Synthesis, Table of Contents Synthesis 2021; 53(12): 2051-2056DOI: 10.1055/s-0040-1706644 paper Palladium(II)-Catalyzed C(sp)–C(sp2) Coupling: A Direct Approach to Multi-Substituted Pyrrolo[1,2-a]pyrazines Chang He , Zijuan Wang , Yitong Chen , Guolin Zhang∗ , Yongping Yu∗ Recommend Article Abstract Buy Article All articles of this category Abstract A direct synthesis of multi-substituted pyrrolo[1,2-a]pyrazines via palladium(II)-catalyzed C(sp)–C(sp2) cascade coupling and intramolecular cyclization in the presence of ligand was developed. This reaction originates from phenylboronic acids and readily synthesized 2-carbonyl- or 2-formylpyrroloacetonitriles, and affords products in good to excellent yields for a diversity of substrates. Additionally, a possible mechanism for the transformation is proposed. Key words Key wordsC–C coupling - palladium - cascade reactions - substituted pyrrolo[1,2-a]pyrazines Full Text References References 1 Mokrov GV, Deeva OA, Gudasheva TA, Yarkov SA, Yarkova MA, Seredenin SB. Bioorg. Med. Chem. 2015; 23: 3368 2 Arban R, Bianchi F, Buson A, Cremonesi S, Di Fabio R, Gentile G, Micheli F, Pasquarello A, Pozzan A, Tarsi L, Terreni S, Tonelli F. Bioorg. Med. Chem. Lett. 2010; 20: 5044 3 Micheli F, Bertani B, Bozzoli A, Crippa L, Cavanni P, Di Fabio R, Donati D, Marzorati P, Merlo G, Paio A, Perugini L, Zarantonello P. Bioorg. Med. Chem. Lett. 2008; 18: 1804 4 Guillon J, Le Borgne M, Rimbault C, Moreau S, Savrimoutou S, Pinaud N, Baratin S, Marchivie M, Roche S, Bollacke A, Pecci A, Alvarez L, Desplat V, Jose J. Eur. J. Med. Chem. 2013; 65: 205 5 Hanasaki K, Ikeda M, Ono T. PCT Int. Appl WO 2002/000257, 2002 6 Hanasaki K, Ikeda M, Ono T. PCT Int. Appl WO 2002/000256, 2002 7 Hanasaki K, Ikeda M, Ono T. PCT Int. Appl WO 2002/000255, 2002 8 Garzan A, Willby MJ, Ngo HX, Gajadeera CS, Green KD, Holbrook SY, Hou C, Posey JE, Tsodikov OV, Garneau-Tsodikova S. ACS Infect. Dis. 2017; 3: 302 9 Kim J, Park M, Choi J, Singh DK, Kwon HJ, Kim SH, Kim I. Bioorg. Med. Chem. Lett. 2019; 29: 1350 10 Park S, Jung Y, Kim I. Tetrahedron 2014; 70: 7534 11 Nayak M, Pandey G, Batra S. Tetrahedron 2011; 67: 7563 12 Alfonsi M, Dell’Acqua M, Facoetti D, Arcadi A, Abbiati G, Rossi E. Eur. J. Org. Chem. 2009; 2852 13 Karmakar A, Ramalingam S, Basha M, Indasi GK, Belema M, Meanwell NA, Dhar TG. M, Rampulla R, Mathur A, Gupta A, Gupta AK. Synthesis 2019; 52: 441 14 Chen W, Hu M, Wu J, Zou H, Yu Y. Org. Lett. 2010; 12: 3863 15 Larock RC, Tian Q, Pletnev AA. J. Am. Chem. Soc. 1999; 121: 3238 16 Zhou C, Larock RC. J. Am. Chem. Soc. 2004; 126: 2302 17 Song H, Cheng N, She L.-Q, Wu Y, Liao W.-W. RSC Adv. 2019; 9: 29424 18 Xiong W, Chen Z, Shao Y, Li R, Hu K, Chen J. Org. Chem. Front. 2020; 7: 756 19 Yu H, Xiao L, Yang X, Shao L. Chem. Commun. 2017; 53: 9745 20 Qi L, Li R, Yao X, Zhen Q, Ye P, Shao Y, Chen J. J. Org. Chem. 2020; 85: 1097 21 Xiong W, Hu K, Lei Y, Zhen Q, Zhao Z, Shao Y, Li R, Zhang Y, Chen J. Org. Lett. 2020; 22: 1239 22 Yu Y, Zhang G, Wang Z, Chen W, Luo H, He C. Synthesis 2020; 52: 1659 23 Wang Z.-J, Chen W.-T, He C, Luo H.-F, Zhang G.-L, Yu Y.-P. Tetrahedron 2020; 76: 130953 24 Milen M, Ábrányi-Balogh P, Dancsó A, Simig G, Volk B. Tetrahedron 2014; 70: 465 25 Jeanmart S, Gagnepain J, Maity P, Lamberth C, Cederbaum F, Rajan R, Jacob O, Blum M, Bieri S. Bioorg. Med. Chem. 2018; 26: 2009 26 Hu S.-B, Chen Z.-P, Song B, Wang J, Zhou Y.-G. Adv. Synth. Catal. 2017; 359: 2762 Supplementary Material Supplementary Material Supporting Information
