Synthesis 2020; 52(11): 1659-1665
DOI: 10.1055/s-0039-1691731
paper
© Georg Thieme Verlag Stuttgart · New York

Cascade Reactions to Substituted 1H-Pyrrole-3-carbonitriles via Ligand-Free Palladium(II)-Catalyzed C(sp)–C(sp2) Coupling

Zijuan Wang
,
Wenteng Chen
,
Haofan Luo
,
Chang He
,
Guolin Zhang
,
Yongping Yu
Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Science, Zhejiang University, Hangzhou 310058, P. R. of China   Email: guolinzhang@zju.edu.cn   Email: yyu@zju.edu.cn
› Author Affiliations
This study was supported by the National Natural Science Foundation of China (No. 81602959 to J.S.), Natural Science Foundation of Zhejiang Province (LY18H300001), and Multiple Sclerosis National Research Institute, USA (to W.C.).
Further Information

Publication History

Received: 26 November 2019

Accepted after revision: 08 January 2020

Publication Date:
25 February 2020 (online)


Abstract

An efficient and simple synthesis of substituted 1H-pyrrole-3-carbonitriles was developed. This reaction is a palladium(II)-catalyzed cascade of C(sp)–C(sp2) coupling followed by intramolecular C–N bond formation. The method can tolerate various substrates with satisfactory yields. Its ligand-free conditions and high efficiency make this method particularly attractive.

Supporting Information

 
  • References

  • 1 Minetto G, Raveglia LF, Sega A, Taddei M. Eur. J. Org. Chem. 2005; 5277
  • 2 Chen F, Shen T, Cui Y, Jiao N. Org. Lett. 2012; 14: 4926
  • 3 Ran L, Ren Z, Wang Y, Guan Z. Green Chem. 2014; 16: 112
  • 4 Wang M, Xu H, Liu T, Feng Q, Yu S, Wang S, Li Z. Eur. J. Med. Chem. 2011; 46: 1463
  • 5 Tafi A, Costi R, Botta M, Di Santo R, Corelli F, Massa S, Ciacci A, Manetti F, Artico M. J. Med. Chem. 2002; 45: 2720
  • 6 Maeda H, Mihashi Y, Haketa Y. Org. Lett. 2008; 10: 3179
  • 7 Wu X, Li K, Wang S, Liu C, Lei A. Org. Lett. 2016; 18: 56
  • 8 Munde M, Lee M, Neidle S, Arafa R, Boykin DW, Liu Y, Bailly C, Wilson WD. J. Am. Chem. Soc. 2007; 129: 5688
  • 9 Portevin B, Tordjman C, Pastoureau P, Bonnet J, De Nanteuil G. J. Med. Chem. 2000; 43: 4582
  • 10 Lehuédé J, Fauconneau B, Barrier L, Ourakow M, Piriou A, Vierfond J. Eur. J. Med. Chem. 1999; 34: 991
  • 11 Jiang S, Lu H, Liu S, Zhao Q, He Y, Debnath AK. Antimicrob. Agents Chemother. 2004; 48: 4349
  • 12 Raghavendra K, Barik TK, Sharma P, Bhatt RM, Srivastava HC. Malaria J. 2011; 10: 10
  • 13 Vermeulen T, Schoonbeek H, De Waard MA. Pest Manag. Sci. 2001; 57: 393
  • 14 Shinozaki S, Nomoto H, Kondo Y, Sakamoto H, Hayashi Y, Yamamoto H, Lefor AK, Osawa H. Kaohsiung J. Med. Sci. 2016; 32: 255
  • 15 Scott DR, Munson KB, Marcus EA, Lambrecht NW. G, Sachs G. Aliment. Pharmacol. Therap. 2015; 42: 1315
  • 16 Hantzsch A. Eur. J. Inorg. Chem. 2010; 1474
  • 17 Milgram BC, Eskildsen K, Richter SM, Scheidt WR, Scheidt KA. J. Org. Chem 2007; 72: 3941
  • 18 Mothana B, Boyd RJ. J. Mol. Struct.: THEOCHEM 2007; 811: 97
  • 19 Moiseeva IV, Lukin PM, Nasakin OE, Romanov VN, Tafeenko VA, Bulai AKh, Sharbatyan P. Chem. Heterocycl. Comp. 1992; 28: 232
  • 20 Foley LH. Tetrahedron Lett. 1994; 35: 5989
  • 21 Ikemoto T. (Takeda Pharmaceutical) WO 2010098351, 2010
  • 22 Chen J, Li C, Zhou Y, Sun C, Sun T. ChemCatChem 2019; 11: 1943
  • 23 Menichincheri M, Albanese C, Alli C, Ballinari D, Bargiotti A, Caldarelli M, Ciavolella A, Cirla A, Colombo M, Colotta F, Croci V, D’Alessio R, D’Anello M, Ermoli A, Fiorentini F, Forte B, Galvani A, Giordano P, Isacchi A, Martina K, Molinari A, Moll JK, Montagnoli A, Orsini P, Orzi F, Pesenti E, Pillan A, Roletto F, Scolaro A, Tatò M, Tibolla M, Valsasina B, Varasi M, Vianello P, Volpi D, Santocanale C, Vanotti E. J. Med. Chem. 2010; 53: 7296
  • 24 Yu H, Xiao L, Yang X, Shao L. Chem. Commun. 2017; 53: 9745