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-00000083.xml
Synlett 2019; 30(09): 1026-1036
DOI: 10.1055/s-0037-1611476
DOI: 10.1055/s-0037-1611476
account
Recent Developments in the Synthesis of Nitrogen-Containing Heterocycles through C–H/N–H Bond Functionalizations and Oxidative Cyclization
We gratefully acknowledge the invaluable contributions from talented students and colleagues in our laboratories, and financial support from the National Natural Science Foundation of China (Grants Nos. 21805166, 21801053, and 21403256), the 111 Project of Hubei Province (Grant No. 2018-19-1), The Youth Innovation Promotion Association CAS (2018456), China Three Gorges University, Hainan University, Shenzhen University, Lanzhou University, and the Chinese Academy of Sciences.
Further Information
Publication History
Received: 02 December 2018
Accepted after revision: 23 January 2019
Publication Date:
22 February 2019 (online)
Dedicated to Professor Dong-Sheng Li on the occasion of his 50th birthday.
Abstract
The synthesis and structure of nitrogen-containing heterocycles are fascinating because these compounds have a great richness of structural, physicochemical, and biological properties. Therefore, the development of improved ways for the synthesis of polyfunctional nitrogen-containing heterocycles continues to be a challenging goal. This account describes developments in the discovery of C–H/N–H bond functionalization and oxidative cyclization procedures for the synthesis of nitrogen-containing heterocycles (aziridines, indoles, indolizines, triazoles, imidazoles, oxazoles, thiazoles, quinoxalines, triazines, and pyridines) in our laboratories during the last 15 years.
1 Introduction
2 Synthesis of Aziridines
3 Synthesis of Indoles and Indolizines
4 Synthesis of Triazoles
5 Synthesis of Imidazoles
6 Synthesis of Oxazoles and Thiazoles
7 Synthesis of Quinoxalines, Triazines, and Pyridines
8 Conclusion and Outlook
-
References
- 1a Wang L, Guan Z.-R, Ding M.-W. Org. Biomol. Chem. 2016; 14: 2413
- 1b Liu Y.-W, Xie Y.-B, Li D.-J, Wang L. Russ. J. Gen. Chem. 2015; 85: 2163
- 1c Liu X, Astruc D. Adv. Synth. Catal. 2018; 360: 3426
- 1d Wang L, Xie Y.-B, Huang NY, Yan J, Hu W.-M, Liu M.-G. ACS Catal. 2016; 6: 4010
- 1e Xie Y.-B, Ye S.-P, Chen W.-F, Hu Y.-L, Li D.-J, Wang L. Asian J. Org. Chem. 2017; 6: 746
- 1f Yan J, Yang Y, Ishida M, Mori S, Zhang B, Feng Y, Furuta H. Chem. Eur. J. 2017; 23: 11375
- 1g Zhang N, Chen J, Cheng K, Li Y, Wang L, Zheng K, Yang Q, Li D, Yan J. Res. Chem. Intermed. 2017; 43: 2921
- 1h Li Y, Yan J, Cheng K, Kong S, Zheng K, Wang L, Zhang N. Res. Chem. Intermed. 2017; 43: 5337
- 1i Li Y, Yan J, Xiao S, Zhang B, Lu F, Cheng K, Li D, Feng Y, Zhang N. Tetrahedron Lett. 2016; 57: 3226
- 1j Yan J, Zhou Y, Zhang N, Chen H, He X, Xiao S, Zheng K. Res. Chem. Intermed. 2017; 43: 5395
- 1k Wang L, Sun M, Ding M.-W. Eur. J. Org. Chem. 2017; 2568
- 2a Dhakshinamoorthy A, Garcia H. Chem. Soc. Rev. 2014; 43: 5750
- 2b Dastan A, Kulkarnia A, Török B. Green Chem. 2012; 14: 17
- 2c Zhou Y, Wang Y, Xiao S, He X, Zhang N, Li D, Zheng K. J. Fluoresc. 2017; 27: 799
- 2d Baran PS, Guerrero CA, Ambhaikar NB, Hafensteiner BD. Angew. Chem. Int. Ed. 2005; 44: 606
- 2e Zhang T, Li Y, Yan J, Liang Y, Xu B, Zheng K, Zhang N. Tetrahedron 2018; 74: 2807
- 2f Zhou Y, Zeng F, Liu Y, Li M, Xiao S, Yan J, Zheng N, Zheng K. Tetrahedron Lett. 2018; 59: 3253
- 2g Zheng K, Chen H, Fang S, Wang Y. Sens. Actuators, B 2016; 233: 193
- 2h Zhou Y, He X, Cheng H, Wang Y, Xiao S, Zhang N, Li D, Zheng K. Sens. Actuators, B 2017; 247: 626
- 2i Zhou Y, Yan J, Zhang N, Li D, Xiao S, Zheng K. Sens. Actuators, B 2018; 258: 156
- 2j Zhang Y, Yang H, Guan S, Liu Z, Guo L, Xie J, Zhang J, Zhang N, Song J, Zhang B, Feng Y. Dyes Pigm. 2018; 157: 64
- 3a Köhling P, Schmidt AM, Eilbracht P. Org. Lett. 2003; 5: 3213
- 3b Caron S, Vazquez E. J. Org. Chem. 2003; 68: 4104
- 3c Jiang B, Yang C.-G, Wang J. J. Org. Chem. 2002; 67: 1396
- 3d Liu X, Manzur C, Novoa N, Celedón S, Carrillo D, Hamon J.-R. Coord. Chem. Rev. 2018; 357: 144
- 3e Bringmann G, Tasler S, Endress H, Mühlbacher J. Chem. Commun. 2001; 761
- 4 Katritzky AR, Pozharskii AF. Handbook of Heterocyclic Chemistry . Pergamon; Oxford: 2000. 2nd ed.
- 5 Clark RD, Repke DB. Heterocycles 1984; 22: 195
- 6 Johnson PD, Aristoff PA. J. Org. Chem. 1990; 55: 1374
- 7 Hughes DL. Org. Prep. Proced. Int. 1993; 25: 607
- 8 Wacker DA, Kasireddy P. Tetrahedron Lett. 2002; 43: 5189
- 9 Xiang L, Zhang F, Chen B, Pang X, Yang X, Huang G, Yan R. RSC Adv. 2015; 5: 29424
- 10 Guo X, Han J, Liu Y, Qin M, Zhang X, Chen B. J. Org. Chem. 2017; 82: 11505
- 11 Zhang X, Wang P, Han J, Guo X, Chen B. ChemistrySelect 2018; 3: 3014
- 12 Tang M.-C, Zou Y, Watanabe K, Walsh CT, Tang Y. Chem. Rev. 2017; 117: 5226
- 13 Judd TC, Williams RM. Angew. Chem. Int. Ed. 2002; 41: 4683
- 14 Watson ID, Yu L, Yudin A. Acc. Chem. Res. 2006; 39: 194
- 15 Meng X, Chen W, Zhang Y, Chen Y, Chen B. J. Heterocycl. Chem. 2014; 51: 937
- 16 Phun LH, Aponte-Guzman J, France S. Angew. Chem. Int. Ed. 2012; 51: 3198 ; corrigendum: Angew. Chem. Int. Ed. 2013, 52, 5669
- 17 Xiang L, Yang Y, Zhou X, Liu X, Li X, Kang X, Yan R, Huang G. J. Org. Chem. 2014; 79: 10641
- 18a Tian L, Sun Y, Li H, Zheng X, Cheng Y, Liu X, Qian B. J. Inorg. Biochem. 2005; 99: 1646
- 18b Buckle DR, Rockell CJ. M, Smith H, Spicer BA. J. Med. Chem. 1986; 29: 2262
- 18c Alvarez R, Velázquez S, San-Felix A, Aquaro S, De Clercq E, Perno C.-F, Karlsson A, Balzarini J, Camarasa MJ. J. Med. Chem. 1994; 37: 4185
- 18d Al-Masoudi NA, Al-Soud YA. Tetrahedron Lett. 2002; 43: 4021
- 18e Wang CL, Ikhlef D, Kahlal S, Saillard J.-Y, Astruc D. Coord. Chem. Rev. 2016; 316: 1
- 18f Liu X, Astruc D. Coord. Chem. Rev. 2018; 359: 112
- 18g Liang LY, Astruc D. Coord. Chem. Rev. 2011; 255: 2933
- 19a Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
- 19b Zhang L, Chen X, Xue P, Sun HH. Y, Williams ID, Sharpless KB, Fokin VV, Jia G. J. Am. Chem. Soc. 2005; 127: 15998
- 20 Yang D, Fu N, Liu Z, Li Y, Chen B. Synlett 2007; 278
- 21 Wang D, Li N, Zhao M, Shi W, Ma C, Chen B. Green Chem. 2010; 12: 2120
- 22 Wang D, Zhao M, Liu X, Chen Y, Li N, Chen B. Org. Biomol. Chem. 2012; 10: 229
- 23 Meng X, Xu X, Gao T, Chen B. Eur. J. Org. Chem. 2010; 5409
- 24 Wang D, Chen S, Chen B. Tetrahedron Lett. 2014; 55: 7026
- 25 Wang D, Chen S, Wang J, Astruc D, Chen B. Tetrahedron 2016; 72: 6375
- 26 Li N, Wang D, Li J, Shi W, Li C, Chen B. Tetrahedron Lett. 2011; 52: 980
- 27 Li J, Wang D, Zhang Y, Li J, Chen B. Org. Lett. 2009; 11: 3024
- 28 Li J, Zhang Y, Wang D, Wang W, Gao T, Wang L, Li J, Huang G, Chen B. Synlett 2010; 1617
- 29 Liu X, Li J, Chen B. New J. Chem. 2013; 37: 965
- 30 Zhang Y, Li X, Li J, Chen J, Meng X, Zhao M, Chen B. Org. Lett. 2012; 14: 26
- 31 Liu X, Li X, Chen Y, Wang D, Chen J, Chen B. Asian J. Org. Chem. 2013; 2: 212
- 32 Zhang L, Tang D, Gao J, Wang J, Wu P, Meng X, Chen B. Synthesis 2016; 48: 3924
- 33 Sarges R, Howard HR, Browne RG, Lebel LA, Seymour AP, Koe BK. J. Med. Chem. 1990; 33: 2240
- 34 Samai S, Nandi GC, Singh P, Singh MS. Tetrahedron 2009; 65: 10155
- 35a Balalaie S, Arabanian A. Green Chem. 2000; 2: 274
- 35b Kidwai M, Mothsra P, Bansal V, Somvanshi RK, Ethayathulla AS, Dey S, Singh TP. J. Mol. Catal. A: Chem. 2007; 265: 177
- 35c Kantevari S, Vuppalapati SV. N, Biradar DO, Nagarapu L. J. Mol. Catal. A: Chem. 2007; 266: 109
- 35d Heravi MM, Derikvand F, Bamoharram FF. J. Mol. Catal. A: Chem. 2007; 263: 112
- 35e Nagarapu L, Apuri S, Kantevari S. J. Mol. Catal. A: Chem. 2007; 266: 104
- 36 Liu X, Wang D, Chen Y, Tang D, Chen B. Adv. Synth. Catal. 2013; 355: 2798
- 37 Tang D, Wu P, Liu X, Chen Y.-X, Guo S.-B, Chen W.-L, Li J.-G, Chen B.-H. J. Org. Chem. 2013; 78: 2746
- 38 Liu X, Wang D, Chen B. Tetrahedron 2013; 69: 9417
- 39 Qu J, Wu P, Tang D, Meng X, Chen Y, Guo S, Chen B. New J. Chem. 2015; 39: 4235
- 40 Li Y, Fu Y, Ren C, Tang D, Wu P, Meng X, Chen B. Org. Chem. Front. 2015; 2: 1632
- 41 Wu P, Qu J, Li Y, Guo X, Tang D, Meng X, Yan R, Chen B. Adv. Synth. Catal. 2015; 357: 3868
- 42 Wu P, Zhang L, Zhang X, Guo X, Chen B. Chin. J. Chem. 2016; 34: 363
- 43 Zhang X, Wu P, Fu Y, Zhang F, Chen B. Tetrahedron Lett. 2017; 58: 870
- 44 Yuan H, Chen Y, Song J, Chen C, Chen B. Chin. J. Chem. 2013; 31: 1247
- 45 Tang D, Guo X, Wang Y, Wang J, Li J, Huang Q, Chen B. Tetrahedron Lett. 2015; 56: 5982
- 46 Chen J, Qu J, Zhang Y, Chen Y, Liu N, Chen B. Tetrahedron 2013; 69: 316
- 47 Meng X, Zhang J, Chen B, Jing Z, Zhao P. Catal. Sci. Technol. 2016; 6: 890
- 48 Qin M, Tian Y, Guo X, Yuan X, Yang X, Chen B. Asian J. Org. Chem. 2018; 7: 1591
- 49 Viirre RD, Evindar G, Batey RA. J. Org. Chem. 2008; 73: 3452
- 50 Hein DW, Alheim RJ, Leavitt JJ. J. Am. Chem. Soc. 1957; 79: 427
- 51 Wang Y, Meng X, Yang Y, Zhang L, Guo S, Tang D, Li Y, Chen B. Chem. Commun. 2015; 51: 1905
- 52 Fang T, Tan Q, Ding Z, Liu B, Xu B. Org. Lett. 2014; 16: 2342
- 53 Larksarp C, Alper H. J. Org. Chem. 2000; 65: 2773
- 54 Meng X, Wang Y, Wang Y, Chen B, Jing Z, Chen G, Zhao P. J. Org. Chem. 2017; 82: 6922
- 55 Meng X, Wang Y, Chen B, Chen G, Jing Z, Zhao P. Org. Process Res. Dev. 2017; 21: 2018
- 56 Zhang F, Wang J, Zhang X, Meng X, Chen B. ChemistrySelect 2017; 2: 8717
- 57 Yang X, Guo X, Qin M, Yuan X, Jing H, Chen B. Org. Biomol. Chem. 2018; 16: 3104
- 58 Yuan X, Liu Y, Qin M, Yang X, Chen B. ChemistrySelect 2018; 3: 5541
- 59 Meng X, Bi X, Yu C, Chen G, Chen B, Jing Z, Zhao P. Green Chem. 2018; 20: 4638
- 60 Dailey S, Feast JW, Peace RJ, Sage IC, Till S, Wood EL. J. Mater. Chem. 2001; 11: 2238
- 61 Xiao Q, Xia Y, Li H, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2011; 50: 1114
- 62 Song J, Li X, Chen Y, Zhao M, Dou Y, Chen B. Synlett 2012; 23: 2416
- 63 Chen Y, Li K, Zhao M, Li Y, Chen B. Tetrahedron Lett. 2013; 54: 1627
- 64 Yuan H, Li K, Chen Y, Wang Y, Cui J, Chen B. Synlett 2013; 24: 2315
- 65 Meng X, Bi X, Wang Y, Chen G, Chen B, Jing Z, Zhao P. Catal. Commun. 2017; 89: 34
- 66 Liu Y, Guo X, Tang D, Wang J, Wu P, Han J, Chen B. Chin. J. Chem. 2017; 35: 1222
- 67 Fu Y, Wang P, Guo X, Wu P, Meng X, Chen B. J. Org. Chem. 2016; 81: 11671
- 68 Guo X, Yang X, Qin M, Liu Y, Yang Y, Chen B. Asian J. Org. Chem. 2018; 7: 692
- 69 Han J, Guo X, Liu Y, Fu Y, Yan R, Chen B. Adv. Synth. Catal. 2017; 359: 2676
- 70a Chen W, Yan R, Tang D, Guo S, Meng X, Chen B. Tetrahedron 2012; 68: 7956
- 70b Gao T, Zhao M, Meng X, Li C, Chen B. Synlett 2011; 1281
- 70c Liu X, Chen Y, Li K, Wang D, Chen B. Chin. J. Chem. 2012; 30: 2285
- 70d Liu X, Yu G, Li J, Wang D, Chen Y, Shi K, Chen B. Synlett 2013; 24: 1588
- 70e Wang P, Fu Y, Guo X, Chen B. Asian J. Org. Chem. 2017; 6: 1398
- 70f Chen Y, Guo S, Li K, Qu J, Yuan H, Hua Q, Chen B. Adv. Synth. Catal. 2013; 355: 711
- 70g Guo S, Li Y, Wang Y, Guo X, Meng X, Chen B. Adv. Synth. Catal. 2015; 357: 950