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-00000084.xml
Synthesis 2017; 49(17): 3863-3873
DOI: 10.1055/s-0036-1590791
DOI: 10.1055/s-0036-1590791
feature
Diversified Synthesis of 2-(4-Oxo[1,2,3]triazolo[1,5-a]quinoxalin-5(4H)-yl)acetamide Derivatives through Ugi-4-CR and Copper-Catalyzed Tandem Reactions
The authors are grateful to National Natural Science Foundation of China (Grant 21572229) and Science and Technology Program of Guangzhou, China (Grant 201604016066) for their financial support.Further Information
Publication History
Received: 25 April 2017
Accepted after revision: 12 May 2017
Publication Date:
11 July 2017 (online)
![](https://www.thieme-connect.de/media/synthesis/201717/lookinside/thumbnails/ss-2017-e0272-fa_10-1055_s-0036-1590791-1.jpg)
§ These authors contributed equally.
Abstract
A diversified synthesis of 2-(4-oxo[1,2,3]triazolo-[1,5-a]quinoxalin-5(4H)-yl)acetamide derivatives is demonstrated. The protocol employs a Ugi four-component reaction for the assembling of N-(2-haloaryl)propynamide intermediates and followed by a copper-catalyzed tandem reaction of the synthetic N-(2-haloaryl)propynamides with sodium azide. Such a method provides rapid access to structurally varied and complex fused tricyclic scaffolds through readily available starting materials.
Key words
diversified synthesis - Ugi reaction - copper-catalyzed - tandem reaction - fused heterocyclesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590791.
- Supporting Information
-
References
- 1a Quin LD. Tyrell J. Fundamentals of Heterocyclic Chemistry: Importance in Nature and in the Synthesis of Pharmaceuticals. Wiley; Chichester: 2010
- 1b Joule JA. Mills K. Heterocyclic Chemistry . 5th ed. Wiley; Chichester: 2010
- 2 Witherup KM. Ransom RW. Graham AC. Bernard AM. Salvatore MJ. Lumma WC. Anderson PS. Pitzenberger SM. Varga SL. J. Am. Chem. Soc. 1995; 117: 6682
- 3a Mohr JT. Stoltz BM. Chem. Asian J. 2007; 2: 1476
- 3b Hong AY. Stoltz BM. Eur. J. Org. Chem. 2013; 2745
- 3c Yokoyama Y. Kondo K. Mitsuhashi M. Murakami Y. Tetrahedron Lett. 1996; 37: 9309
- 3d Yamada F. Makita Y. Somei M. Heterocycles 2007; 72: 599
- 4 Shen HC. Ding F.-X. Deng QL. Wilsie LC. Krsmanovic ML. Taggart AK. Carballo-Jane E. Ren N. Cai T.-Q. Wu T.-J. Wu KK. Cheng K. Chen Q. Wolff MS. Tong XC. Holt TG. Waters MG. Hammond ML. Tata JR. Colletti SL. J. Med. Chem. 2009; 52: 2587
- 5a Biagi G. Giorgi I. Livi O. Scartoni V. Betti L. Giannaccini G. Trincavelli ML. Eur. J. Med. Chem. 2002; 37: 565
- 5b Bertelli L. Biagi G. Giorgi I. Manera C. Livi O. Scarton V. Betti L. Giannaccini G. Trincavelli L. Barili PL. Eur. J. Med. Chem. 1998; 33: 113
- 6a Leach CA. Brown TH. Ife RJ. Keeling DJ. Laing SM. Parsons ME. Price CA. Wiggall KJ. J. Med. Chem. 1992; 35: 1845
- 6b Escolano C. Jones K. Tetrahedron Lett. 2000; 41: 8951
- 6c Brown TH. Ife RJ. Keeling DJ. Laing SM. Leach CA. Parsons ME. Price CA. Reavill DR. Wiggall KJ. J. Med. Chem. 1990; 33: 527
- 7 Suzuki F. Kuroda T. Nakasato Y. Manabe H. Ohmori K. Kitamura S. Ichikawa S. Ohno T. J. Med. Chem. 1992; 35: 4045
- 8 Schreiber SL. Burke MD. Angew. Chem. Int. Ed. 2004; 43: 46
- 9 Yan J. Zhou F. Qin D. Cai T. Ding K. Cai Q. Org. Lett. 2012; 14: 1262
- 10 For a recent review, see: Wei F. Wang W. Ma Y. Tung C.-H. Xu Z. Chem. Commun. 2016; 52: 14188
- 11a Wu Y.-M. Deng J. Li Y. Chen Q.-Y. Synthesis 2005; 1314
- 11b Li L. Zhang G. Zhu A. Zhang L. J. Org. Chem. 2008; 73: 3630
- 11c Zhang X. Hsung RP. Li H. Chem. Commun. 2007; 2420
- 11d Wei F. Li H. Song C. Ma Y. Zhou L. Tung C.-H. Xu Z. Org. Lett. 2015; 17: 2860
- 12a Selvaraju M. Sun C.-M. Adv. Synth. Catal. 2014; 356: 1329
- 12b Gomes AT. P. C. Martins PR. C. Rocha DR. Neves MG. P. M. S. Ferreira VF. Silva AM. S. Cavaleiro JA. S. da Silva F. deC. Synlett 2013; 41
- 12c Krishna PM. Ramachary DB. Peesapati S. RSC Adv. 2015; 5: 62062
- 12d Wang W. Peng X. Wei F. Tung C.-H. Xu Z. Angew. Chem. Int. Ed. 2016; 55: 649
- 12e Li L. Hao G. Zhu A. Fan X. Zhang G. Zhang L. Chem. Eur. J. 2013; 19: 14403
- 12f Alonso F. Moglie Y. Radivoy G. Yus M. Synlett 2012; 24: 2179
- 12g Yang D. Fu N. Liu Z. Li Y. Chen B. Synlett 2007; 278
- 12h Li L. Fan X. Zhang Y. Zhu A. Zhang G. Tetrahedron 2013; 69: 9939
- 12i Wang W. Wei F. Ma Y. Tung C.-H. Xu Z. Org. Lett. 2016; 18: 4158
- 13 Ugi I. Lohberger S. Karl R. Comprehensive Organic Synthesis; Part 2, Vol. 2. Trost BM. Fleming I. Pergamon Press; New York: 1991: 1083
- 14a Orru RV. A. de Greef M. Synthesis 2003; 1471
- 14b Hoesl CE. Nefzi A. Houghten RA. J. Comb. Chem. 2003; 5: 155
- 15 Zhou F. Liu J. Ding K. Liu J. Cai Q. J. Org. Chem. 2011; 76: 5346
For examples to trap organocuprates with electrophiles, see:
For examples of tandem CuAAC/oxidative coupling reactions, see: