Tandem Approach to Functionalized Pyrrolo[3,4-a]carbazole-1,3-diones via a Pd-catalyzed Indole-to-carbazole Transformation

Lianghua Guo , Mei Xu , Yong Jian , Sheng Liu , Weidong Pan , Lian Duan

Chemical Research in Chinese Universities ›› 2019, Vol. 35 ›› Issue (4) : 621 -626.

PDF
Chemical Research in Chinese Universities ›› 2019, Vol. 35 ›› Issue (4) : 621 -626. DOI: 10.1007/s40242-019-8399-8
Article

Tandem Approach to Functionalized Pyrrolo[3,4-a]carbazole-1,3-diones via a Pd-catalyzed Indole-to-carbazole Transformation

Author information +
History +
PDF

Abstract

A one-pot and efficient three-component reaction of indoles, acrylates and maleimides for the synthesis of pyrrolo[3,4-a]carbazole-1,3-dione derivatives was developed. Theree C-C bonds and one ring were created in a single step via an indole-to-carbazole transformation triggered by Pd(II)-catalyzed direct C3-alkenylation of indoles.

Keywords

Carbazole / One-pot / Tandem reaction / Three-component reaction / Indole-to-carbazole

Cite this article

Download citation ▾
Lianghua Guo, Mei Xu, Yong Jian, Sheng Liu, Weidong Pan, Lian Duan. Tandem Approach to Functionalized Pyrrolo[3,4-a]carbazole-1,3-diones via a Pd-catalyzed Indole-to-carbazole Transformation. Chemical Research in Chinese Universities, 2019, 35(4): 621-626 DOI:10.1007/s40242-019-8399-8

登录浏览全文

4963

注册一个新账户 忘记密码

References

[1]

Schmidt A W, Reddy K R, Knölker H J. Chem. Rev., 2012, 112: 3193.

[2]

Tsutsumi L S, Gündisch D, Sun D Q. Curr. Top. in Med. Chem., 2016, 16: 1290.

[3]

Gluszynska A. Eur. J. Med. Chem., 2015, 94: 405.

[4]

Joseph B, Facompré M, Costa H D, Routier S, Mérour J Y, Colson P, Houssier C, Bailly C. Bioorg. Med. Chem., 2001, 9: 1533.

[5]

Conchon E, Anizon F, Golsteyn R M, Léonce S, Pfeiffer B, Prudhomme M. Tetrahedron, 2006, 62: 11136.

[6]

Conchon E, Anizon F, Aboab B, Golsteyn R M, Léonce S, Pfeiffer B, Prudhomme M. Eur. J. Med. Chem., 2008, 43: 282.

[7]

Ty N, Dupeyre G, Chabot G G, Seguin J, Quentin L, Chiaroni A, Tillequin F, Scherman D, Michel S, Cachet X. Eur. J. Med. Chem., 2010, 45: 3726.

[8]

Pfeuffer L, Pindur U. Helvetica Chimica Acta, 1987, 70: 1419.

[9]

Pindur U, Kim N H, Eitel M. Tetrahedron Lett., 1990, 31: 1551.

[10]

Pindur U, Christian O. Tetrahedron, 1992, 48: 3515.

[11]

Noland W E, Walhstrom M J, Konkel M J, Brigham M E, Trowbridge A G, Konkel L M C, Gourneau R P, Scholten C A, Lee N H, Condoluci J J, Gac T S, Pour M M, Radford P M. J. Heterocyclic. Chem., 1992, 30: 81.

[12]

Biswas Soumen, Dagar Anuradha, Srivastava Anvita, Samanta Sampak. Access to Substituted Carbazoles in Water by a One-Pot Sequential Reaction of α,β-Substituted Nitro Olefins with 2-(3-Formyl-1H-indol-2-yl)acetates. European Journal of Organic Chemistry, 2015, 2015(20): 4493 4503

[13]

Neo A G, Bornadiego A, Diaz J, Marcaccini S, Marcos C F. Org. Biomol. Chem., 2013, 11: 6546.

[14]

Grimster N P, Gauntlett C, Godfrey C R A, Gaunt M J. Angew. Chem. Int. Ed., 2005, 44: 3125.

[15]

Chen W L, Gao Y R, Mao S, Zhang Y L, Wang Y F, Wang Y Q. Org. Lett., 2012, 14: 5920.

[16]

Ozaki K, Zhang H, Ito H, Lei A, Itami K. Chem. Sci., 2013, 4: 3416.

[17]

Verma A K, Danodia A K, Saunthwa R K, Patel M, Choudhary D. Org. Lett., 2015, 17: 3658.

[18]

Laha J K, Dayal N. Org. Lett., 2015, 17: 4742.

[19]

Lin K, Jian Y, Zhao P, Zhao C S, Pan W D, Liu S. Org. Chem. Front., 2018, 5: 590.

[20]

An Y L, Yang Z H, Zhang H H, Zhao S Y. Org. Lett., 2016, 18: 152.

AI Summary AI Mindmap
PDF

124

Accesses

0

Citation

Detail

Sections
Recommended

AI思维导图

/