One-Pot Synthesis of 1,2,3-Triazole-Fused Polycyclic Systems via Sequential Annulation of 1,n-Enynes with Tosyl Azide

Abstract

An efficient one-pot sequential annulation of 1,n-enynes with tosyl azide is reported, providing a series of novel N-alkyl 1,2,3-triazole-fused polycyclic scaffolds in moderate to excellent yields under mild reaction conditions.

Key words

1,n-enyne - tosyl azide - fused 1,2,3-triazole - one-pot reaction - cyclization

Publikationsverlauf

Eingereicht: 13. Juni 2022

Angenommen nach Revision: 05. Juli 2022

Accepted Manuscript online:
05. Juli 2022

Artikel online veröffentlicht:
09. August 2022

• References


For selected books, see:
• 1a Scriven E, Ramsden CA. Advances in Heterocyclic Chemistry . Academic Press; New York: 2019
• 1b Phillips AM. F. Synthetic Approaches to Nonaromatic Nitrogen Heterocycles, Vol. 1 & 2. Wiley; New York: 2020

For selected reviews, see:
• 1c Candeias NR, Branco LC, Gois PM. P, Afonso CA. M, Trindade AF. Chem. Rev. 2009; 109: 2703
• 1d Taylor AP, Robinson RP, Fobian YM, Blakemore DC, Jones LH, Fadeyi O. Org. Biomol. Chem. 2016; 14: 6611
• 1e Vinogradov MG, Turova OV, Zlotin SG. Org. Biomol. Chem. 2019; 17: 3670
• 1f Gao B, Yang B, Feng X, Li C. Nat. Prod. Rep. 2022; 39: 139

For selected reviews, see:
• 2a Sheng C, Zhang W. Curr. Med. Chem. 2011; 18: 733
• 2b Agalave SG, Maujan SR, Pore VS. Chem. Asian J. 2011; 6: 2696
• 2c El-Sagheer AH, Brown T. Acc. Chem. Res. 2012; 45: 1258
• 2d Thirumurugan P, Matosiuk D, Jozwiak K. Chem. Rev. 2013; 113: 4905
• 2e Bonandi E, Christodoulou MS, Fumagalli G, Perdicchia D, Rastelli G, Passarella D. Drug Discov. Today 2017; 22: 1572
• 3a Lau YH, Rutledge PJ, Watkinson M, Todd MH. Chem. Soc. Rev. 2011; 40: 2848
• 3b Chu C, Liu R. Chem. Soc. Rev. 2011; 40: 2177
• 3c Astruc D, Liang L, Rapakousiou A, Ruiz J. Acc. Chem. Res. 2012; 45: 630
• 3d Xi W, Scott TF, Kloxin CJ, Bowman CN. Adv. Funct. Mater. 2014; 24: 2572
• 4a Bertelli L, Biagi G, Giorgi I, Manera C, Livi O, Scartoni V, Betti L, Giannaccini G, Trincavelli L, Barili PL. Eur. J. Med. Chem. 1998; 33: 113
• 4b Bertelli L, Biagi G, Giorgi I, Livi O, Manera C, Scartoni V, Lucacchini A, Giannaccini G, Barili PL. Eur. J. Med. Chem. 2000; 35: 333
• 4c Abarca B, Ballesteros R, Chadlaoui M, Miralles J, Murillo JV, Colonna D. Tetrahedron 2001; 57: 10111
• 4d Biagi G, Giorgi I, Livi O, Scartoni V, Betti L, Giannaccini G, Trincavelli ML. Eur. J. Med. Chem. 2002; 37: 565
• 4e Lauria A, Patella C, Dattolo G, Almerico AM. J. Med. Chem. 2008; 51: 2037
• 4f Shan Z, Peng M, Fan H, Lu Q, Lu P, Zhao C, Chen Y. Bioorg. Med. Chem. Lett. 2011; 21: 1731
• 4g Ma L.-Y, Pang L.-P, Wang B, Zhang M, Hu B, Xue D.-Q, Shao K.-P, Zhang B.-L, Liu Y, Zhang E, Liu H.-M. Eur. J. Med. Chem. 2014; 86: 368
• 4h Whittaker B, Steele C, Hardick D, Dale M, Pomel V, Quattropani A, Beher D. Eur. Pat. Appl EP 2687528 A1, 2014
• 4i Safari F, Bayat M, Nasri S, Karami S. Bioorg. Med. Chem. Lett. 2020; 30: 127111

