Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(14): 3227-3238
DOI: 10.1055/a-1799-9339

paper

Synthesis of New Fused 4H-Thieno[3,2-b]pyrrole Derivatives via Decomposition of Methyl 4-Azido-5-arylthiophene-2-carboxylates

Anna L. Samsonenko

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^bFaculty of Chemistry, Silesian University of Technology, Marcina Strzody 9, 44-100 Gliwice, Poland

,

Anastasia S. Kostyuchenko

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^cDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation

,

Tatyana Yu. Zheleznova

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^cDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation

,

Vladislav Yu. Shuvalov

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^cDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation

,

Igor S. Vlasov

^cDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation

,

Alexander S. Fisyuk ∗

^aLaboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation

^cDepartment of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira ave. 55A, Omsk 644077, Russian Federation

› Institutsangaben

Alle Artikel dieser Rubrik

Abstract

This article is focused on the development of practical approaches to the synthesis of 4-azido-5-arylthiophene-2-carboxylates and 4-amino-5-arylthiophene-2-carboxylates using the Fiesselmann reaction. The photochemical and thermal (including microwave-assisted) decomposition of 4-azido-5-arylthiophene-2-carboxylates have been studied in order to synthesize fused 4H-thieno[3,2-b]pyrrole derivatives. The proposed approaches allow to obtain functionally substituted heteroacenes, which are of interest as building blocks for organic semiconductors.

