Download PDF
Synlett
DOI: 10.1055/a-2579-4076
letter

Divergent Approach to the Synthesis of 2-Aryl-5-(thiophen-2-yl)-1,3,4-oxadiazoles and -1,3,4-thiadiazoles

Anna L. Samsonenko
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
b   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Ave. 55A, Omsk 644077, Russian Federation
,
Anastasia S. Kostyuchenko
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
b   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Ave. 55A, Omsk 644077, Russian Federation
,
Tatyana Y. Zheleznova
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
b   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Ave. 55A, Omsk 644077, Russian Federation
,
Evgenii B. Uliankin
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
b   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Ave. 55A, Omsk 644077, Russian Federation
,
Sergei A. Chernenko
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
b   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Ave. 55A, Omsk 644077, Russian Federation
,
Vladislav Y. Shuvalov 
b   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Ave. 55A, Omsk 644077, Russian Federation
,
Anton L. Shatsauskas 
b   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Ave. 55A, Omsk 644077, Russian Federation
,
Alexander S. Fisyuk  ∗
a   Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave. 11, 644050 Omsk, Russian Federation
b   Department of Organic Chemistry, Omsk F. M. Dostoevsky State University, Mira Ave. 55A, Omsk 644077, Russian Federation
› Author Affiliations
This work was supported by the Russian Science Foundation (Grant No. 20-73-10043).
› Further Information
   Permissions and Reprints All articles of this category


Abstract

The reaction of 2-(chloromethyl)-1,3,4-thiadiazoles and -1,3,4-oxadiazoles with thioacetic acid in the presence of DIPEA led to the formation of S-[(1,3,4-thiadiazol-2-yl)methyl]- and [(1,3,4-oxadiazol-2-yl)methyl]ethanethioate. A series of 2-thienyl-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles were obtained by the reaction of 3-chloroacrylaldehydes with (1,3,4-thiadiazol-2-yl)- and (1,3,4-oxadiazol-2-yl)methanethiols formed in situ from S-[(1,3,4-thia(oxa)diazol-2-yl)methyl]ethanethioate in methanol in the presence of K2CO3. The photophysical properties of the synthesized compounds were studied.

Key words

3-chloroacrylaldehydes - 1,3,4-oxadiazoles - 1,3,4-thiadiazoles - divergent synthesis - heterocycles

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2579-4076.
  • Supporting Information


Publication History

Received: 01 March 2025

Accepted after revision: 09 April 2025

Accepted Manuscript online:
09 April 2025

Article published online:
28 May 2025

© 2025. Thieme. All rights reserved

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany

 

