Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2022; 54(16): 3658-3666
DOI: 10.1055/s-0041-1738070
DOI: 10.1055/s-0041-1738070
paper
One-Pot Syntheses of Substituted 2-Aminothiazoles and 2-Aminoselenazoles via Meerwein Arylation of Alkyl Vinyl Ketones
The authors thank the National Research Foundation of Ukraine (Project 2020.01/0166 ‘New azole and cage-like agents against cancer and pathogenic microorganisms’).
Abstract
Both one-pot and two-step procedures for the synthesis of substituted 2-aminothiazoles and 2-aminoselenazoles are described. Anilines are first converted into arenediazonium bromides, which are then reacted with methyl vinyl ketone or cyclopropyl vinyl ketone in the presence of copper(II) bromide to give 4-aryl-3-bromobutan-2-ones (40–71%) and 3-aryl-2-bromo-1-cyclopropylpropan-1-ones (41–79%), respectively. These products are reacted, without prior isolation, with thiourea or selenourea to prepare 4-methyl- and 4-cyclopropyl-5-(R-benzyl)thiazol-2-amines (14 examples) and their selenium analogs (14 examples). The yields of the one-pot procedure are higher (40–81%) than those of the two-step procedure (32–70%).
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1738070.
- Supporting Information
Publication History
Received: 02 March 2022
Accepted after revision: 28 March 2022
Article published online:
03 May 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Alizadeh SR, Hashemi SM. Med. Chem. Res. 2021; 30: 771
- 1b Petrou A, Fesatidou M, Geronikaki A. Molecules 2021; 26: 3166
- 1c Chowdhury A, Patel S, Sharma A, Das A, Meshram P, Shard A. Chem. Heterocycl. Compd. 2020; 56: 455
- 1d Das D, Sikdar P, Bairagi M. Eur. J. Med. Chem. 2016; 109: 89
- 2a Wan Y, Long J, Gao H, Tang Z. Eur. J. Med. Chem. 2021; 210: 112953
- 2b Bestgen B, Krimm I, Kufareva I, Kamal AA. M, Seetoh W.-G, Abell C, Hartmann RW, Abagyan R, Cochet C, Le Borgne M, Engel M, Lomberget T. J. Med. Chem. 2019; 62: 1803
- 3 Suresh G, Nadh RV, Srinivasu N, Yennity D. Lett. Org. Chem. 2018; 15: 1070
- 4 Ouyang B, Wang L, Qi J, Fan M, Wang H, Yao L. Biol. Pharm. Bull. 2020; 43: 1154
- 5 Özbek O, Gürdere MB. Phosphorus, Sulfur Silicon Relat. Elem. 2021; 196: 444
- 6 Finiuk N, Klyuchivska O, Ivasechko I, Hreniukh V, Ostapiuk Y, Shalai Y, Panchuk R, Matiychuk V, Obushak M, Stoika R, Babsky A. Anti-Cancer Drugs 2019; 30: 27
- 7a Stefanska J, Nowicka G, Struga M, Szulczyk D, Koziol AE, Augustynowicz-Kopec E, Napiorkowska A, Bielenica A, Filipowski W, Filipowska A, Drzewiecka A, Giliberti G, Madeddu S, Boi S, La Colla P, Sanna G. Chem. Pharm. Bull. 2015; 63: 225
- 7b Elshaarawy RF. M, Mustafa FH. A, Sofy AR, Hmed AA, Janiak C. J. Environ. Chem. Eng. 2019; 7: 102800
- 8 Kesicki EA, Bailey MA, Ovechkina Y, Early JV, Alling T, Bowman J, Zuniga ES, Dalai S, Kumar N, Masquelin T, Hipskind PA, Odingo JO, Parish T. PLoS ONE 2016; 11: e0155209
- 9 Bitencourt Brito CC, Carneiro da Silva HV, Brondani DJ, de Faria AR, Ximenes RM, da Silva IM, de Albuquerque JF. C, Santos Castilho M. J. Enzyme Inhib. Med. Chem. 2019; 34: 333
- 10a Yakupova LR, Nasibullina RA, Shamukaev VA, Sultanova RM, Safiullin RL. Kinet. Catal. 2020; 61: 232
- 10b Sofan MA, El-Mekabaty A, Hasel AM, Said SB. J. Heterocycl. Chem. 2021; 58: 1645
- 10c Al-Anazi KM, Mahmoud AH, AbulFarah M, Allam AA, Fouda MM. G, Gaffer HE. ChemistrySelect 2019; 4: 5570
- 11 Hussein AH. M, Khames AA, El-Adasy A.-BA, Atalla AA, Abdel-Rady M, Hassan MI. A, Abou-Salim MA, Elshaier YA. M. M, Barakat A. Molecules 2021; 26: 902
- 12a Ravi BN, Keshavayya J, Mallikarjuna NM, Kumar V, Kandgal S. J. Mol. Struct. 2020; 1204: 127493
- 12b Fedyshyn O, Bazel Y, Fizer M, Sidey V, Imrich J, Vilkova M, Barabash O, Ostapiuk Y, Tymoshuk O. J. Mol. Liq. 2020; 304: 112713
- 12c Elmaaty TA, Ramadan SM, El-Nagar K, Zaghloul D, El-Taweel F. Fibers Polym. 2020; 21: 2292
- 12d Penthala R, Heo G, Kim H, Lee IY, Ko EH, Son Y.-A. J. CO2 Util. 2020; 38: 49
- 12e Rajeshirke M, Kadam M, Sekar N. Fibers Polym. 2019; 20: 320
- 12f Pithan PM, Kuhlmann C, Engelhard C, Ihmels H. Chem Eur. J. 2019; 25: 16088
- 13a Farahati R, Ghaffarinejad A, Mousavi-Khoshdel SM, Rezania J, Behzdai H, Shockravi A. Prog. Org. Coat. 2019; 132: 417
- 13b Yang X, Zhang W. RSC Adv. 2019; 9: 10454
- 13c Guo L, Kaya S, Obot IB, Zheng X, Qiang Y. J. Colloid Interface Sci. 2017; 506: 478
- 14a Radhakrishnan R, Sreejalekshmi KG. J. Org. Chem. 2018; 83: 3453
- 14b Potopnyk MA, Lytvyn R, Danyliv Y, Ceborska M, Bezvikonnyi O, Volyniuk D, Gražulevičius JV. J. Org. Chem. 2018; 83: 1095
- 15 Furet P, Guagnano V, Fairhurst RA, Imbach-Weese P, Bruce I, Knapp M, Fritsch C, Blasco F, Blanz J, Aichholz R, Hamon J, Fabbro D, Caravatti G. Bioorg. Med. Chem. Lett. 2013; 23: 3741
- 16a Shareef MA, Devi GP, Routhu SR, Kuar CG, Kamal A, Babu BN. RSC Med. Chem. 2020; 11: 1178
- 16b Claudio-Catalán MA, Pharande SG, Quezada-Soto A, Kishore KG, Rentería-Gómez A, Padilla-Vaca F, Gámez-Montaño R. ACS Omega 2018; 3: 5177
- 17 Vahter J, Viht K, Uri A, Manoharan GB, Enkvist E. Bioorg. Med. Chem. 2018; 26: 5062
- 18 Araškova JB, Nikolića M, Armaković S, Armaković S, Rodić M, Višnjevac A, Padrón JM, Todorović TR, Filipović NR. J. Mol. Struct. 2021; 1240: 130512
- 19a Dzedulionytė K, Voznikaitė P, Bieliauskas A, Malinauskienė V, Sløk FA, Šačkus A. Molbank 2021; 2021: M1207
- 19b Radatz CS, Coelho FL, Gil ES, da Silveira Santos F, Forain Miolo Schneider JM, Gonçalves PF. B, Rodembusch FS, Schneider PH. J. Mol. Struct. 2020; 1207: 127817
- 20a Nishina A, Sekiguchi A, Fukumoto R.-h, Koketsu M, Furukawa S. Biochem. Biophys. Res. Commun. 2007; 352: 360
- 20b Wang H, Yue Y, Zhao H, Wu H, Jiang K, Li S, Zhao M, Lin F. Neurotoxic. Res. 2021; 39: 841
- 21a Poerschke RL, Moos PJ. Biochem. Pharmacol. 2011; 81: 211
- 21b Angeli A, Trallori E, Ferraroni M, Di Cesare Mannelli L, Ghelardini C, Supuran CT. Eur. J. Med. Chem. 2018; 157: 1214
- 22 Laczkowski K, Misiura K, Biernasiuk A, Malm A. Med. Chem. 2015; 11: 118
- 23 Laczkowski KZ, Biernasiuk A, Baranowska-Laczkowsky Zielinska S, Salat K, Furgala A, Misiura K, Malm A. J. Enzyme Inhib. Med. Chem. 2016; 31: 24
- 24 Kuchar J, Reinhold K, Rösgen V, Nöthling N, Lehmann CW, Mohr F. Molecules 2021; 26: 7695
- 25 Malinauskienė V, Kveselytė A, Dzedulionytė K, Bieliauskas A, Burinskas S, Sløk FA, Šačkus A. Chem. Heterocycl. Compd. 2018; 54: 469