Key words

Key words

conjugation - cyclization - fused-ring system - heterocycles - amines - azides

References
1 Konidena RK, Lee KH, Lee JY, Hong WP. Chem. Asian J. 2019; 14: 2251
2 Konidena RK, Lee KH, Lee JY, Hong WP. Org. Electron. 2019; 70: 211
3 Eom YK, Kang SH, Choi IT, Yoo Y, Kim J, Kim HK. J. Mater. Chem. A 2017; 5: 2297
4 Kil DR, Lu C, Ji J.-M, Kim CH, Kim HK. Nanomaterials 2020; 10: 936
5 Du C, Chen J, Guo Y, Lu K, Ye S, Zheng J, Liu Y, Shuai Z, Yu G. J. Org. Chem. 2009; 74: 7322
6 Zhou F, Liu S, Santarsiero BD, Wink DJ, Boudinet D, Facchetti A, Driver T. Chem. Eur. J. 2017; 23: 12542
7 Ji Q, Gao J, Wang J, Yang C, Hui X, Yan X, Wu X, Xie Y, Wang M.-W. Bioorganic Med. Chem. Lett. 2005; 15: 2891
8 Werner LH, Schroeder DC, Ricca S. J. Am. Chem. Soc. 1957; 79: 1675
9 Buu-Hoï NP, Hien D.-P. Biochem. Pharmacol. 1968; 17: 1227
10 Kolb HC, Walsh JC, Zhang W, Gangadharmath UB, Kasi D, Chen K, Sinha A, Wang E, Chen G, Mocharla VP, Scott PJ. H, Padgett HC, Liang Q, Gao Z, Zhao T, Xia C. Patent WO 2010/011964 A2, 2010
11 Irgashev RA, Steparuk AS, Rusinov GL. Tetrahedron 2020; 76: 131723
12 Huang H, Dang P, Wu L, Liang Y, Liu J. Tetrahedron Lett. 2016; 57: 574
13 Bering L, D’Ottavio L, Sirvinskaite G, Antonchick AP. Chem. Commun. 2018; 54: 13022
14 Zhang P, Li B, Niu L, Wang L, Zhang G, Jia X, Zhang G, Liu S, Ma L, Gao W, Qin D, Chen J. Adv. Synth. Catal. 2020; 362: 2342
15 Zhao X, Li Q, Xu J, Wang D, Zhang-Negrerie D, Du Y. Org. Lett. 2018; 20: 5933
16 Grinev AN, Trofimkin YI, Lomanova EV, Pershin GN, Polukhina LM, Nikolaeva IS, Pushkina TV, Filitis LN, Golovanova EA, Okinshevich OV. Pharm. Chem. J. 1982; 16: 827
17 Appukkuttan P, Van der Eycken E, Dehaen W. Synlett 2005; 127
18 Pudlo M, Csányi D, Moreau F, Hajós G, Riedl Z, Sapi J. Tetrahedron Lett. 2007; 63: 10320
19 Takamatsu K, Hirano K, Satoh T, Miura M. Org. Lett. 2014; 16: 2892
20 Kotwica K, Kostyuchenko AS, Data P, Marszalek T, Skorka L, Jaroch T, Kacka S, Zagorska M, Nowakowski R, Monkman AP, Fisyuk AS, Pisula W, Pron A. Chem. Eur. J. 2016; 22: 11795
21 Kostyuchenko AS, Kurowska A, Zassowski P, Zheleznova TY, Ulyankin EB, Domagala W, Pron A, Fisyuk AS. J. Org. Chem. 2019; 84: 10040
22 Kostyuchenko AS, Wiosna-Salyga G, Kurowska A, Zagorska M, Luszczynska B, Grykien R, Glowacki I, Fisyuk AS, Domagala W, Pron A. J. Mater. Sci. 2016; 51: 2274
23 Chang S.-L, Hung K.-E, Cao F.-Y, Huang K.-H, Hsu C.-S, Liao C.-Y, Lee C.-H, Cheng Y.-J. ACS Appl. Mater. Interfaces 2019; 11: 33179
24 Kostyuchenko AS, Zheleznova TY, Stasyuk AJ, Kurowska A, Domagala W, Pron A, Fisyuk AS. Beilstein J. Org. Chem. 2017; 13: 313
25 Kotwica K, Kurach E, Louarn G, Kostyuchenko AS, Fisyuk AS, Zagorska M, Pron A. Electrochim. Acta 2013; 111: 491
26 Fotsing JR, Hagedorn M, Banert K. Tetrahedron 2005; 61: 8904
27 Shah SR, Navathe SS, Dikundwar AG, Guru Row TN, Vasella AT. Eur. J. Org. Chem. 2013; 264
28 Majo VJ, Perumal PT. J. Org. Chem. 1998; 63: 7136
29 Kostyuchenko AS, Averkov AM, Fisyuk AS. Org. Lett. 2014; 16: 1833
30 Kostyuchenko AS, Drozdova EA, Fisyuk AS. Chem. Heterocycl. Compd. 2017; 53: 92
31 Ulyankin EB, Kostyuchenko AS, Chernenko SA, Bystrushkin MO, Samsonenko AL, Shatsauskas AL, Fisyuk AS. Synthesis 2021; 53: 2422
32 Markley JL, Morse TL, Rath NP, Wencewicz TA. Tetrahedron Lett. 2018; 74: 2743
33 Chen B, Ni H, Guo X, Zhang G, Yu Y. RSC Adv. 2014; 4: 44462
34 Parisien-Collette S, Cruché C, Abel-Snape X, Collins SK. Green Chem. 2017; 19: 4798
35 Caron A, Hernandez-Perez AC, Collins SK. Org. Process Res. Dev. 2014; 18: 1571
36 Bremus-Köbberling E, Gillner A, Avemaria F, Réthoré C, Bräse S. Beilstein J. Org. Chem. 2012; 8: 1213
37 Williams AT. R, Winfield SA, Miller JN. Analyst 1983; 108: 1067
38 Robertson DW, Krushinski JH, Beedle EE, Leander JD, Wong DT, Rathbun RC. J. Med. Chem. 1986; 29: 1577
39 Moumné R, Larue V, Seijo B, Lecourt T, Micouin L, Tisné C. Org. Biomol. Chem. 2010; 8: 1154
40 Takeuchi H, Yanagida S, Ozaki T, Hagiwara S, Eguchi S. J. Org. Chem. 1989; 54: 431
41 Qi T, Qiu W, Liu Y, Zhang H, Gao X, Liu Y, Lu K, Du C, Yu G, Zhu D. J. Org. Chem. 2008; 73: 4638
42 Feng GL, Ji SJ, Lai WY, Huang W. Synlett 2006; 2841

Zusatzmaterial

Supporting Information