  • References

  • 1 Li Z, Zhan P, Liu X. Mini-Rev. Med. Chem. 2011; 11: 1130
    PubMedSearch in Google Scholar
  • 2 Bajaj S, Asati V, Singh J, Roy PP. Eur. J. Med. Chem. 2015; 97: 124
    CrossrefPubMedSearch in Google Scholar
  • 3 Salahuddin, Mazumder A, Yar MS, Mazumder R, Chakraborthy GS, Ahsan MJ, Rahman MU. Synth. Commun. 2017; 47: 1805
    CrossrefSearch in Google Scholar
  • 4 Chaudhary T, Upadhyay PK. Curr. Org. Synth. 2022; 19: 731
    PubMedSearch in Google Scholar
  • 5 Luczynski M, Kudelko A. Appl. Sci. 2022; 12: 3756
    Search in Google Scholar
  • 6 Verma SK, Verma R, Kumar KS. S, Banjare L, Shaik AB, Bhandare RR, Rakesh KP, Rangappa KS. Eur. J. Med. Chem. 2021; 219: 113442
    PubMedSearch in Google Scholar
  • 7 Hu Y, Li C.-Y, Wang X.-M, Yang Y.-H, Zhu H.-L. Chem. Rev. 2014; 114: 5572
    CrossrefPubMedSearch in Google Scholar
  • 8 Santhosh CR, Chinnam S, Kottam N, Amreen S, Ananthnag GS, Madhu GM, Gadde S, Fernandes VT, Arnipalli H. Results Chem. 2025; 13: 101939
    Search in Google Scholar
  • 9 De Oliveira CS, Lira BF, Barbosa-Filho JM, Lorenzo JG. F, De Athayde-Filho PF. Molecules 2012; 17: 10192
    CrossrefPubMedSearch in Google Scholar
  • 10 El-Masry RM, Kadry HH, Taher AT, Abou-Seri SM. Molecules 2022; 27: 2709
    PubMedSearch in Google Scholar
  • 11 Savarino A. Expert Opin. Invest. Drugs 2006; 15: 1507
    Search in Google Scholar
  • 12 James ND, Growcott JW. Drugs Future 2009; 34: 624
    Search in Google Scholar
  • 13 Stoikov II, Antipina IS, Burilov VA, Kurbangalieva AR, Rostovskii NV, Pankova AS, Balova IA, Remizov YO, Pevzner LM, Petrov ML, Vasilyev AV, Averin AD, Beletskaya IP, Nenajdenko VG, Beloglazkina EK, Gromov SP, Karlov SS, Magdesieva TV, Prishchenko AA, Popkov SV, Terent’ev AO, Tsaplin GV, Kustova TP, Kochetova LB, Magdalinova NA, Krasnokutskaya EA, Nyuchev AV, Kuznetsova YL, Fedorov AY, Egorova AY, Grinev VS, Sorokin VV, Ovchinnikov KL, Kofanov ER, Kolobov AV, Rusinov VL, Zyryanov GV, Nosova EV, Bakulev VA, Belskaya NP, Berezkina TV, Obydennov DL, Sosnovskikh VY, Bakhtin SG, Baranova OV, Doroshkevich VS, Raskildina GZ, Sultanova RM, Zlotskii SS, Dyachenko VD, Dyachenko IV, Fisyuk AS, Konshin VV, Dotsenko VV, Ivleva EA, Reznikov AN, Klimochkin YN, Aksenov DA, Aksenov NA, Aksenov AV, Burmistrov VV, Butov GM, Novakov IA, Shikhaliev KhS, Stolpovskaya NV, Medvedev SM, Kandalintseva NV, Prosenko OI, Menshchikova EB, Golovanov AA, Khashirovа SY. Russ. J. Org. Chem. 2024; 60: 1361
    CrossrefSearch in Google Scholar
  • 14 Charushin VN, Verbitskiy EV, Chupakhin ON, Vorobyeva DV, Gribanov PS, Osipov SN, Ivanov AV, Martynovskaya SV, Sagitova EF, Dyachenko VD, Dyachenko IV, Krivokolylsko SG, Dotsenko VV, Aksenov AV, Aksenov DA, Aksenov NA, Larin AA, Fershtat LL, Muzalevskiy VM, Nenajdenko VG, Gulevskaya AV, Pozharskii AF, Filatova EA, Belyaeva KV, Trofimov BA, Balova IA, Danilkina NA, Govdi AI, Tikhomirov AS, Shchekotikhin AE, Novikov MS, Rostovskii NV, Khlebnikov AF, Klimochkin YN, Leonova MV, Tkachenko IM, Mamedov VA. O, Mamedova VL, Zhukova NA, Semenov VE, Sinyashin OG, Borshchev OV, Luponosov YN, Ponomarenko SA, Fisyuk AS, Kostyuchenko AS, Ilkin VG, Beryozkina TV, Bakulev VA, Gazizov AS, Zagidullin AA, Karasik AA, Kukushkin ME, Beloglazkina EK, Golantsov NE, Festa AA, Voskresenskii LG, Moshkin VS, Buev EM, Sosnovskikh VY, Mironova IA, Postnikov PS, Zhdankin VV, Yusubov MS. O, Yaremenko IA, Vil’ VA, Krylov IB, Terent’ev AO, Gorbunova YG, Martynov AG, Tsivadze AY, Stuzhin PA, Ivanova SS, Koifman OI, Burov ON, Kletskii ME, Kurbatov SV, Yarovaya OI, Volcho KP, Salakhutdinov NF, Panova MA, Burgart YV, Saloutin VI, Sitdikova AR, Shchegravina ES, Fedorov AY. Russ. Chem. Rev. 2024; 93: RCR5125
