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Synthesis 2019; 51(02): 516-521
DOI: 10.1055/s-0037-1609937
DOI: 10.1055/s-0037-1609937
paper
Na2CO3-Catalyzed N-Acylation of Indoles with Alkenyl Carboxylates
Authors
The work was supported by the Youth Science and Technology Talent Development Project in Education Department of Guizhou Province (Grant No. qianjiaohe KY zi [2017] number 261) and Innovation Team of Liupanshui Normal University (Grant No. LPSSYKJTD201601).
Weitere Informationen
Publikationsverlauf
Received: 07. Juni 2018
Accepted after revision: 04. August 2018
Publikationsdatum:
04. September 2018 (online)
Abstract
The N-acylation of indoles has been accomplished via inorganic base catalysis. It provided an efficient and simple catalysis system for the preparation of N-acylindoles with alkenyl carboxylates as acylating agents. A broad variety of indoles undergo the smooth N-acylation using Na2CO3 as catalyst in MeCN at 120 °C to give the corresponding N-acylindoles in good to excellent yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609937.
- Supporting Information (PDF)
-
References
- 1a Kochanowska-Karamyan AJ. Hamann MT. Chem. Rev. 2010; 110: 4489
- 1b Lancianesi S. Palmieri A. Petrini M. Chem. Rev. 2014; 114: 7108
- 2a Guchhait SK. Chaudhary V. Rana VA. Priyadarshani G. Kandekar S. Kashyap M. Org. Lett. 2016; 18: 1534
- 2b Kong L. Wang M. Zhang F. Xu M. Li Y. Org. Lett. 2016; 18: 6124
- 2c Zhou X.-Y. Chen X. Wang L.-G. Synlett 2016; 27: 2742
- 2d Yarlagadda S. Ramesh B. Reddy C. Srinivas RL. Sridhar B. Reddy BV. S. Org. Lett. 2017; 19: 170
- 2e Zhou X.-Y. Chen X. Wang L.-G. Synthesis 2017; 49: 3662
- 2f Zhou X.-Y. Chen X. Wang L.-G. Yang D. Li J.-H. Synlett 2018; 29: 835
- 3a Kuwano R. Sato K. Kurokawa T. Karube D. Ito Y. J. Am. Chem. Soc. 2000; 122: 7614
- 3b Wang D.-S. Chen Q.-A. Li W. Yu C.-B. Zhou Y.-G. Zhang X. J. Am. Chem. Soc. 2010; 132: 8909
- 3c Duan Y. Li L. Chen M.-W. Yu C.-B. Fan H.-J. Zhou Y.-G. J. Am. Chem. Soc. 2014; 136: 7688
- 4a Cacchi S. Fabrizi G. Chem. Rev. 2005; 105: 2873
- 4b Shiri M. Chem. Rev. 2012; 112: 3508
- 4c Boyarskiy VP. Ryabukhin DS. Bokach NA. Vasilyev AV. Chem. Rev. 2016; 116: 5894
- 5a Bur SK. Padwa A. Chem. Rev. 2004; 104: 2401
- 5b Mąkosza M. Wojciechowski K. Chem. Rev. 2004; 104: 2631
- 5c Busto E. Gotor-Fernández V. Gotor V. Chem. Rev. 2011; 111: 3998
- 5d Zhang H. Hu R.-B. Liu N. Li S.-X. Yang S.-D. Org. Lett. 2016; 18: 28
- 5e Morimoto N. Morioku K. Suzuki H. Takeuchi Y. Nishina Y. Org. Lett. 2016; 18: 2020
- 5f Petrone DA. Kondo M. Zeidan N. Lautens M. Chem. Eur. J. 2016; 22: 5684
- 6a Bras JL. Muzart J. Chem. Rev. 2011; 111: 1170
- 6b Liu C. Yuan J. Gao M. Tang S. Li W. Shi R. Lei A. Chem. Rev. 2015; 115: 12138
- 6c Yang Y. Lan J. You J. Chem. Rev. 2017; 117: 8787
- 7a Colby DA. Bergman RG. Ellman JA. Chem. Rev. 2010; 110: 624
- 7b Hummel JR. Boerth JA. Ellman JA. Chem. Rev. 2017; 117: 9163
- 8 Okauchi T. Itonaga M. Minami T. Owa T. Kitoh K. Yoshino H. Org. Lett. 2000; 2: 1485
- 9 Ottoni O. Neder AV. F. Dias AK. B. Cruz RP. A. Aquino LB. Org. Lett. 2001; 3: 1005
- 10 Taylor JE. Jones MD. Williams JM. J. Bull SD. Org. Lett. 2010; 12: 5740
- 11 Johansson H. Urruticoechea A. Larsen I. Pedersen DS. J. Org. Chem. 2015; 80: 471
- 12 Tang B.-X. Song R.-J. Wu C.-Y. Liu Y. Zhou M.-B. Wei W.-T. Deng G.-B. Yin D.-L. Li J.-H. J. Am. Chem. Soc. 2010; 132: 8900
- 13 Wu W. Su W. J. Am. Chem. Soc. 2011; 133: 11924
- 14 Akai S. Peat AJ. Buchwald SL. J. Am. Chem. Soc. 1998; 120: 9119
- 15 Jiang T.-S. Wang G.-W. Org. Lett. 2013; 15: 788
- 16 Ottoni O. Cruz R. Alves R. Tetrahedron 1998; 54: 13915
- 17 Heller ST. Schultz EE. Sarpong R. Angew. Chem. Int. Ed. 2012; 51: 8304
- 18 Umehara A. Ueda H. Tokuyama H. J. Org. Chem. 2016; 81: 11444
- 19 Ta L. Sundén H. Chem. Commun. 2018; 54: 531