pradip A. ;
Prajapati, Vijay M. ;
Patel, Dipam N. ;
Gupta, Arun A. ;
Sharma, Ajay ;
Tom, Robby ;
Bandyopadhya, Debdutta ;
Modi, Honey ;
Patel, Pankaj R. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (21) :6782-6795
[4]  
Bernardino AMR, 2004, HETEROCYCL COMMUN, V10, P407
[5]   Identification of 7-phenylaxaminothieno[3,2-b]pyridine-6-carbonitriles as a new class of Src kinase inhibitors [J].
Boschelli, DH ;
Wu, BQ ;
Sosa, ACB ;
Durutlic, H ;
Ye, F ;
Raifeld, Y ;
Golas, JM ;
Boschelli, F .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (27) :6666-6668
[6]   Synthesis and PKCθ inhibitory activity of a series of 4-(indol-5-ylamino)thieno[2,3-b]pyridine-5-carbonitriles [J].
Boschelli, Diane H. ;
Wu, Biqi ;
Sosa, Ana Carolina Barrios ;
Chen, Joan ;
Asselin, Magda ;
Cole, Derek C. ;
Lee, Julie ;
Yang, Xiaoke ;
Chaudhary, Divya .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (09) :2850-2853
[7]   Thienopyridine and benzofuran derivatives as potent anti-tumor agents possessing different structure-activity relationships [J].
Hayakawa, I ;
Shioya, R ;
Agatsuma, T ;
Furukawa, H ;
Sugano, Y .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (13) :3411-3414
[8]   Dutch resolution: Separation of enantiomers with families of resolving agents. A status report [J].
Kellogg, RM ;
Nieuwenhuijzen, JW ;
Pouwer, K ;
Vries, TR ;
Broxterman, QB ;
Grimbergen, RFP ;
Kaptein, B ;
La Crois, RM ;
de Wever, E ;
Zwaagstra, K ;
van der Laan, AC .
SYNTHESIS-STUTTGART, 2003, (10) :1626-1638
[9]   Convenient synthesis of 3-substituted benzo[b]thiophenes by iodine-mediated cyclization of α-substituted 2-(1-Phenylethylthio)styrenes [J].
Kobayashi, Kazuhiro ;
Nakamura, Daizo ;
Miyamoto, Kazuna ;
Morikawa, Osamu ;
Konishi, Hisatoshi .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2007, 80 (09) :1780-1784
[10]   Antibacterial profile against drug-resistant Staphylococcus epidermidis clinical strain and structure-activity relationship studies of 1H-pyrazolo[3,4-b]pyridine and thieno[2,3-b]pyridine derivatives [J].
Leal, Bruno ;
Afonso, Ilidio F. ;
Rodrigues, Carlos R. ;
Abreu, Paula A. ;
Garrett, Rafael ;
Pinheiro, Luiz Carlos S. ;
Azevedo, Alexandre R. ;
Borges, Julio C. ;
Vegi, Percilene F. ;
Santos, Claudio C. C. ;
da Silveira, Francisco C. A. ;
Cabral, Lucio M. ;
Frugulhetti, Izabel C. P. P. ;
Bernardino, Alice M. R. ;
Santos, Dilvani O. ;
Castro, Helena C. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (17) :8196-8204