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 2020; 52(19): 2892-2898
DOI: 10.1055/s-0040-1707173
DOI: 10.1055/s-0040-1707173
paper
Diastereoselective Synthesis of Pyrazolines by Metal-Free Rearrangement of Bicyclic Triazolines
Further Information
Publication History
Received: 16 April 2020
Accepted after revision: 02 June 2020
Publication Date:
09 July 2020 (online)
Abstract
The metal-free preparation of diazoalkanes through the ring rearrangement of bicyclic triazolines is reported here. Their use in 1,3-dipolar cycloaddition reactions with electron-withdrawing alkenes was investigated. This synthetic procedure allows differently substituted pyrazolines to be obtained in few steps and with high atom economy.
Key words
diazoalkanes - pyrazolines - amidines - 1,3-dipolar cycloaddition - triazoline rearrangement - metal-free reactions - diastereoselectivity - atom economySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707173.
- Supporting Information
-
References
- 1a Zhang Y, Zheng X, Zhang L, Yang Z, Chen L, Wang L, Liu S, Xie Z. Org. Biomol. Chem. 2020; 18: 707
- 1b Locarno S, Eleta-Lopez A, Lupo MG, Gelmi ML, Clerici F, Bittner AM. RSC Adv. 2019; 9: 20565
- 1c Varghese B, Al-Busafi SN, Suliman FO, Al-Kindya SM. Z. RSC Adv. 2017; 7: 46999
- 1d Faria JV, Fazolin VP, Carvalho MA. G, dos Santos MS, Boechat N, Bernardino RA. M. Bioorg. Med. Chem. 2017; 25: 5891
- 1e Korablina DD, Vorozhtsov NI, Sviridova LA, Kalenikova EI, Medvedev OS. Pharm. Chem. J. 2016; 50: 281
- 1f Havrylyuk D, Roman A, Lesyk R. Eur. J. Med. Chem. 2016; 145
- 2a Lellek V, Chen C, Yang W, Ji JL. X. Synlett 2018; 29: 1071
- 2b Alex K, Tillack A, Schwarz N, Beller M, Faesslera R. Org. Lett. 2008; 2377
- 2c Fustero S, Simon-Fuentes A, Sanz-Cervera JF. Org. Prep. Proced. Int. 2009; 41: 253
- 3a Nájera C, Sansano JM, Yus M. Org. Biomol. Chem. 2015; 13: 8596
- 3b Lévai A. J. Heterocycl. Chem. 2002; 39: 1
- 4 Fegheh-Hassanpour Y, Ebrahim F, Arif T, Sintim HO, Claridge TD. W, Amin NT, Hodgson DM. Org. Biomol. Chem. 2018; 16: 2876
- 5 Aronoff MR, Gold B, Raines RT. Org. Lett. 2016; 18: 1538
- 6 Regitz M. Diazo Compounds: Properties and Synthesis. Elsevier; Philadelphia: 2012
- 7 Barluenga J, Quiñones N, Tomás-Gamasa M, Cabal MP. Eur. J. Org. Chem. 2012; 2312
- 8 Liu Z, Li Q, Liao P, Bi X. Chem. Eur. J. 2017; 23: 4756
- 9 Furrow ME, Myers AG. J. Am. Chem. Soc. 2004; 126: 12222
- 10 Allouche EM. D, Charette AB. Chem. Sci. 2019; 10: 3802
- 11 Javed MI, Brewer M. Org. Lett. 2007; 9: 1789
- 12 Contini A, Erba E, Pellegrino S. Synlett 2012; 23: 1523
- 13 Bucci R, Dapiaggi F, Macut H, Pieraccini S, Sironi M, Gelmi ML, Erba E, Pellegrino S. Amino Acids 2020; 52: 15