Subscribe to RSS
DOI: 10.1055/s-0040-1707355
Recent Advances in Cycloaddition Reactions with Alkynes to Construct Heterocycles
This research was supported by the National Natural Science Foundation of China (Nos. 21625203 and 21871126).
Abstract
Heterocyclic compounds, especially N-heterocycles and O-heterocycles, are prominent structural motifs present in numerous natural products and medically and/or economically important compounds. This review aims to describe the development of transition-metal-catalyzed cycloaddition reactions of functionalized m-atom partners with alkynes to access a wide range of five-, six-, and seven-membered heterocycles, that is functionalized N-heterocycles and O-heterocycles such as azepines, isoquinolines, isocoumarins, spiroheterocycles, indoles, furans, and pyrroles, in a selectively controlled manner with an emphasis on scope and limitations and with a discussion of the mechanisms.
1 Introduction
2 Intermolecular Cycloaddition To Construct Azepine Derivatives
2.1 [5+2] Cycloaddition
2.2 [3+2+2] Cycloaddition
2.3 [3+2]/[5+2] Cycloaddition
3 Intermolecular [4+2] Cycloaddition To Construct Isoquinolines or Isocoumarins
4 Intermolecular [3+2] Cycloaddition To Construct Spiroheterocyclic Compounds, Indoles, Furans, and Pyrroles
5 Summary and Outlook
Publication History
Received: 30 April 2020
Accepted: 24 July 2020
Article published online:
13 October 2020
© 2020. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Kametani T, Fukumoto K. Heterocycles 1975; 3: 931
- 1b Heterocyclic Compounds: Azepines . Renfroe B, Harrington C, Proctor GR. Wiley Interscience; New York: 1984
- 1c Dictionary of Pharmacological Agents . Ganellin CR, Triggle DJ. Chapman & Hall/CRC; London: 1996
- 1d Kulanthaivel P, Hallock YF, Boros C, Hamilton SM, Janzen WP, Ballas LM, Loomis CR, Jiang JB, Katz B, Steiner JR, Clardy J. J. Am. Chem. Soc. 1993; 115: 6452
- 1e Freidinger RM, Verber DF, Perlow DS, Brooks JR, Saperstein R. Science 1980; 210: 656
- 1f The Alkaloids, Vol. 9. Götz M, Edwards OE, Manske RH. F. Academic Press; New York: 1967: 545
- 1g Ye Y, Qin G.-W, Xu R.-S. Phytochemistry 1994; 37: 1205
- 1h Hu J, Miller MJ. Tetrahedron Lett. 1995; 36: 6379
- 1i Song Y.-F, Qu Y, Cao X.-P, Zhang W. Mar. Biotechnol. 2011; 13: 868
- 1j Villani FJ. J. Med. Chem. 1967; 10: 497
- 1k Gijsen HJ. M, Berthelot D, Zaja M, Brône B, Geuens I, Mercken M. J. Med. Chem. 2010; 53: 7011
- 1l Tomasi S, Renault J, Martin B, Duhieu S, Cerec V, Roch ML, Uriac P, Delcros J.-G. J. Med. Chem. 2010; 53: 7647
-
2a Hepatitis c virus (HCV) inhibitors:
Zhang Y,
Zhang J,
Xie H,
Ren Q,
Wu X,
Luo H,
Fu C,
Hu B,
Li S,
Tang C,
Lei Y,
Yu Q,
Fang Q,
Qang C.
WO 2014048072A1, 2014
-
2b Inhibitors of beta-secretase:
Dillard LW,
Yuan J,
Leftheris K,
Venkatraman S,
Wu G,
Jia L,
Xu Z,
Cacatian S,
Morales-Ramos A,
Singh S,
Zheng Y.
WO 2011106414A1, 2011
- 2c Ullrich T, Krich S, Binder D, Mereiter K, Anderson DJ, Meyer MD, Pyerin M. J. Med. Chem. 2002; 45: 4047
-
2d Herbicidal action:
Waespe HS. R,
Guy RE,
Van L,
Sipido VK.
