Synthesis of Diethoxy Arylphosphoryl Functionalized, Fully Substituted 5-Triazenyl-1,2,3-triazoles via Chelation-Assisted Interrupted Domino Reaction of ortho-Azidophosphonates with Copper(I) Alkynes

Abstract

We describe the synthesis of 1,4-disubstituted 5-triazenyl-1,2,3-triazoles bearing diethoxy arylphosphoryl moieties via a domino reaction between ortho-azidophosphonates and premade copper(I) alkynides involving chelation-assisted [3+2] cycloaddition followed by interception of the copper(I) triazolide generated by the azide. A resulting dicopper(I) triazoletriazenide complex has been characterized through X-ray diffraction.

Key words

ortho-azidophosphonates - copper(I) alkynes - domino reaction - 1,2,3-triazoles - chelation - interrupted click reaction

• References

• 1 Kalra P, Kaur R, Singh G, Singh H, Singh G, Pawan, Kaur G, Singh J. , J. Organomet. Chem. 2021; 944: 121846
• 2a Struthers H, Mindt TL, Schibli R. Dalton Trans. 2010; 39: 675
• 2b Aromía G, Barriosa LA, Roubeaub O, Gameza P. Coord. Chem. Rev. 2011; 255: 485
• 2c Zurro M, Mancheño OG. Chem. Rec. 2017; 17: 485
• 2d Hosseinnejad T, Ebrahimpour-Malmir F, Fattahi B. RSC Adv. 2018; 8: 12232
• 2e Seifert TP, Bestgen S, Feuerstein TJ, Lebedkin S, Krämer F, Fengler C, Gamer MT, Kappes MM, Roesky PW. Dalton Trans. 2019; 48: 15427
• 3a Wang Y, Xing S.-H, Bai F.-Y, Xing Y.-H, Sun L.-X. Inorg. Chem. 2018; 57: 12850
• 3b Li JX, Guan QL, Wang Y, You ZX, Xing YH, Bai FY, Sun LX. New J. Chem. 2020; 44: 1446
• 4a Soltis MJ, Yeh HJ, Cole KA, Whittaker N, Wersto RP, Kohn EC. Drug Metab. Dispos. 1996; 24: 799
• 4b Morzherin Y, Prokhorova PE, Musikhin DA, Glukhareva TV, Fan Z. Pure Appl. Chem. 2011; 83: 715
• 4c De Simone R, Chini MG, Bruno I, Riccio R, Mueller D, Werz O, Bifulco G. J. Med. Chem. 2011; 54: 1565
• 4d Wales SM, Hammer KA, King AM, Tague AJ, Lyras D, Riley TV, Keller PA, Pyne SG. Org. Biomol. Chem. 2015; 13: 5743
• 4e Devender N, Gunjan S, Chhabra S, Singh K, Pasam VR, Shukla SK, Sharma A, Jaiswal S, Singh SK, Kumar Y, Lal J, Trivedi AK, Tripathi R, Tripathi RP. Eur. J. Med. Chem. 2016; 109: 187
• 4f Parvizi J, Mahmoodi NO, Pirbasti FG, Rassa M. ChemistrySelect 2019; 4: 5421
• 4g Ashour HF, Abou-zeid LA, El-Sayed MA.-A, Selim KB. Eur. J. Med. Chem. 2020; 189: 112062
• 4h Gomes CB, Balaguez RA, Larroza A, Smaniotto TA, Domingues M, Casaril AM, Silva MS, Rodrigues OE. D, Savegnago L, Alves D. ChemistrySelect 2020; 5: 12255
• 5a Elliott PI. P. Organometallic Complexes with 1,2,3-Triazole-Derived Ligands . In Organometallic Chemistry, Vol. 39. Fairlamb IJ. S, Lynam JM. RSC Publishing; Cambridge: 2014: 1-25
• 5b Mondal D, Balakrishna MS. Eur. J. Inorg. Chem. 2020; 2392
• 6a Liu D, Gao W, Dai Q, Zhang X. Org. Lett. 2005; 7: 4907
• 6b Oura I, Shimizu K, Ogata K, Fukuzawa S.-I. Org. Lett. 2010; 12: 1752
• 7 Zink DM, Grab T, Baumann T, Nieger M, Barnes EC, Klopper W, Bräse S. Organometallics 2011; 30: 3275
• 8 Chen Z, Liu Z, Cao G, Li H, Ren H. Adv. Synth. Catal. 2017; 359: 202
• 9 Cai Q, Yan J, Ding K. Org. Lett. 2012; 14: 3332
• 10a Zhang Z, Zhou Q, Ye F, Xia Y, Wu G, Hossain ML, Zhang Y, Wang J. Adv. Synth. Catal. 2015; 357: 2277
• 10b Wang W, Peng X, Wei F, Tung C.-H, Xu Z. Angew. Chem. Int. Ed. 2016; 55: 649
• 10c Xu J, Song Q. Org. Chem. Front. 2017; 4: 938
• 10d Wei F, Zhou T, Ma Y, Tung C.-H, Xu Z. Org. Lett. 2017; 19: 2098
• 10e Zhang Z, Zhou Q, Yu W, Li T, Zhang Y, Wang J. Chin. J. Chem. 2017; 35: 387
• 10f Pak K, Cheung S, Tsui GC. Org. Lett. 2017; 19: 2881
• 10g Wang W, Lin Y, Ma Y, Tung C.-H, Xu Z. Org. Lett. 2018; 20: 2956
• 10h Zhu A, Xing X, Wang S, Yuan D, Zhu G, Geng M, Guo Y, Zhang G, Li L. Green Chem. 2019; 21: 3407
• 10i Zhang L.-L, Li Y.-T, Gao T, Guo S.-S, Yang B, Meng Z.-H, Dai Q.-P, Xu Z.-B, Wu Q.-P. Synthesis 2019; 51: 4170
• 10j Larin EM, Lautens M. Angew. Chem. Int. Ed. 2019; 58: 13438
• 11a Selvaraju M, Sun C.-M. Adv. Synth. Catal. 2014; 356: 1329
• 11b Wang W, Huang S, Yan S, Sun X, Tung C.-H, Xu Z. Chin. J. Chem. 2020; 38: 445
• 12a Sun H, Huang Y. Synlett 2015; 26: 2751
• 12b Dong W, Chen Z, Xu J, Miao M, Ren H. Synlett 2016; 27: 1318
• 12c Francisco AP, Mendes E, Santos AR, Perry MJ. Curr. Pharm. Des. 2019; 25: 1623
• 13 Shealy YF, O’Dell CA. J. Med. Chem. 1966; 9: 733
• 14a Akimova GS, Chistokletov VN, Petrov AA. Zh. Org. Khim. 1968; 4: 389
• 14b Olsen CK. Acta Chem. Scand. 1973; 27: 1987
• 15 Zeng L, Lai Z, Zhang C, Xie H, Cui S. Org. Lett. 2020; 22: 2220
• 16 Navarro Y, García-López J, Iglesias MJ, López-Ortiz F. Org. Lett. 2021; 23: 334
• 17a Wang B, Liu N, Shao C, Zhang Q, Wang X, Hu Y. Adv. Synth. Catal. 2013; 355: 2564
• 17b Wang B, Zhang J, Wang X, Liu N, Chen W, Hu Y. J. Org. Chem. 2013; 78: 10519
• 17c Wang B, Ahmed MN, Zhang J, Chen W, Wang X, Hu Y. Tetrahedron Lett. 2013; 54: 6097
• 17d Wang B, Liu N, Chen W, Huang D, Wang X, Hu Y. Adv. Synth. Catal. 2015; 357: 401
• 17e Wang X, Wang X, Wang X, Zhang J, Liu C, Hu Y. Chem. Rec. 2017; 17: 1231
• 18 Demmer CS, Krogsgaard-Larsen N, Bunch L. Chem. Rev. 2011; 111: 7981
• 19a Kee J.-M, Villani B, Carpenter LR, Muir TW. J. Am. Chem. Soc. 2010; 132: 14327
• 19b Mukai S, Flematti GR, Byrne LT, Besant PG, Attwood PV, Piggott MJ. Amino Acids 2012; 43: 857
• 20 Radi S, Lazrek HB. J. Chem. Res., Synop. 2002; 264
• 21a Li L, Hao G, Zhu A, Fan X, Zhang G, Zhang L. Chem. Eur. J. 2013; 19: 14403
• 21b Lv M, Wang M, Lu K, Peng L, Zhao Y. Phosphorus, Sulfur Silicon Relat. Elem. 2018; 193: 206
• 21c Tripolszky A, Németh K, Szabó PT, Bálint E. Molecules 2019; 24: 2085
• 22 Bessmertnykh A, Douaihy CM, Guilard R. Chem. Lett. 2009; 38: 738
• 23 Jouvin K, Heimburger J, Evano G. Chem. Sci. 2012; 3: 756
• 24 Yi K, Li C.-J, Li J, Jia X.-S. Appl. Organomet. Chem. 2011; 25: 16
• 25 Pokhodylo NT, Tupuchak MA, Shyyka OYa, Obushak MD. Russ. J. Org. Chem. 2019; 55: 1310
• 26 Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
• 27 Angell Y, Burgess K. Angew. Chem. Int. Ed. 2007; 46: 3649
• 28 Zheng Z.-J, Wang D, Xu Z, Xu L.-W. Beilstein J. Org. Chem. 2015; 11: 2557
• 29a Laborde C, Wei M.-M, van der Lee A, Deydier E, Daran J.-C, Volle J.-N, Poli R, Pirat J.-L, Manoury E, Virieux D. Dalton Trans. 2015; 44: 12539
• 29b Etayo P, Escudero-Adán EC, Pericàs MA. Catal. Sci. Technol. 2017; 7: 4830
• 29c Sevrain N, Volle J.-N, Pirat J.-L, Ayad T, Virieux D. RSC Adv. 2017; 7: 52101
• 29d Sevrain N, Volle J.-N, Pirat J.-L, Ayad T, Virieux D. Eur. J. Org. Chem. 2018; 2267
• 30 Brassard CJ, Zhang X, Brewer CR, Liu P, Clark RJ, Zhu L. J. Org. Chem. 2016; 81: 12091
• 31 CCDC 2094506 (21b) and 2094505 (24) contain 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
• 32 APEX3 v2014.5-0 . Bruker AXS Inc; Madison (WI, USA): 2014
• 33 SAINT V8.38A . Bruker AXS Inc; Madison (WI, USA): 2017
• 34 SADABS . Bruker AXS Inc; Madison (WI, USA): 2016
• 35 Betteridge PW, Carruthers JR, Cooper RI, Prout K, Watkin DJ. J. Appl. Crystallogr. 2003; 36: 1487
• 36 Sheldrick GM. Acta Crystallogr., Sect. A 2008; 64: 112
• 37 Farrugia LJ. J. Appl. Crystallogr. 2012; 45: 849
• 38 Legault CY. CYLview, 1.0b. Université de Sherbrooke; Canada: 2009. (accessed Aug 30, 2021), http://www.cylview.org
• 39 Kyba EP, Clubb CN. Inorg. Chem. 1984; 23: 4766
• 40 Hu J, Cheng Y, Yang Y, Rao Y. Chem. Commun. 2011; 47: 10133