- 26a Wang Z.-L, Chen J, He Y.-H, Guan Z. J. Org. Chem. 2021; 86: 3741
- 26b Husain AA, Bisht KS. J. Org. Chem. 2020; 85: 9928
- 27 Liu H.-W, Fang Y, Wang S.-Y, Ji S.-J. J. Org. Chem. 2020; 85: 3508
- 28 Fu R.-G, Wang Y, Xia F, Zhang H.-L, Sun Y, Yang D.-W, Wang Y.-W, Yin P. J. Org. Chem. 2019; 84: 12237
- 29a Erian AW, Sherif SM, Gaber HM. Molecules 2003; 8: 793
- 29b Pravst I, Zupan M, Stavber S. Tetrahedron 2008; 64: 5191
- 30a Meerwein H, Buchner E, van Emster K. J. Prakt. Chem. 1939; 152: 237
- 30b Kindt S, Heinrich MR. Synthesis 2016; 48: 1597
- 30c Mo F, Qiu D, Zhang L, Wang J. Chem. Rev. 2021; 121: 5741
- 30d Shukla CA, Atapalkar RS, Kulkarni AA. Org. Process Res. Dev. 2020; 24: 1658
- 30e Batsyts S, Shehedyn M, Goreshnik EA, Obushak MD, Schmidt A, Ostapiuk YV. Eur. J. Org. Chem. 2019; 7842
- 30f Ostapiuk YV, Shehedyn M, Barabash OV, Demydchuk B, Batsyts S, Herzberger C, Schmidt A. Synthesis 2022; 54: 732
- 31 Ostapiuk YV, Matiichuk VS, Pidlypnyi NI, Obushak ND. Russ. J. Org. Chem. 2012; 48: 519
- 32 Obushak ND, Matiichuk VS, Vasylyshin RYa, Ostapyuk YuV. Russ. J. Org. Chem. 2004; 40: 383
- 33a Nagarajaiah H, Prasad NL, Begum NS. Polycycl. Aromat. Compd. 2022; DOI: DOI: 10.1080/10406638.2020.1821228.
- 33b de Andrade VS. C, de Mattos MC. S. Tetrahedron Lett. 2020; 61: 152164
- 33c Zarnegar Z, Sadeghi M, Alizadeh R, Safai J. J. Mol. Liq. 2018; 255: 76
- 33d Zhu Y, Chen W, Zhao D, Zhang G, Yu Y. Synthesis 2019; 51: 2023
- 33e Németh AGy, Marlok B, Domján A, Gao Q, Han X, Keserü GM, Ábrányi-Balogh P. Eur. J. Org. Chem. 2021; 3587
- 34a Matiichuk Y, Ostapiuk Y, Chaban T, Sulyma M, Sukhodolska N, Matiychuk V. Biointerface Res. Appl. Chem. 2020; 10: 6597
- 34b Mummel S, Lederle F, Hübner E, Namyslo JC, Nieger M, Schmidt A. Angew. Chem. Int. Ed. 2021; 60: 18882 ; Angew. Chem. 2021, 133, 19032
- 34c Liu M, Nieger M, Hübner EG, Schmidt A. Chem. Eur. J. 2016; 22: 5416
- 34d Schmidt A, Snovydovych B, Gjikaj M. Synthesis 2008; 2798
- 34e Schmidt A, Beutler A, Habeck T, Mordhorst T, Snovydovych B. Synthesis 2006; 1882
- 34f Schmidt A, Nieger M. Heterocycles 1999; 51: 2119
- 35a Ostapiuk Y, Frolov D, Vasylyschyn R, Matiychuk V. Biopolymers Cell 2018; 34: 59
- 35b Ostapiuk YV, Chaban TI, Matiychuk VS. Russ. J. Org. Chem. 2020; 56: 1495
- 35c Storm AT, Nieger M, Gjikaj M, Namyslo JC, Adams J, Schmidt A. Eur. J. Org. Chem. 2021; 34: 4803
- 36 Rahimi A, Namyslo JC, Drafz MH. H, Halm J, Hübner EG, Nieger M, Rautzenberg N, Schmidt A. J. Org. Chem. 2011; 76: 7316
- 37a Hillrichs K, Namyslo JC, Lederle F, Hübner EG, Schmidt A. Synthesis 2022; 54 DOI: 10.1055/s-0040-1719912.
- 37b Deev S, Batsyts S, Sheina E, Shestakova TS, Khalimbadzha I, Kiskin MA, Charushin V, Chupakhin O, Paramonov AS, Shenkarev ZO, Namyslo JC, Schmidt A. Eur. J. Org. Chem. 2020; 450
- 37c Batsyts S, Vedmid R, Namyslo JC, Nieger M, Schmidt A. Eur. J. Org. Chem. 2019; 1301
- 37d Zhang J, Hübner EG, Namyslo JC, Nieger M, Schmidt A. Org. Biomol. Chem. 2018; 16: 6801
- 37e Liu M, Nieger M, Schmidt A. Chem. Commun. 2015; 51: 477
- 38 Bates FX, Donnelly JA, Keegan JR. Tetrahedron 1991; 47: 4991
Selected examples:
Selected examples: