This review covers all known examples of [3 + 2]-cycloaddition between sydnones and both terminal as well as internal alkynes/cycloalkynes taken from literature since its discovery by Huisgen in 1962 up to the current date. Except enumeration of synthetic applications it also covers mechanistic studies, catalysis, effects of substituents and reaction conditions influencing reaction rate and regioselectivity.

Institute of Organic Chemistry and Technology University of Pardubice Studentská 573 532 10 Pardubice Czech Republic

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Huisgen R, Gotthardt H, Grashey R. Angew Chem, Int Ed Engl. 1962;1:49. doi: 10.1002/anie.196200491. DOI

Huisgen R, Gotthardt H, Grashey R. Chem Ber. 1968;101:536–551. doi: 10.1002/cber.19681010223. DOI

Kolodych S, Rasolofonjatovo E, Chaumontet M, Nevers M-C, Créminon C, Taran F. Angew Chem, Int Ed. 2013;52:12056–12060. doi: 10.1002/anie.201305645. PubMed DOI

Decuypère E, Plougastel L, Audisio D, Taran F. Chem Commun. 2017;53:11515–11527. doi: 10.1039/C7CC06405E. PubMed DOI

Dickopp H. Chem Ber. 1974;107:3036–3042. doi: 10.1002/cber.19741070926. DOI

Badami B V, Puranik G S. Indian J Chem. 1974;12:671–673.

Badami B V, Puranik G S. Can J Chem. 1975;53:913–914. doi: 10.1139/v75-127. DOI

Gotthardt H, Reiter F. Chem Ber. 1979;112:1193–1205. doi: 10.1002/cber.19791120414. DOI

Gotthardt H, Reiter F. Chem Ber. 1981;114:2450–2464. doi: 10.1002/cber.19811140712. DOI

Maffrand J-P. Heterocycles. 1981;16:35–37. doi: 10.3987/R-1981-01-0035. DOI

Dambal D B, Badami B V, Puranik G S. Indian J Chem, Sect B. 1982;21:865–868.

Tikare R K, Badami B V, Puranik G S. Indian J Chem, Sect B. 1983;22:673–677.

Ranganathan D, Bamezai S. Tetrahedron Lett. 1983;24:1067–1070. doi: 10.1016/S0040-4039(00)81606-8. DOI

Havanur S B, Puranik G S. Indian J Chem, Sect B. 1985;24:864–866.

Collibee W L, Anselme J-P. Bull Soc Chim Belg. 1986;95:655–662. doi: 10.1002/bscb.19860950809. DOI

Kano K, Scarpetti D, Warner J C, Anselme J-P, Springer J P, Arison B H. Can J Chem. 1986;64:2211–2219. doi: 10.1139/v86-364. DOI

Badachikar S V, Tikare R K, Puranik G S. Indian J Chem, Sect B. 1986;25:1079–1080.

Kalinin V N, Min S F. Bull Acad Sci USSR, Div Chem Sci (Engl Transl) 1988;37:762–764. doi: 10.1007/BF01455497. DOI

Sakamoto T, Shiga F, Uchiyama D, Kondo Y. Heterocycles. 1992;33:813–818. doi: 10.3987/COM-91-S87. DOI

Dumitraşcu F, Drăghici C, Dumitrescu D, Tarko L, Răileanu D. Liebigs Ann/Recl. 1997:2613–2616. doi: 10.1002/jlac.199719971229. DOI

Dumitraşcu F, Drăghici C, Căproiu M, Crangus C, Mitan C I, Barbu L, Răileanu D. Rev Chim (Bucharest, Rom) 2001;52:183–187.

Dumitraşcu F, Mitan C I, Dumitrescu D, Drăghici C, Căproiu M T. ARKIVOC. 2002;(ii):80–86. doi: 10.3998/ark.5550190.0003.209. DOI

Dumitraşcu F, Mitan C I, Drăghici C, Barbu L, Căproiu M T A. Univ Bucuresti, Chim. 2002;11:237–242.

Dumitraşcu F, Drăghici C, Crangus C, Căproiu M, Mitan C I, Dumitrescu D, Răileanu D. Rev Roum Chim. 2002;47:315–318.

Dumitraşcu F, Mitan C I, Dumitrescu D, Barbu L, Hrubaru M, Caprau D, Vuluga D. Rev Chim (Bucharest, Rom) 2003;54:747–751.

Chang E-M, Lin C-J, Wong F F, Yeh M-Y. Heterocycles. 2006;68:733–748. doi: 10.3987/COM-06-10699. DOI

Sanyal R, Badami B V. J Heterocycl Chem. 2006;43:827–834. doi: 10.1002/jhet.5570430403. DOI

Dumitraşcu F, Drăghici C, Vuluga D, Căproiu M T. Rev Roum Chim. 2006;51:255–260.

Chang E-M, Lee C-T, Chen C-Y, Wong F F, Yeh M-Y. Aust J Chem. 2008;61:342–349. doi: 10.1071/CH07381. DOI

Rodriguez A, Moran W J. Synthesis. 2009:650–654. doi: 10.1055/s-0028-1083344. DOI

Chang E-M, Huang S-L, Lee C-T, Lin H-C, Chen C-Y, Huang Y-Y, Lin S-K, Wong F F. Aust J Chem. 2009;62:1355–1362. doi: 10.1071/CH08344. DOI

Foster R S, Jakobi H, Harrity J P A. Org Lett. 2012;14:4858–4861. doi: 10.1021/ol3021918. PubMed DOI

Foster R S, Adams H, Jakobi H, Harrity J P A. J Org Chem. 2013;78:4049–4064. doi: 10.1021/jo400381a. PubMed DOI

Nassoy A-C, Raubo P, Harrity J P A. Tetrahedron Lett. 2013;54:3094–3096. doi: 10.1016/j.tetlet.2013.03.139. DOI

Wang L-Y, Chang E-C, Yeh M-Y, Chung Y H, Huang J-J, Wong F F. Heteroat Chem. 2014;25:171–177. doi: 10.1002/hc.21151. DOI

Lopes S M M, Correia C F O, Nunes S C C, Pereira N A M, Ferreira A R F, Sousa E P, Gomes C S B, Salvador J A R, Pais A A C C, Pinho e Melo T M V D. Org Biomol Chem. 2015;13:9127–9139. doi: 10.1039/C5OB01110H. PubMed DOI

Badami B V, Puranik G S. Rev Roum Chim. 1982;27:281–284.

Gotthardt H, Böhm F-R, Brauer D J, Weisshuhn C M, Wilke C J. Chem Ber. 1988;121:95–104. doi: 10.1002/cber.19881210115. DOI

Rao H S P, Barthasarathy N. Indian J Heterocycl Chem. 2007;16:413–414.

Li J, Wu F, Liu X, Zou Y, Chen H, Li Z, Zhang L. Eur J Med Chem. 2017;140:20–30. doi: 10.1016/j.ejmech.2017.08.047. PubMed DOI

McGowin A E, Jackson L, Marshall L W, Tumbull K. Org Prep Proced Int. 2001;33:100–102. doi: 10.1080/00304940109356581. DOI

Wallace S, Chin J W. Chem Sci. 2014;5:1742–1744. doi: 10.1039/C3SC53332H. PubMed DOI PMC

Plougastel L, Koniev O, Specklin S, Decuypere E, Créminon C, Buisson D-A, Wagner A, Kolodych S, Taran F. Chem Commun. 2014;50:9376–9378. doi: 10.1039/C4CC03816A. PubMed DOI

Liu H, Audisio D, Plougastel L, Decuypere E, Buisson D-A, Koniev O, Kolodych S, Wagner A, Elhabiri M, Krzyczmonik A, et al. Angew Chem, Int Ed. 2016;55:12073–12077. doi: 10.1002/anie.201606495. PubMed DOI

Narayanam M K, Liang Y, Houk K N, Murphy J M. Chem Sci. 2016;7:1257–1261. doi: 10.1039/C5SC03259H. PubMed DOI PMC

Liu F, Liang Y, Houk K N. Acc Chem Res. 2017;50:2297–2308. doi: 10.1021/acs.accounts.7b00265. PubMed DOI PMC

Medina J M, McMahon T C, Jiménez-Osés G, Houk K N, Garg N K. J Am Chem Soc. 2014;136:14706–14709. doi: 10.1021/ja508635v. PubMed DOI PMC

Lazaris A Y. Zh Org Khim. 1966;2:1322–1323.

Wu C, Fang Y, Larock R C, Shi F. Org Lett. 2010;12:2234–2237. doi: 10.1021/ol100586r. PubMed DOI PMC

Fang Y, Wu C, Larock R C, Shi F. J Org Chem. 2011;76:8840–8851. doi: 10.1021/jo201605v. PubMed DOI PMC

Seliverstov M Y, Afanas'ev O I, Sosonyuk S E, Temnov V V, Proskurnina M V, Zefirova N S. Dokl Chem. 2016;466:41–44. doi: 10.1134/S0012500816020063. DOI

Li L, Wang H, Yang X, Kong L, Wang F, Li X. J Org Chem. 2016;81:12038–12045. doi: 10.1021/acs.joc.6b02356. PubMed DOI

Ikawa T, Masuda S, Nakajima H, Akai S. J Org Chem. 2017;82:4242–4253. doi: 10.1021/acs.joc.7b00238. PubMed DOI

Huisgen R, Gotthardt H. Chem Ber. 1968;101:1059–1071. doi: 10.1002/cber.19681010343. DOI

Youn B H, Lyu H S, Han J H, Kim S H. Bull Korean Chem Soc. 1987;8:233–235.

Hoffmann R, Woodward R B. J Am Chem Soc. 1965;87:2046–2048. doi: 10.1021/ja01087a034. DOI

Sustmann R. Pure Appl Chem. 1974;40:569–593. doi: 10.1351/pac197440040569. DOI

Houk K N, Sims J, Duke R E, Jr, Strozier R W, George J K. J Am Chem Soc. 1973;95:7287–7301. doi: 10.1021/ja00803a017. DOI

Krauch C H, Kuhls J, Piek H-J. Tetrahedron Lett. 1966;7:4043–4048. doi: 10.1016/S0040-4039(00)90284-3. DOI

Huseya Y, Chinone A, Ohta M. Bull Chem Soc Jpn. 1971;44:1667–1668. doi: 10.1246/bcsj.44.1667. DOI

Chinone A, Huseya Y, Ohta M. Bull Chem Soc Jpn. 1970;43:2650. doi: 10.1246/bcsj.43.2650. DOI

George M V, Angadiyavar C S. J Org Chem. 1971;36:1589–1594. doi: 10.1021/jo00811a004. DOI

Gotthardt H, Reiter F. Tetrahedron Lett. 1971:2749–2752. doi: 10.1016/S0040-4039(01)96970-9. DOI

Gotthardt H, Reiter F. Chem Ber. 1979;112:1206–1225. doi: 10.1002/cber.19791120415. DOI

Märky M, Hansen H-J, Schmid H. Helv Chim Acta. 1971;54:1275–1278. doi: 10.1002/hlca.19710540506. DOI

Sasaki T, Kanematsu K. J Chem Soc C. 1971:2147–2150. doi: 10.1039/j39710002147. DOI

Kishimoto S, Noguchi S, Masuda K. Chem Pharm Bull. 1976;24:3001–3010. doi: 10.1248/cpb.24.3001. PubMed DOI

Croce P D, La Rosa C, Zecchi G. J Chem Soc, Perkin Trans 1. 1985:2621–2624. doi: 10.1039/p19850002621. DOI

Ranganathan D, Bamezai S. Synth Commun. 1985;15:259–265. doi: 10.1080/00397918508063796. DOI

Jeon D J, Lee J N, Kim H R, Ryu E K. Bull Korean Chem Soc. 1998;19:725–726.

Lee J N, Jeon D J, Kim Y M, Kim K M, Song H S. Bull Korean Chem Soc. 2000;21:761–762.

Venkatesan A M, Mansour T S, Abe T, Yamamura I, Takasaki T, Agarwal A, Dos Santos O, Sum F-W, Lin Y-I, inventors. Bicyclic 6-alkylidene-penems as ß-lactamases inhibitors. WO 2003093279 A1. WO Patent. 2003 Nov 13;

Abe T, Matsunaga H, Mihira A, Sato C, Ushirogochi H, Sato K, Takasaki T, Venkatesan A M, Mansour T S, inventors. Process for preparing 6-alkylidene penem derivatives. WO 2003093277 A1. WO Patent. 2003 Nov 13;

Nikitenko A A, Winkley M W, Zeldis J, Kremer K, Chan A W-Y, Strong H, Jennings M, Jirkovský I, Blum D, Khafizova G, et al. Org Process Res Dev. 2006;10:712–716. doi: 10.1021/op050218b. DOI

Chang E-M, Wong F F, Chen T-H, Chiang K-C, Yeh M-Y. Heterocycles. 2006;68:1007–1015. doi: 10.3987/COM-06-10714. DOI

Chang E-M, Chen T-H, Wong F F, Chang E-C, Yeh M-Y. Synlett. 2006:901–904. doi: 10.1055/s-2006-939041. DOI

Venkatesan A M, Agarwal A, Abe T, Ushirogochi H, Yamamura I, Ado M, Tsuyoshi T, Dos Santos O, Gu Y, Sum F-W, et al. J Med Chem. 2006;49:4623–4637. doi: 10.1021/jm060021p. PubMed DOI

González-Nogal A M, Calle M, Cuadrado P, Valero R. Tetrahedron. 2007;63:224–231. doi: 10.1016/j.tet.2006.10.026. DOI

Browne D L, Helm M D, Plant A, Harrity J P A. Angew Chem, Int Ed. 2007;46:8656–8658. doi: 10.1002/anie.200703767. PubMed DOI

Browne D L, Taylor J B, Plant A, Harrity J P A. J Org Chem. 2009;74:396–400. doi: 10.1021/jo802240e. PubMed DOI

Browne D L, Vivat J F, Plant A, Gomez-Bengoa E, Harrity J P A. J Am Chem Soc. 2009;131:7762–7769. doi: 10.1021/ja902460n. PubMed DOI

Browne D L, Taylor J B, Plant A, Harrity J P A. J Org Chem. 2010;75:984–987. doi: 10.1021/jo902514v. PubMed DOI

Carceller Gonzalez E, Virgili Bernado M, inventors. 2H-Pyrazolo[4,3-d]pyrimidin-5-amine derivatives as H4 Histamine receptor antagonists for the treatment of allergic, immunological and inflamatory diseases. WO 2010043633 A1. WO Patent. 2010 Apr 22;

Foster R S, Jakobi H, Harrity J P A. Tetrahedron Lett. 2011;52:1506–1508. doi: 10.1016/j.tetlet.2011.01.115. DOI

Mattes A, Helmke H, Hillebrand S, Peris G, Sudau A, Rodefeld L, Gauger S, Benting J, Dahmen P, Meissner R, et al., inventors. Bicyclic pyrimidinyl pyrazoles. WO 2011124539 A1. WO Patent. 2011 Oct 13;

Dürüst Y, Sağırlı A, Kariuki B M, Knight D W. Tetrahedron. 2014;70:6012–6019. doi: 10.1016/j.tet.2014.04.083. DOI

Chappie T A, Helal C J, Kormos B L, Tuttle J B, Verhoest P R, inventors. Imidazo-triazine derivatives as PDE10 inhibitors. WO 2014177977 A1. WO Patent. 2014 Nov 6;

Handa N V, Li S, Gerbec J A, Sumitani N, Hawker C J, Klinger D. J Am Chem Soc. 2016;138:6400–6403. doi: 10.1021/jacs.6b03381. PubMed DOI

Brown A W, Fisher M, Tozer G M, Kanthou C, Harrity J P A. J Med Chem. 2016;59:9473–9488. doi: 10.1021/acs.jmedchem.6b01128. PubMed DOI

Brown A W, Harrity J P A. J Org Chem. 2015;80:2467–2472. doi: 10.1021/acs.joc.5b00143. PubMed DOI

Brown A W, Harrity J P A. Tetrahedron. 2017;73:3160–3172. doi: 10.1016/j.tet.2017.04.049. DOI

Comas-Barceló J, Foster R S, Fiser B, Gomez-Bengoa E, Harrity J P A. Chem – Eur J. 2015;21:3257–3263. doi: 10.1002/chem.201406118. PubMed DOI

Totoe H, McGowin A E, Turnbull K. J Supercrit Fluids. 2000;18:131–140. doi: 10.1016/S0896-8446(00)00060-7. DOI

Houk K N, Sims J, Watts C R, Luskus L J. J Am Chem Soc. 1973;95:7301–7315. doi: 10.1021/ja00803a018. DOI

Huppatz J L. Aust J Chem. 1983;36:135–147. doi: 10.1071/CH9830135. DOI

Bernard A, Cocco M T, Maccioni A, Plumitallo A. Farmaco, Ed Sci. 1985;40:259–271.

Ranganathan D, Bamezai S, Cun-Heng H, Clardy J. Tetrahedron Lett. 1985;26:5739–5742. doi: 10.1016/S0040-4039(00)98912-3. DOI

Ranganathan D, Bamezai S, Saini S. Indian J Chem, Sect B. 1991;30:169–175.

Fariňa F, Fernández P, Fraile T, Martín V M, Martín M R. Heterocycles. 1989;29:967–974. doi: 10.3987/COM-89-4930. DOI

Meazza G, Zanardi G, Piccardi P. J Heterocycl Chem. 1993;30:365–371. doi: 10.1002/jhet.5570300213. DOI

Chan D M-T, Kamireddy B, Kim H B, Patel K M, Sharpe P L, Casini M S, Xu M, Armel G R, Stevenson T M, inventors. Azolecarboxamide herbicides. WO 2004106324 A1. WO Patent. 2004 Dec 9;

Rai G, Puranik V G, Kalluraya B, Hegde J C. Synth Commun. 2006;36:1285–1290. doi: 10.1080/00397910500518874. DOI

Plant A, Boehmer J E, Black J, Sparks T D, inventors. Isoxazoline derivatives and their use as herbicides. WO 2006024820 A1. WO Patent. 2006 Mar 9;

Satheesha Rai N, Kalluraya B. Indian J Chem, Sect B. 2007;46:375–378.

Satheesha Rai N, Kalluraya B, Lingappa B, Shenoy S, Puranic V G. Eur J Med Chem. 2008;43:1715–1720. doi: 10.1016/j.ejmech.2007.08.002. PubMed DOI

Gao D, Zhai H, Parvez M, Back T G. J Org Chem. 2008;73:8057–8068. doi: 10.1021/jo801621d. PubMed DOI

Foster R S, Huang J, Vivat J F, Browne D L, Harrity J P A. Org Biomol Chem. 2009;7:4052–4056. doi: 10.1039/b910632d. PubMed DOI

Bisaha J J, Crews A D Jr, Howard M H Jr, Sharpe P L, Stevenson T M, Taggi A E, inventors. Fungicidal bicyclic pyrazoles. WO 2009076440 A2. WO Patent. 2009 Jun 18;

Stevenson T M, Marshall E A, Taggi A E, inventors. Herbicidal pyridazinone derivatives. WO 2009086041 A1. 2009 Jul 9;

Delaunay T, Es-Sayed M, Vors J-P, Monteiro N, Balme G. Eur J Org Chem. 2011:3837–3848. doi: 10.1002/ejoc.201100119. DOI

Chang E-C, Wen Y-L, Chang C-H, Shen Y-H, Wen S-B, Yeh M-Y, Wong F F. Tetrahedron. 2012;68:5920–5924. doi: 10.1016/j.tet.2012.04.093. DOI

Brown A W, Comas-Barceló J, Harrity J P A. Chem – Eur J. 2017;23:5228–5231. doi: 10.1002/chem.201701019. PubMed DOI

Shi J, Xu H, Qiu D, He J, Li Y. J Am Chem Soc. 2017;139:623–626. doi: 10.1021/jacs.6b12161. PubMed DOI

Ikawa T, Masuda S, Takagi A, Akai S. Chem Sci. 2016;7:5206–5211. doi: 10.1039/C6SC00798H. PubMed DOI PMC

Shah T K, Medina J M, Garg N K. J Am Chem Soc. 2016;138:4948–4954. doi: 10.1021/jacs.6b01986. PubMed DOI PMC

Wezeman T, Comas-Barceló J, Nieger M, Harrity J P A, Bräse S. Org Biomol Chem. 2017;15:1575–1579. doi: 10.1039/C6OB02518H. PubMed DOI

Lallana E, Riguera R, Fernandez-Megia E. Angew Chem, Int Ed. 2011;50:8794–8804. doi: 10.1002/anie.201101019. PubMed DOI

Specklin S, Decuypere E, Plougastel L, Aliani S, Taran F. J Org Chem. 2014;79:7772–7777. doi: 10.1021/jo501420r. PubMed DOI

Decuypere E, Specklin S, Gabillet S, Audisio D, Liu H, Plougastel L, Kolodych S, Taran F. Org Lett. 2015;17:362–365. doi: 10.1021/ol503482a. PubMed DOI

Taran F, Chaumontet M, Kolodych S, Rasolofonjatovo Andovola E, inventors. Method for producing pyrazoles, novel pyrazoles and application thereof. WO2014122407 A2. WO Patent. 2014 Aug 14;

Comas-Barceló J, Harrity J P A. Synthesis. 2017;49:1168–1181. doi: 10.1055/s-0036-1588922. DOI

Adeleke A F, Brown A P N, Cheng L-J, Mosleh K A M, Cordier C J. Synthesis. 2017;49:790–801. doi: 10.1055/s-0036-1588405. DOI

Worrell B T, Malik J A, Fokin V V. Science. 2013;340:457–460. doi: 10.1126/science.1229506. PubMed DOI PMC

Conry R R. Copper: Inorganic & Coordination Chemistry. Encyclopedia of Inorganic Chemistry. John Wiley & Sons, Ltd.; 2006.

Pallenberg A J, Koenig K S, Barnhart D M. Inorg Chem. 1995;34:2833–2840. doi: 10.1021/ic00115a009. DOI

Nitsch J, Kleeberg C, Fröhlich R, Steffen A. Dalton Trans. 2015;44:6944–6960. doi: 10.1039/C4DT03706E. PubMed DOI

Comas-Barceló J, Blanco-Ania D, van den Broek S A M W, Niuwland P J, Harrity J P A, Rutjes F P J T. Catal Sci Technol. 2016;6:4718–4723. doi: 10.1039/C5CY02247A. DOI