Synthesis of Chromenoimidazoles, Annulated with an Azaindole Moiety, through a Base-Promoted Domino Reaction of Cyano­methyl Quaternary Salts

Leonid G. Voskressensky; Olga A. Storozhenko; Alexey A. Festa; Roman A. Novikov; Alexey V. Varlamov

doi:10.1055/s-0036-1589496

Synthesis, Table of Contents

CC BY 4.0 · Synthesis 2017; 49(12): 2753-2760
DOI: 10.1055/s-0036-1589496

paper

Copyright with the author

Synthesis of Chromenoimidazoles, Annulated with an Azaindole Moiety, through a Base-Promoted Domino Reaction of Cyanomethyl Quaternary Salts

Leonid G. Voskressensky*

^aPeoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya St. 6, 117198 Moscow, Russian Federation Email: lvoskressensky@sci.pfu.edu.ru

,

Olga A. Storozhenko

^aPeoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya St. 6, 117198 Moscow, Russian Federation Email: lvoskressensky@sci.pfu.edu.ru

,

Alexey A. Festa

^aPeoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya St. 6, 117198 Moscow, Russian Federation Email: lvoskressensky@sci.pfu.edu.ru

,

Roman A. Novikov

^bEngelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilova 32, 119334 Moscow, Russian Federation

,

Alexey V. Varlamov

^aPeoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya St. 6, 117198 Moscow, Russian Federation Email: lvoskressensky@sci.pfu.edu.ru

› Author Affiliations

Abstract

All articles of this category

Abstract

The reactivity of N-cyanomethyl quaternary salts of 4-, 5- and 7-azaindoles towards salicylic aldehydes has been studied. The interaction of azaindolium salts with salicylic aldehydes proceeds as a base-promoted domino reaction, giving the corresponding chromenoimidazopyrrolopyridines. In the case of the 7-(cyanomethyl)-7-azaindolium salt, the reaction was found to be more sensitive, but the use of the 1-methyl-substituted salt allowed the synthesis of the desired compounds, incorporating the heterocyclic core of isogranulatimide C, a marine natural product.

Key words

azaindoles - domino reaction - isogranulatimides - iminium salts - chromenoimidazoles - microwave

Full Text

References

References
1 Chezal J.-M, Paeshuyse J, Gaumet V, Canitrot D, Maisonial A, Lartigue C, Gueiffier A, Moreau E, Teulade J.-C, Chavignon O, Neyts J. Eur. J. Med. Chem. 2010; 45: 2044-2044
2 Hranjec M, Pavlovi G, Marjanovi M, Kralj M, Karminski-Zamola G. Eur. J. Med. Chem. 2010; 45: 2405-2405
3 Moraes EC, Meirelles GV, Honorato RV, de Souza TA. C. B, de Souza EE, Murakami MT, de Oliveira PS. L, Kobarg J. Molecules 2015; 20: 1176-1176

4a Jiang X, Zhao B, Britton R, Lim LY, Leong D, Sanghera JS, Zhou B.-B, Piers E, Andersen RJ, Roberge M. Mol. Cancer Ther. 2004; 3: 1221-1221
4b Roberge M, Berlinck RG. S, Xu L, Anderson HJ, Lim LY, Curman D, Stringer CM, Friend SH, Davies P, Vincent I, Haggarty SJ, Kelly MT, Britton R, Piers E, Andersen RJ. Cancer Res. 1998; 58: 5701-5701
4c Hènon H, Conchon E, Hugon B, Messaoudi S, Golsteyn RM, Prudhomme M. Anti-Cancer Agents Med. Chem. 2008; 8: 577-577

5 Lavrard H, Salvetti B, Mathieu V, Rodriguez F, Kiss R, Delfourne E. ChemMedChem 2015; 10: 607-607
6 Hugon B, Anizon F, Bailly C, Golsteyn RM, Pierré A, Léonce S, Hickman J, Pfeiffer B, Prudhomme M. Bioorg. Med. Chem. 2007; 15: 5965-5965
7 Lima CF, Costa M, Proenca MF, Pereira-Wilson C. Eur. J. Pharm. Sci. 2015; 72: 34-34

8a Piers E, Britton R, Andersen RJ. J. Org. Chem. 2000; 65: 530-530
8b Sanchez-Martinez C, Shih C, Faul MM, Zhu G, Paal M, Somoza C, Li T, Kumrich CA, Winneroski LL, Xun Z, Brooks HB, Patel BK. R, Schultz RM, DeHahn TB, Spencer CD, Watkins SA, Considine E, Dempsey JA, Ogg CA, Campbell RM, Anderson BA, Wagner J. Bioorg. Med. Chem. Lett. 2003; 13: 3835-3835
8c Delfourne E. Tetrahedron Lett. 2011; 52: 6560-6560
8d Salvetti B, Lavrard H, Delfourne E. Tetrahedron Lett. 2014; 55: 6560-6560

For our studies on the construction of fused chromenoimidazoles, see:

9a Voskressensky LG, Festa AA, Sokolova EA, Varlamov AV. Tetrahedron 2012; 68: 5498-5498
9b Voskressensky LG, Festa AA, Sokolova EA, Khrustalev VN, Varlamov AV. Eur. J. Org. Chem. 2012; 6124-6124
9c Voskressensky LG, Sokolova EA, Festa AA, Khrustalev VN, Van Tuyen N, Anh LT, Varlamov AV. Chem. Heterocycl. Compd. 2013; 49: 484-484
9d Voskressensky LG, Sokolova EA, Festa AA, Varlamov AV. Tetrahedron Lett. 2013; 54: 5172-5172

10 Voskressensky LG, Storozhenko OA, Festa AA, Khrustalev VN, Dang TT. A, Nguyen VT, Varlamov AV. Tetrahedron Lett. 2015; 56: 6475-6475
11 Mahadevan I, Rasmussen M. Tetrahedron 1993; 49: 1331-1331

Supplementary Material

Supporting Information

Synthesis of Chromenoimidazoles, Annulated with an Azaindole Moiety, through a Base-Promoted Domino Reaction of Cyano­methyl Quaternary Salts

Synthesis of Chromenoimidazoles, Annulated with an Azaindole Moiety, through a Base-Promoted Domino Reaction of Cyanomethyl Quaternary Salts