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): 4035-4044
DOI: 10.1055/s-0036-1589042
DOI: 10.1055/s-0036-1589042
paper
Synthesis of N-Sulfonyl Ynamido-Phosphonates: Valuable Partners for Cycloadditions
Further Information
Publication History
Received: 24 March 2017
Accepted after revision: 03 May 2017
Publication Date:
20 June 2017 (online)
Abstract
N-Sulfonyl ynamido-phosphonates were prepared from sulfonamides and bromo alkynylphosphonates through a direct copper-catalyzed coupling reaction. The substrates were obtained in good to excellent yields. The latter are valuable partners to react with nitrile-oxides to form isoxazoles in good yields and with an exclusive regioselectivity.
Supporting Information
- Supporting information for this article is available online at https://doi.org /10.1055/s-0036-1589042.
- Supporting Information
-
References
- 1 DeKorver KA. Li H. Lohse AG. Hayashi R. Lu Z. Zhang Y. Hsung RP. Chem. Rev. 2010; 110: 5064
- 2 Evano G. Coste A. Jouvin K. Angew. Chem. Int. Ed. 2010; 49: 2840
- 3 Evano G. Jouvin K. Coste A. Synthesis 2013; 17
- 4 Zhang Y. Hsung RP. Tracey MR. Kurtz KC. M. Vera EL. Org. Lett. 2004; 6: 1151
- 5 Hamada T. Ye X. Stahl SS. J. Am. Chem. Soc. 2008; 130: 833
- 6 Coste A. Karthikeyan G. Couty F. Evano G. Angew. Chem. Int. Ed. 2009; 48: 4381
- 7 Jouvin K. Couty F. Evano G. Org. Lett. 2010; 12: 3272
- 8 Yang Y. Zhang X. Liang Y. Tetrahedron Lett. 2012; 53: 6557
- 9 Jouvin K. Coste A. Bayle A. Legrand F. Karthikeyan G. Tadiparthi K. Evano G. Organometallics 2012; 31: 7933
- 10 Jouvin K. Heimburger J. Evano G. Chem. Sci. 2012; 3: 756
- 11 Jin X. Yamaguchi K. Mizuno N. Chem. Commun. 2012; 4974
- 12 DeKorver KA. Walton MC. North TD. Hsung RP. Org. Lett. 2011; 13: 4862
- 13 Priebbenow DL. Becker P. Bolm C. Org. Lett. 2013; 15: 6155
- 14 Wang L. Huang H. Priebbenow DL. Pan F.-F. Bolm C. Angew. Chem. Int. Ed. 2013; 52: 3478
- 15 Sueda T. Oshima A. Teno N. Org. Lett. 2011; 13: 3996
- 16 Theunissen C. Lecomte M. Jouvin K. Laouiti A. Guissart C. Heimburger J. Loire E. Evano G. Synthesis 2014; 46: 1157
- 17 Marzo L. Parra A. Frías M. Alemán J. García Ruano JL. Eur. J. Org. Chem. 2013; 4405
- 18 Frei R. Waser J. J. Am. Chem. Soc. 2013; 135: 9620
- 19 Rodríguez D. Martínez-Esperón M. Castedo L. Saá C. Synlett 2007; 1963
- 20 Gillie AD. Jannapu Reddy R. Davies PW. Adv. Synth. Catal. 2016; 358: 226
- 21 Svintsitskaya NI. Aleksandrova AV. Dogadina AV. Ionin BI. Russ. J. Gen. Chem. 2007; 77: 963
- 22 Svintsitskaya NI. Aleksandrova AV. Dogadina AV. Ionin BI. Russ. J. Gen. Chem. 2008; 78: 157
- 23 Svintsitskaya NI. Aimakov OA. Dogadina AV. Ionin BI. Russ. J. Gen. Chem. 2009; 79: 1461
- 24 Perez V. Rabasso N. Fadel A. Eur. J. Org. Chem. 2016; 320
- 25 Fadel A. Legrand F. Evano G. Rabasso N. Adv. Synth. Catal. 2011; 353: 263
- 26 Gomes F. Fadel A. Rabasso N. J. Org. Chem. 2012; 77: 5439
- 27 Adler P. Gomes F. Fadel A. Rabasso N. Eur. J. Org. Chem. 2013; 7546
- 28 Adler P. Fadel A. Rabasso N. Tetrahedron 2014; 70: 4437
- 29 Adler P. Fadel A. Rabasso N. Chem. Commun. 2015; 3612
- 30 Adler P. Fadel A. Prunet J. Rabasso N. Org. Biomol. Chem. 2017; 15: 387
- 31 Kankala S. Kankala RK. Gundepaka P. Thota N. Nerella S. Gangula MR. Guguloth H. Kagga M. Vadde R. Vasam CS. Bioorg. Med. Chem. Lett. 2013; 23: 1306
- 32 Peifer C. Abadleh M. Bischof J. Hauser D. Schattel V. Hirner H. Knippschild U. Laufer S. J. Med. Chem. 2009; 52: 7618
- 33 Simoni D. Rondanin R. Baruchello R. Rizzi M. Grisolia G. Eleopra M. Grimaudo S. Cristina AD. Pipitone MR. Bongiorno MR. Aricò M. Invidiata FP. Tolomeo M. J. Med. Chem. 2008; 51: 4796
- 34 Zhang X. Zhang Y. Huang J. Hsung RP. Kurtz KC. M. Oppenheimer J. Petersen ME. Sagamanova IK. Shen L. Tracey MR. J. Org. Chem. 2006; 71: 4170
- 35 Gao Y. Wang G. Chen L. Xu P. Zhao Y. Zhou Y. Han L.-B. J. Am. Chem. Soc. 2009; 131: 7956
- 36 Qu Z. Chen X. Yuan J. Qu L. Li X. Wang F. Ding X. Zhao Y. Can. J. Chem. 2012; 90: 747
- 37 Aguiar AM. Chattha MS. J. Org. Chem. 1971; 36: 2719
- 38 Nishikawa T. Shibuya S. Hosokawa S. Isobe M. Synlett 1994; 485
- 39 Ahmadibeni Y. Dash C. Le Grice SF. J. Parang K. Tetrahedron Lett. 2010; 51: 3010
- 40 Hsung RP. Li H. You L. Zhang X. Johnson WL. Figueroa R. Heterocycles 2007; 74: 553
- 41 Grecian S. Fokin VV. Angew. Chem. Int. Ed. 2008; 47: 8285
- 42 Shen Y. Zheng J. Xin Y. Lin Y. Qi M. J. Chem. Soc., Perkin Trans. 1 1995; 997
- 43 Oakdale JS. Sit RK. Fokin VV. Chem. Eur. J. 2014; 20: 11101
- 44 Brel V. Synthesis 2009; 3405
- 45 Volkova YA. Averina EB. Grishin YK. Bruheim P. Kuznetsova TS. Zefirov NS. J. Org. Chem. 2010; 75: 3047
- 46 Vereshchagina YA. Alimova AZ. Sharova EV. Artyushin OI. Chachkov DV. Ishmaeva EA. Russ. J. Org. Chem. 2013; 49: 1369
- 47 Feuer H. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis: Novel Strategies in Synthesis. John Wiley & Sons; Weinheim: 2008
- 48 Chen CC. Waser J. Chem. Commun. 2014; 12923