WO 9209577A1, 1992
- 2e Kantarjian HM, Talpaz M, Santini V, Murgo A, Cheson B, O’Brien SM. Cancer 2001; 92: 1591
- 2f Levy V, Zohar S, Bardin C, Vekhoff A, Chaoui D, Rio B, Legrand O, Sentenac S, Rousselot P, Raffoux E, Chast F, Chevret S, Marie JP. Br. J. Cancer 2006; 95: 253
- 2g Sacchi S, Kantarjian HM, O’Brien S, Cortes J, Rios MB, Giles FJ, Beran M, Koller CA, Keating MJ, Talpaz M. Cancer 1999; 86: 2632
- 2h Shifrin VI, Anderson P. J. Biol. Chem. 1999; 274: 13985
- 3a Advances in Cycloaddition, Vols. 1–6. JAI Press; Greenwich: 1988
- 3b Schore NE. Chem. Rev. 1988; 88: 1081
- 3c Cycloaddition Reactions in Organic Synthesis. Carruthers W. Pergamon; Oxford: 1990
- 3d Lautens M, Klute W, Tam W. Chem. Rev. 1996; 96: 49
- 3e Yet L. Chem. Rev. 2000; 100: 2963
- 3f Cycloaddition Reactions in Organic Synthesis . Kobayashi S, Jørgensen KA. Wiley-VCH; Weinheim: 2002
- 3g Methods and Applications of Cycloaddition Reactions in Organic Syntheses. Nishiwaki N. Wiley-VCH; Hoboken: 2014
- 3h Heller B, Hapke M. Chem. Soc. Rev. 2007; 36: 1085
- 3i Dyker G. Angew. Chem. Int. Ed. Engl. 1995; 34: 2223
- 3j Battiste MA, Pelphrey PM, Wright DL. Chem. Eur. J. 2006; 12: 3438
- 3k Butenschön H. Angew. Chem. Int. Ed. 2008; 47: 5287
- 3l Lohse AG, Hsung RP. Chem. Eur. J. 2011; 17: 3812
- 3m Pellissier H. Adv. Synth. Catal. 2011; 353: 189
- 3n Ylijoki KE. O, Stryker JM. Chem. Rev. 2013; 113: 2244
- 3o Feng J.-J, Zhang J. ACS Catal. 2016; 6: 6651
- 3p Pellissier H. Adv. Synth. Catal. 2018; 360: 1551
- 3q Gao K, Zhang Y.-G, Wang ZG, Ding H. Chem. Commun. 2019; 55: 1859
- 4a Stogryn EL, Brois SJ. J. Am. Chem. Soc. 1967; 89: 605
- 4b Hassner A, Costa RD, McPhail AT, Butler W. Tetrahedron Lett. 1981; 22: 3691
- 5a Wender PA, Pedersen TM, Scanio MJ. C. J. Am. Chem. Soc. 2002; 124: 15154
- 5b Montero-Campillo MM, Cabaleiro-Lago EM, Rodríguez-Otero J. J. Phys. Chem. A 2008; 112: 9068
- 6 Zhou M.-B, Song R.-J, Wang C.-Y, Li J.-H. Angew. Chem. Int. Ed. 2013; 52: 10805
- 7 Kunkely H, Vogler A. Inorg. Chem. Commun. 2004; 7: 400
- 8 Hu C, Song R.-J, Hu M, Yang Y, Li J.-H, Luo SL. Angew. Chem. Int. Ed. 2016; 55: 10423
- 9 Zhou M.-B, Pi R, Teng F, Li Y, Li J.-H. Chem. Commun. 2019; 55: 11295
- 10 Zuo Z, Liu J, Nan J, Fan L, Sun W, Wang Y, Luan X. Angew. Chem. Int. Ed. 2015; 54: 15385
- 11 Li T, Xu F, Li X, Wang C, Wan B. Angew. Chem. Int. Ed. 2016; 55: 2861
- 12 Zhou M.-B, Song R.-J, Li J.-H. Angew. Chem. Int. Ed. 2014; 53: 4196
- 13a Yang Y, Zhou M.-B, Ouyang XH, Pi R, Song R.-J, Li J.-H. Angew. Chem. Int. Ed. 2015; 54: 6595
- 13b Zhang Z, Yang S, Li J, Liao X. J. Org. Chem. 2016; 81: 9639
- 14 Kahar N, Jadhav P, Reddy RV. R, Dawande S. Chem. Commun. 2020; 56: 1207
- 15 Li Y, Hu M, Li J.-H. ACS Catal. 2017; 7: 6757
- 16 Li Y, Li J.-H. Org. Lett. 2018; 20: 5323
- 17 Feng J.-J, Lin T.-Y, Zhu C.-Z, Wang H, Wu H.-H, Zhang J.-L. J. Am. Chem. Soc. 2016; 138: 2178
- 18 Guimond N, Fagnou K. J. Am. Chem. Soc. 2009; 131: 12050
- 19 Wang Y.-F, Toh KK, Lee J.-Y, Chiba S. Angew. Chem. Int. Ed. 2011; 50: 5927
- 20 Huang X.-C, Yang X.-H, Song R.-J, Li J.-H. J. Org. Chem. 2014; 79: 1025
- 21a Zhang X, Ouyang X.-H, Li Y, Chen B, Li J.-H. Adv. Synth. Catal. 2019; 361: 4955
- 21b Zhao Y, Shi C, Su X, Xia W. Chem. Commun. 2020; 56: 5259
- 22 Sun B, Yoshino T, Kanai M, Matsunaga S. Angew. Chem. Int. Ed. 2015; 54: 12968
- 23 Wang F, Wang Q, Bao M, Li X.-W. Chin. J. Catal. 2016; 37: 1423
- 24 Wang F, Qi Z, Sun J, Zhang X, Li X.-W. Org. Lett. 2013; 15: 6290
- 25 Morimoto K, Hirano K, Satoh T, Miura M. J. Org. Chem. 2011; 76: 9548
- 26 Nakanowatari S, Ackermann L. Chem. Eur. J. 2014; 20: 5409
- 27 Luo M.-J, Hu M, Song R.-J, He D.-L, Li J.-H. Chem. Commun. 2019; 55: 1124
- 28 Luo M.-J, Zhang T.-T, Cai F.-J, Li J.-H, He D.-L. Chem. Commun. 2019; 55: 7251
- 29 Ouyang X.-H, Hu C, Song R.-J, Li J.-H. Org. Lett. 2018; 20: 4659
- 30 Pi R, Zhou M.-B, Yang Y, Gao C, Song R.-J, Li J.-H. Chem. Commun. 2015; 51: 13550
- 31 Zhou M.-B, Pi R, Hu M, Yang Y, Song R.-J, Xia Y, Li J.-H. Angew. Chem. Int. Ed. 2014; 53: 11338
- 32 Li Y, Pi R, Ouyang X.-H, Song R.-J, Li J.-H. Org. Lett. 2019; 21: 397
- 33 Stuart DR, Bertrand-Laperle M, Burgess KM. N, Fagnou K. J. Am. Chem. Soc. 2008; 130: 16474
- 34 Liang Y.-J, Jiao N. Angew. Chem. Int. Ed. 2016; 55: 4035
- 35 Cui X, Xu X, Wojtas L, Kim MM, Zhang XP. J. Am. Chem. Soc. 2012; 134: 19981
- 36 Kuram MR, Bhanuchandra M, Sahoo AK. Angew. Chem. Int. Ed. 2013; 52: 4607
- 37 Liu J.-Q, Fang Z.-X, Zhang Q, Liu Q, Bi X.-H. Angew. Chem. Int. Ed. 2013; 52: 6953
For reviews, see:
For selected reviews, see: