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
Download PDF
Synthesis 2024; 56(09): 1465-1475
DOI: 10.1055/s-0042-1751555
DOI: 10.1055/s-0042-1751555
paper
Tertiary Amines as Temporary Masked Secondary Amines: A Direct Access to 5-Dialkylamino-1,2,4-oxadiazoles from 1,2,4-Oxadiazol-5(4H)-ones
Authors
Financial support for this work was partially provided by Chiang Mai University (Grant No. MRCMU2566R_016 to W.P.).
Abstract
A novel strategy utilizing tertiary amines as temporary masked secondary amines to synthesize 5-dialkylamino 1,2,4-oxadiazoles via Ph3P-I2 mediated amination of 1,2,4-oxadiazol-5(4H)-ones was developed. A one-step N-dealkylative functionalization of tertiary amines with the 1,2,4-oxadiazole ring enables a convenient access to diverse 5-amino-1,2,4-oxadiazoles. Additionally, orthogonally functionalized piperazine derivatives can be effectively constructed through site-selective reaction of 1,4-dialkylpiperazines or via a sequential N-functionalization of 1-methylpiperazine obviating laborious protection/deprotection steps.
Key words
1,2,4-oxadiazolones - 1,2,4-oxadiazoles - triphenylphosphine - iodine - amination - tertiary aminesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751555.
- Supporting Information (PDF)
Publication History
Received: 06 December 2023
Accepted after revision: 17 January 2024
Article published online:
12 February 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Atmaram UA, Roopan SM. Appl. Microbiol. Biotechnol. 2022; 106: 3489
- 1b Biernacki K, Dasko M, Ciupak O, Kubinski K, Rachon J, Demkowicz S. Pharmaceuticals 2020; 13: 111
- 1c Desai N, Monapara J, Jethawa A, Khedkar V, Shingate B. Arch. Pharm. (Weinheim) 2022; 355: 2200123
- 1d Hendawy OM. Arch. Pharm. (Weinheim) 2022; 355: 2200045
- 2 Camci M, Karali N. ChemMedChem 2023; 18: e202200638
- 3a Ispikoudi M, Amvrazis M, Kontogiorgis C, Koumbis AE, Litinas KE, Hadjipavlou-Litina D, Fylaktakidou KC. Eur. J. Med. Chem. 2010; 45: 5635
- 3b Showell GA, Gibbons TL, Kneen CO, MacLeod AM, Merchant K, Saunders J, Freedman SB, Patel S, Baker R. J. Med. Chem. 1991; 34: 1086
- 3c Street LJ, Baker R, Book T, Kneen CO, MacLeod AM, Merchant KJ, Showell GA, Saunders J, Herbert RH. J. Med. Chem. 1990; 33: 2690
- 4 Xue D, Xu Y, Kyani A, Roy J, Dai L, Sun D, Neamati N. J. Med. Chem. 2022; 65: 343
- 5a Li G, Meng B, Yuan B, Huan Y, Zhou T, Jiang Q, Lei L, Sheng L, Wang W, Gong N, Lu Y, Ma C, Li Y, Shen Z, Huang H. Eur. J. Med. Chem. 2020; 188: 112017
- 5b Kim H, Kim M, Oh K, Lee S, Lim S, Lee S, Kim YH, Suh KH, Min KH. Eur. J. Med. Chem. 2023; 258: 115584
- 6 Horan JC, Sanyal S, Choi Y, Hill-Drzewi M, Patnaude L, Anderson S, Fogal S, Mao C, Cook BN, Gueneva-Boucheva K, Fisher MB, Hickey E, Pack E, Bannen LC, Chan DS, Mac MB, Ng SM, Wang Y, Xu W, Modis LK, Lemieux RM. Bioorg. Med. Chem. Lett. 2014; 24: 4807
- 7 Bartolozzi A, Abeywardane A, Bosanac T, Broadwater JA, Chen Z, Hutzler JM, Huber JD, Nemoto P, Olague A, Riether D, Simpson T, Takahashi H, Wu L, Zhang Y, Zindell RM. Bioorg. Med. Chem. Lett. 2017; 27: 4652
- 8a Muraglia E, Ontoria JM, Branca D, Dessole G, Bresciani A, Fonsi M, Giuliano C, Llauger Bufi L, Monteagudo E, Palumbi MC, Torrisi C, Rowley M, Steinkuehler C, Jones P. Bioorg. Med. Chem. Lett. 2011; 21: 5283
- 8b Ontoria JM, Bufi LL, Torrisi C, Bresciani A, Giomini C, Rowley M, Serafini S, Bin H, Hao W, Steinkuehler C, Jones P. Bioorg. Med. Chem. Lett. 2011; 21: 5274
- 9a Baykov SV, Shetnev AA, Semenov AV, Baykova SO, Boyarskiy VP. Int. J. Mol. Sci. 2023; 24: 5406
- 9b Pace A, Pierro P. Org. Biomol. Chem. 2009; 7: 4337
- 10 Bolton RE, Coote SJ, Finch H, Lowdon A, Pegg N, Vinader MV. Tetrahedron Lett. 1995; 36: 4471
- 11a Kono M, Matsumoto T, Kawamura T, Nishimura A, Kiyota Y, Oki H, Miyazaki J, Igaki S, Behnke CA, Shimojo M, Kori M. Bioorg. Med. Chem. 2013; 21: 28
- 11b Matsuoka RT, Boros EE, Brown AD, Bullock KM, Canoy WL, Carpenter AJ, Cobb JD, Condon SE, Deschamps NM, Elitzin VI, Erickson G, Fang JM, Igo DH, Joshi BK, Kaldor IW, Mitchell MB, Peckham GE, Reynolds DW, Salmon MC, Sharp MJ, Tabet EA, Toczko JF, Wu LM, Zhou X.-mM. Org. Process Res. Dev. 2016; 20: 1469
- 11c Jakopin Z. Tetrahedron Lett. 2018; 59: 4320
- 12 Goldberg K, Clarke DS, Scott JS. Tetrahedron Lett. 2014; 55: 4433
- 13a Su D, Duan H, Wei Z, Cao J, Liang D, Lin Y. Tetrahedron Lett. 2013; 54: 6959
- 13b Bolotin DS, Kulish KI, Bokach NA, Starova GL, Gurzhiy VV, Kukushkin VY. Inorg. Chem. 2014; 53: 10312
- 13c Lukin A, Kalinchenkova N, Vedekhina T, Zhurilo N, Krasavin M. Tetrahedron Lett. 2018; 59: 2732
- 14 Levins CG, Wan Z.-K. Org. Lett. 2008; 10: 1755
- 15a Zhang R.-H, Guo H.-Y, Deng H, Li J, Quan Z.-S. J. Enzyme Inhib. Med. Chem. 2021; 36: 1165
- 15b Brito AF, Moreira LK. S, Menegatti R, Costa EA. Fundam. Clin. Pharmacol. 2019; 33: 13
- 15c Shaquiquzzaman M, Verma G, Marella A, Akhter M, Akhtar W, Khan MF, Tasneem S, Alam MM. Eur. J. Med. Chem. 2015; 102: 487
- 15d Singh K, Siddiqui HH, Shakya P, Bagga P, Kumar A, Khalid M, Arif M, Alok S. Int. J. Pharm. Sci. Res. 2015; 6: 4145
- 16 Taylor RD, MacCoss M, Lawson AD. G. J. Med. Chem. 2014; 57: 5845
- 17 Pattarawarapan M, Yamano D, Wiriya N, Phakhodee W. J. Org. Chem. 2019; 84: 6516
- 18 Pattarawarapan M, Yamano D, Wiriya N, Hongsibsong S, Phakhodee W. Eur. J. Org. Chem. 2022; e202201069
- 19a Lee M, Rucil T, Hesek D, Oliver AG, Fisher JF, Mobashery S. J. Org. Chem. 2015; 80: 7757
- 19b Hamilton GL, Backes BJ. Tetrahedron Lett. 2006; 47: 2229
- 19c Bao Y.-S, Bao Z, Bao A, Baiyin M, Jia M. J. Org. Chem. 2014; 79: 803
- 20a Tornieporth-Oetting I, Klapoetke T. J. Organomet. Chem. 1989; 379: 251
- 20b Morcillo SP, Alvarez de Cienfuegos L, Mota AJ, Justicia J, Robles R. J. Org. Chem. 2011; 76: 2277
- 21a Kumar A, Akula HK, Lakshman MK. Eur. J. Org. Chem. 2010; 2709
- 21b Duangkamol C, Wangngae S, Pattarawarapan M, Phakhodee W. Eur. J. Org. Chem. 2014; 7109
- 22a Paul S, Panda S, Manna D. Tetrahedron Lett. 2014; 55: 2480
- 22b Cristau H.-J, Hammami A, Manginot E, Torreilles E. Phosphorus, Sulfur Silicon Relat. Elem. 1998; 134/135: 475
- 23 Karanam P, Reddy GM, Koppolu SR, Lin W. Tetrahedron Lett. 2018; 59: 59
- 24a Wang Q, Su Y, Li L, Huang H. Chem. Soc. Rev. 2016; 45: 1257
- 24b Liu S, Zhao Z, Wang Y. Chem. Eur. J. 2019; 25: 2423
- 24c Liu C, Chen H.-N, Xiao T.-F, Hu X.-Q, Xu P.-F, Xu G.-Q. Chem. Commun. 2023; 59: 2003
- 24d Yang D, Shi J, Chen J, Jia X, Shi C, Ma L, Li Z. RSC Adv. 2021; 11: 18966
- 24e Zhang Z, Liu F, Chen J, Zhou K, Bao Z, Su B, Yang Q, Ren Q, Yang Y. Tetrahedron Lett. 2019; 60: 151191
- 25a Najmi AA, Bischoff R, Permentier HP. Molecules 2022; 27: 3293
- 25b Thavaneswaran S, McCamley K, Scammells PJ. Nat. Prod. Commun. 2006; 1: 885
- 25c von Braun J. Ber. Dtsch. Chem. Ges. 1900; 33: 1438
- 25d Cooley JH, Evain EJ. Synthesis 1989; 1
- 25e Miller MW, Vice SF, McCombie SW. Tetrahedron Lett. 1998; 39: 3429
- 25f Paritosh RD, Kumar KA, Duddu R, Axenrod T, Dai R, Das KK, Guan X.-P, Sun J, Trivedi NJ. J. Org. Chem. 2000; 65: 1207
- 25g Polonovski M, Polonovski M. Bull. Soc. Chim. Fr. 1927; 1190
- 25h Thavaneswaran S, Scammells PJ. Bioorg. Med. Chem. Lett. 2006; 16: 2868
- 26 Yu X, Chen K, Yang F, Zha S, Zhu J. Org. Lett. 2016; 18: 5412
- 27 Chennakrishnareddy G, Debasis H, Jayan R, Manjunatha SG. Tetrahedron Lett. 2011; 52: 6170
- 28 Eloy F, Lenaers R. Helv. Chim. Acta 1966; 49: 1430