RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2021; 53(12): 2051-2056
DOI: 10.1055/s-0040-1706644
DOI: 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
This project was supported from the National Key R & D Program of China (No. 2017YFE0102200), National Natural Science Foundation of China (No. 81673291), and Diabetes National Research Group, USA to Y. Yu.
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706644.
- Supporting Information
Publikationsverlauf
Eingereicht: 28. September 2020
Angenommen nach Revision: 03. Dezember 2020
Artikel online veröffentlicht:
26. Januar 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
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