Subscribe to RSS
DOI: 10.1055/s-0034-1379011
A Convenient and Efficient Synthesis of 2-(Het)arylthieno[3,2-b]pyridin-7(4H)-ones and 2,3-Di(het)arylthieno[3,2-b]pyridin-7(4H)-ones
Publication History
Received: 01 June 2014
Accepted after revision: 01 August 2014
Publication Date:
28 August 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201424/lookinside/thumbnails/10.1055-s-0034-1379011-1.jpg)
Abstract
A simple and efficient synthesis of 2-aryl-3-hydroxythieno[3,2-b]pyridin-7(4H)-ones, 7-methoxy-2,3-diarylthieno[3,2-b]pyridines, and 2,3-diarylthieno[3,2-b]pyridin-7(4H)-ones is presented. The synthesis involves thioalkylation of methyl 4-methoxypicolinate at the 3-position, followed by cyclization in situ to give 2-aryl-7-methoxythieno[3,2-b]pyridin-3-ols. Demethylation of these compounds gives the corresponding 2-arylthieno[3,2-b]pyridin-7(4H)-ones. Further functionalization of 7-methoxy-2-arylthieno[3,2-b]pyridin-3-ols was achieved by converting the hydroxy group into the corresponding triflate, which underwent palladium-catalyzed cross-coupling to give 7-methoxy-2,3-di(het)arylthieno[3,2-b]pyridines. Subsequent demethylation of the 7-methoxy group gave the corresponding pyridinones.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
Primary Data
- for this article are available online at http:// www.thieme-connect.com/products/ejournals/journal/10.1055/s-00000084 and can be cited using the following DOI: 10.4125/pd0060th.
- Primary Data
-
References
- 1 Baker RK, Rupprecht KM, Pessolano AA, Durette PL. US 4767766, 1988
- 2 Boschelli DH, Wu B, Barrios Sosa AC, Durutlic H, Chen JJ, Wang J, Golas JM, Lucas J, Boschelli F. J. Med. Chem. 2005; 48: 3891
- 3 Munchhof MJ, Beebe JS, Casavant JM, Cooper BA, Doty JL, Hidgon RC, Hillerman SM, Soderstrom CI, Knauth EA, Marx MA, Rossi AM. K, Sobolov SB, Sun J. Bioorg. Med. Chem. Lett. 2004; 14: 21
- 4a Hayakawa I, Shioya R, Agatsuma T, Furukawa H, Sugano Y. Bioorg. Med. Chem. Lett. 2004; 14: 3411
- 4b Queiroz M.-JR. P, Calhelha RC, Vale-Silva LA, Pinto E, Nascimento MS.-J. Eur. J. Med. Chem. 2010; 45: 5732
- 4c Castanheira EM. S, Carvalho MS. D, Rodrigues AR. O, Calhelha RC, Queiroz M.-JR. P. Nanoscale Res. Lett. 2011; 6: 379
- 5 van Straten NC. R, Schoonus-Gerritsma GG, van Someren RG, Draaijer J, Adang AE. P, Timmers CM, Hanssen RG. J. M, van Boeckel CA. A. ChemBioChem 2002; 3: 1023
- 6 New JS, Christopher WL, Yevich JP, Butler R, Schlemmer RF. Jr, VanderMealen CP, Cipollina JA. J. Med. Chem. 1989; 32: 1147
- 7 Malicorne G, Bompart J, Giral L, Despaux E. Eur. J. Med. Chem. 1991; 26: 3
- 8a Wagman AS, Wentland MP In Comprehensive Medicinal Chemistry II . Taylor JB, Triggle DJ. Elsevier; Oxford: 2007
- 8b De Souza MV. N. Mini-Rev. Med. Chem. 2005; 5: 1009
- 8c Emami S, Shafiee A, Foroumadi A. Mini-Rev. Med. Chem. 2006; 6: 375
- 9 Boteva AA, Krasnykh OP. Chem. Heterocycl. Compd. (Engl. Transl.) 2009; 45: 757
- 10a Khan MA, Guarçoni AE. J. Heterocycl. Chem. 1977; 14: 807
- 10b Gilis PM, Haemers A, Pattyn SR. Antimicrob. Agents Chemother. 1978; 13: 533
- 10c Bacon ER, Daum SJ. J. Heterocycl. Chem. 1991; 28: 1953
- 10d El-Abadelah MM, Nazer MZ, Okasha SF, Calas M, Bompart J, Mion P. Eur. J. Med. Chem. 1998; 33: 33
- 10e Bompart J, Giral L, Malicorne G, Puygrenier M. Eur. J. Med. Chem. 1987; 22: 139
- 10f Bompart J, Giral L, Malicorne G, Puygrenier M. Eur. J. Med. Chem. 1988; 23: 457
- 10g Sweidan NI, Nazer MZ, El-Abadelah MM, Voelter W. Lett. Org. Chem. 2010; 7: 79
- 10h Al-Jaber HI, El-Abadelah MM, Sabri SS, Al-Tel TH, Voelter W. Z. Naturforsch., B 2009; 64: 1625
- 10i El-Abadelah MM, Sabri SS, Al-Ashqar HA, Mion P, Bompart J, Calas M. Phosphorus, Sulfur Silicon Relat. Elem. 1998; 134–135: 21
- 10j Al-Trawneh SA, El-Abadelah MM, Zahra JA, Al-Taweel SA, Zani F, Incerti M, Cavazzoni A, Vicini P. Bioorg. Med. Chem. 2011; 19: 2541
- 11 Larsen SD, Zhang Z, DiPaolo BA, Manninen PR, Rohrer DC, Hageman MJ, Hopkins TA, Knechtel ML, Oien NL, Rush BD, Schwende FJ, Stefanski KJ, Wieber JL, Wilkinson KF, Zamora KM, Wathen MW, Brideau RJ. Bioorg. Med. Chem. Lett. 2007; 17: 3840
- 12 Zhao G, Iyengar RR, Judd AS, Cool B, Chiou W, Kifle L, Frevert E, Sham H, Kym PR. Bioorg. Med. Chem. Lett. 2007; 17: 3254
- 13a Hardie DG. Endocrinology 2003; 144: 5179
- 13b Hardie DG, Scott JW, Pan DA, Hudson ER. FEBS Lett. 2003; 546: 113
- 13c Kahn BB, Alquier T, Carling D, Hardie DG. Cell Metab. 2005; 1: 15
- 13d Hawley SA, Boudeau J, Reid JL, Mustard KJ, Udd L, Makela TP, Alessi DR, Hardie DG. J. Biol. 2003; 2: 28
-
14 Willemann C, Grünert R, Bednarski PJ, Troschütz R. Bioorg. Med. Chem. 2009; 17: 4406
- 15a Taylor EC, Macor JE. Tetrahedron Lett. 1985; 26: 2419
- 15b Deg’Innocenti A, Funicello M, Scafato P, Spagnolo P, Zanirato P. J. Chem. Soc., Perkin Trans. 1 1996; 561
- 15c Bonini C, Chiummiento L, Funicello M, Spagnolo P. Tetrahedron 2000; 56: 1517
- 16a Berkaoui M, Outurquin F, Paulmier C. Tetrahedron 1998; 54: 9055
- 16b Ragan JA, Raggon JW, Hill PD, Jones BP, McDermott RE, Munchhof MJ, Marx MA, Casavant JM, Cooper BA, Doty JL, Lu Y. Org. Process Res. Dev. 2003; 7: 676
- 16c Nurkkala LJ, Steen RO, Dunne SJ. Synthesis 2006; 1295
- 16d Song Y.-H, Jo BS. J. Heterocycl. Chem. 2009; 46: 1132
- 16e Shestopalov AM, Rodinovskaya LA, Shestopalov AA. J. Comb. Chem. 2010; 12: 9
- 17a Bremner DH, Dunn AD, Wilson KA. Synthesis 1992; 528
- 17b Bremner DH, Dunn AD, Wilson KA, Sturrock KR, Wishart C. Synthesis 1997; 949
- 17c Bremner DH, Dunn AD, Wilson KA, Sturrock KR, Wishart C. Synthesis 1998; 1095
- 17d Comoy C, Banaszak E, Fort Y. Tetrahedron 2006; 62: 6036
- 17e Peixoto D, Begouin A, Queiroz M.-JR. P. Tetrahedron 2012; 68: 7082
- 17f Iaroshenko VO, Ali S, Babar TM, Abbasi MS. A, Sosnovskikh VYa, Villinger A, Tolmachev A, Langer P. Tetrahedron 2013; 69: 3167
- 17g Kobayashi K, Ohmichi T, Miyatani W, Nakagawa K, Yuba S. Heterocycles 2013; 87: 1741
- 18a Kim BS, Kim K. J. Org. Chem. 2000; 65: 3690
- 18b Kiyushi S, Toshiyuki S. EP 1724268, 2006
- 18c Davies RV, Fraser J. US 4710506, 1987
- 18d Boschelli DH, Zhang N, Barrios SA. C, Durutlic H. US 20040242883, 2004
- 18e Davies RV. US 4877793, 1989
- 19 Puvvala S, Jadhav VD, Farooq SM, Patro B, Reddy CV. R. Tetrahedron Lett. 2013; 54: 5043
- 20 Donohoe TJ, Connolly MJ, Walton L. Org. Lett. 2009; 11: 5562
- 21 Karimi B, Hazarkhani H, Zareyee D. Synthesis 2002; 2513
- 22a GVK Biosciences Pvt. Ltd. (Hyderabad) proprietary database.
- 22b The stable 3D structure of each compound was used to calculate its physicochemical properties, such as its molecular weight, number of hydrogen-bond donors (HBD), number of hydrogen-bond acceptors (HBA), AlogP, logD, and polar surface area by using Discovery Studio Version 3.1 (Accelrys, Inc., San Diego, CA).
- 23a Ertl P, Rohde B, Selzer P. J. Med. Chem. 2000; 43: 3714
- 23b Ertl P In Molecular Drug Properties: Measurement and Prediction . Mannhold R. Wiley-VCH; Weinheim: 2007. Chap. 5, 111
- 24 SYBYL 8.0 . Tripos Associates; St. Louis (USA): 2008