EventsThe 20th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-20-a003
This submission belongs to the session a. General Organic Synthesis of the event The 20th International Electronic Conference on Synthetic Organic Chemistry
Published date
01 Nov, 2016
Citation
Amparo Luna, Benito Alcaide, Pedro Almendros, Alejandro Escobar, Fernando Herrera, Gold-catalyzed cyclization of Baylis–Hillman adducts derived from formyl-indoles, in Proceedings of The 20th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2016, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-20-a003
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Gold-catalyzed cyclization of Baylis–Hillman adducts derived from formyl-indoles

Benito Alcaide 1
image
Pedro Almendros 2
Alejandro Escobar 1
Fernando Herrera 1
Amparo Luna 3
1. Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid, Spain;
2. Instituto de Química Orgánica General, Consejo Superior de Investigaciones Científicas, IQOG-CSIC, Juan de la Cierva 3, 28006 Madrid, Spain
3. Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid, Spain;, Seychelles
Abstract

Indoles are important structural motifs found in biological and pharmacological compounds.[1] Therefore, the construction and functionalization of indole skeletons has attracted considerable attention. On the other hand, the use of gold salts has gained a lot of attention in the recent times because of their powerful soft Lewis acidic nature. Such a property allows gold catalysts to activate unsaturated functionalities such as alkynes, alkenes, and allenes, to create C–C bonds under extremely mild conditions.[2] Moreover, Baylis–Hillman (BH) adducts are usually flexible and multifunctional products which can be easily transformed in a huge number of derivatives.[3] However, although many efforts have been made in these fields, the gold-catalyzed reactions using BH adducts derived from formyl-indoles as substrates constitute an unexplored field of noble metal catalysis. In our continuing efforts on the construction of potentially bioactive heterocycles,[4] we wish to report now details of the gold-catalyzed direct synthesis of dihydrocyclopenta[b]indoles from indole-tethered a-hydroxacrylates (Baylis–Hillman adducts) derived from formyl-indoles. The newly formed five-membered ring arises from a selective indole hydroarylation followed by dehydration.

[1] (a) Kaushik,N. K.;Kaushik, N.; Attri, P.; Kumar, N.; Kim, C. H.; Verma, A. K.; Choi, E. H. Molecules 2013, 18, 6620. (b) Vicente, R. Org. Biomol. Chem. 2011, 9, 6469.

[2] (a) Hashmi, A. S. K. Acc. Chem. Res. 2014, 47, 864; (b) Obradors, C.; Echavarren, A. M. Acc. Chem. Res. 2014, 47, 902; (c) Alcaide, B.; Almendros, P. Acc.Chem. Res. 2014, 47, 939.

[3] (a) Wei, Y.; Shi, M. Chem. Rev. 2013, 113, 6659; (b) Liu, T.-Y.; Xiec, M.; Chen, Y.-C. Chem. Soc. Rev. 2012, 41, 4101; (c) Singh, V.; Batra. S. Tetrahedron 2008, 64, 4511.

[4] (a) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Fernández, I.; Gómez-Campillos, G. Chem. Eur. J. 2016, 22, 285; (b) Alcaide, B.; Almendros, P.; Fernández, I.; Martín-Montero, R.; Martínez-Peña, F.; Ruiz, M. P.; Torres, M. R. ACS Catal. 2015, 5, 4842. (c) Alcaide, B.; Almendros, P.; Alonso J.-M.; Fernández, I.; Chemm. Commun. 2012, 48, 6604.

Keywords
Baylis–Hillman
indoles
gold catalysis
Manuscript
ECSOC-2016-AmparoLuna.pdf
Poster
presentation-AmparoLuna.pdf
presentation-AmparoLuna.pdf
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