    CrossrefSearch in Google Scholar
  • 15 Kostyuchenko AS, Kurowska A, Zassowski P, Zheleznova TY, Ulyankin EB, Domagala W, Pron A, Fisyuk AS. J. Org. Chem. 2019; 84: 10040
    CrossrefPubMedSearch in Google Scholar
  • 16 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
    CrossrefPubMedSearch in Google Scholar
  • 17 Deshapande N, Belavagi NS, Sunagar MG, Gaonkar S, Pujar GH, Wari MN, Inamdar SR, Khazi IA. M. RSC Adv. 2015; 5: 86685
    Search in Google Scholar
  • 18 Belavagi NS, Deshapande N, Pujar GH, Wari MN, Inamdar SR, Khazi IA. M. J. Fluoresc. 2015; 25: 1323
    CrossrefPubMedSearch in Google Scholar
  • 19 Xu H, Lartey PO, Wu Y, Liang X, Zhang F, Li D, Li B, Zhang Z, Wang S, Guo K, Ma J. Dyes Pigments 2021; 193: 109483
    Search in Google Scholar
  • 20 Najare MS, Patil MK, Nadaf AA, Mantur S, Garbhagudi M, Gaonkar S, Inamdar SR, Khazi IA. M. J. Mol. Struct. 2020; 1199: 127032
    Search in Google Scholar
  • 21 Tang L, Zheng Z, Zhong K, Bian Y. Tetrahedron Lett. 2016; 57: 1361
    Search in Google Scholar
  • 22 Diana R, Caruso U, Di Costanzo L, Concilio S, Piotto S, Sessa L, Panunzi B. Molecules 2022; 27: 1824
    PubMedSearch in Google Scholar
  • 23 Kotwica K, Kurach E, Louarn G, Kostyuchenko AS, Fisyuk AS, Zagorska M, Pron A. Electrochim. Acta 2013; 111: 491
    CrossrefSearch in Google Scholar
  • 24 Samsonenko AL, Kostyuchenko AS, Zheleznova TY, Shuvalov VY, Uliankin EB, Shatsauskas AL, Fisyuk AS. Synthesis 2024; 56: 2423
    Thieme ConnectSearch in Google Scholar
  • 25 Ulyankin EB, Kostyuchenko AS, Chernenko SA, Bystrushkin MO, Samsonenko AL, Shatsauskas AL, Fisyuk AS. Synthesis 2021; 53: 2422
    Thieme ConnectSearch in Google Scholar
  • 26 Kanomata N, Nakata T. Heterocycles 1998; 48: 2551
    Search in Google Scholar
  • 27 Kostyuchenko AS, Averkov AM, Fisyuk AS. Org. Lett. 2014; 16: 1833
    CrossrefPubMedSearch in Google Scholar
  • 28 Avval MM, Murthy VS, Shashikanth S. Res. J. Pharm. Biol. Chem. Sci. 2014; 5: 441
    Search in Google Scholar
  • 29 Meshram GA, Vala VA. Chem. Heterocycl. Compd. 2015; 51: 44
    Search in Google Scholar
  • 30 He F, Wei P, Yu G, Guo S, Zheng Z, Chen S, Dai A, Zhang R, Wu Z, Wu J. Bioorg. Chem. 2021; 115: 105248
    PubMedSearch in Google Scholar
  • 31 Abulwerdi FA, Shortridge MD, Sztuba-Solinska J, Wilson R, Le Grice SF. J, Varani G, Schneekloth JS. J. Med. Chem. 2016; 59: 11148
    PubMedSearch in Google Scholar
  • 32 Zhang K, Wang P, Xuan L.-N, Fu X.-Y, Jing F, Li S, Liu Y.-M, Chen B.-Q. Bioorg. Med. Chem. Lett. 2014; 24: 5154
    PubMedSearch in Google Scholar
  • 33 Cao S, Wei N, Zhao C, Li L, Huang Q, Qian X. J. Agric. Food Chem. 2005; 53: 3120
    PubMedSearch in Google Scholar
  • 34 Yang F, Lu W, Zhang H, Fan S, Qiu H. CN117024375, 2023
  • 36 Kostyuchenko AS, Zheleznova TY, Stasyuk AJ, Kurowska A, Domagala W, Pron A, Fisyuk AS. Beilstein J. Org. Chem. 2017; 13: 313
    CrossrefPubMedSearch in Google Scholar