For a typical review, see:
• 4j Raić-Malić S, Meščić A. Curr. Med. Chem. 2015; 22: 1462
• 5a Jones P, Chambers M. Tetrahedron 2002; 58: 9973
• 5b Pokhodylo NT, Matiychuk VS. J. Heterocycl. Chem. 2010; 47: 415
• 5c Ivachtchenko AV, Golovina ES, Kadieva MG, Koryakova AG, Kovalenko SM, Mitkin OD, Okun IM, Ravnyeyko IM, Tkachenko SE, Zaremba OV. J. Comb. Chem. 2010; 12: 445
• 5d Qian W, Winternheimer D, Amegadzie A, Allen J. Tetrahedron 2012; 53: 271
• 5e Selvarajua M, Sun C.-M. Adv. Synth. Catal. 2014; 356: 1329
• 5f Kumar KS, Naikawadi PK, Rajesham B, Rambabu D. New J. Chem. 2019; 43: 4333
• 5g Du W, Huang H, Xiao T, Jiang Y. Adv. Synth. Catal. 2020; 362: 5124

Other copper catalysts such as CuI or Cu(OAc)₂ were also evaluated, but the first CuAAC step almost did not happen. For typical reports, see:
• 6a Yoo EJ, Ahlquist M, Kim SH, Bae I, Fokin VV, Sharpless KB, Chang S. Angew. Chem. Int. Ed. 2007; 46: 1730
• 6b Raushel J, Fokin VV. Org. Lett. 2010; 12: 4952

For typical reviews, see:
• 6c Meldal M, Tornøe CW. Chem. Rev. 2008; 108: 2952
• 6d Neto JS. S, Zeni G. Coord. Chem. Rev. 2020; 409: 213217

For selected reviews, see:
• 7a Chattopadhyay B, Gevorgyan V. Angew. Chem. Int. Ed. 2012; 51: 862
• 7b Gulevich AV, Gevorgyan V. Angew. Chem. Int. Ed. 2013; 52: 1371
• 7c Davie HM. L, Alford JS. Chem. Soc. Rev. 2014; 43: 5151
• 7d Wang Y, Lei X, Tang Y. Synlett 2015; 26: 2051

For typical examples, see:
• 8a Jiang Y, Sun R, Wang Q, Tang X.-Y, Shi M. Chem. Commun. 2015; 51: 16968
• 8b Chen K, Zhu Z.-Z, Zhang Y.-S, Tang X.-Y, Shi M. Angew. Chem. Int. Ed. 2014; 53: 6645
• 9a Shi J, Zhu L, Wen J, Chen Z. Chin. J. Catal. 2016; 37: 1222
• 9b Jiang Y, Wang Q, Sun R, Tang X.-Y, Shi M. Org. Chem. Front. 2016; 3: 744
• 9c Ma T, Sun C, Yuan X, Li X, Zhao Z. RSC Adv. 2017; 7: 1062
• 9d Sun C, Yuan X, Li Y, Li X, Zhao Z. Org. Biomol. Chem. 2017; 15: 2721
• 10 Sun R, Zhang DH, Shi M. Synlett 2014; 25: 2293
• 11 Zhou T, Zhu Y, Zhang H, He J, Li H, Lang M, Wang J, Peng S. Adv. Synth. Catal. 2021; 363: 4549
• 12a He M, Chen N, Zhou T, Li Q, Li H, Lang M, Wang J, Peng S. Org. Lett. 2019; 21: 9559
• 12b He M, Chen N, Liu L, Zhu Y, Li Q, Li H, Lang M, Wang J, Peng S. J. Org. Chem. 2020; 85: 4418
• 12c Chen N, Zhou T, Zhang H, Zhu Y, Lang M, Wang J, Peng S. J. Org. Chem. 2021; 86: 4714
• 12d Chen N, He M, Zhou T, Zhu Y, Zhang H, Peng S. Synthesis 2021; 53: 611
• 13 Other enyne substrates bearing N-Ac, N-Boc and N-Ph substituents were not available due to synthetic difficulties.
• 14 Although it is not very clear, the electronic effect of substrates seems to have a significant influence under iron catalysis.
• 15 CCDC 2165165 (4a) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.
• 16 FeCl₃·6H₂O catalyzed version was also performed, but no target product was detected except 4b′ was formed in 16% yield.
• 17 Dong H, Zhang D, Fang R, Du Q, Dong Z, Wei H, Shi M, Wang F. Synth. Commun. 2018; 48: 1227