Coupling of Anhydro-Aldose-Tosylhydrazones with N-Heterocycles

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Coupling of Anhydro-Aldose-Tosylhydrazones with N-Heterocycles

Marietta Tóth 1 , Ivett Cservenyák 1 , Tímea Kaszás 1 , Éva Juhász-Tóth 1 , Andrea E. Kulcsár 1 , Zsolt Szentjóbi 1 , Paola Granatino 1 , László Somsák 1

1 University of Debrecen, Debrecen, Hungary

In recent years, N-tosylhydrazones have been increasingly used in metal-free and transition metal-catalyzed coupling reactions instead of the unstable diazo compounds [1, 2]. Carbohydrate coupling reactions are poorly known, and couplings with sugar tosylhydrazones represent a completely new area of carbohydrate chemistry. Coupling reactions of N-tosylhydrazones can be applied for the formation of carbon-carbon and carbon-heteroatom bonds, as well. Examples of C-N couplings with amines and N-heterocycles can also be found in the literature [3, 4]. Under these preliminaries we started a systematic study about 4 years ago to investigate the applicability of anhydro-aldose-tosylhydrazones 1 [5] in coupling reactions. In this project C-O [6] and C-S [7] bonds were successfully formed under metal-free conditions and C-C bonds [8, 9] in Pd-catalyzed reactions. As a next step we started to investigate the possibility of C-N bond formation by coupling of 1 with amines and N-heterocycles. Reactions of 1 with amines were not successful, but the metal-free reactions with N-heterocycles provided the N-(β-D-glycopyranosyl)methyl-heterocycles 2 (See Figure 1). In this presentation we disclose our results.

Figure 1.

The research was supported by the EU and co-financed by the European Regional Development Fund under the project GINOP-2.3.2-15-2016-00008, and by the National Research, Development and Innovation Office under the project FK128766.

Qiu, D.; Mo, F. Y.; Zhang, Y.; Wang, J. B. Recent advances in transition-metal-catalyzed cross-coupling reactions with N-tosylhydrazones. In Advances in Organometallic Chemistry, Perez, P. J., Ed., 2017, Vol. 67, pp 151-219.

Xia, Y.; Qiu, D.; Wang, J. B. Chem. Rev. 2017, 117, 13810-13889.

Hamze, A.; Tréguier, B.; Brion, J.-D.; Alami, M. Org. Biomol. Chem. 2011, 9, 6200-6204.

Zeng, X.; Cheng, G.; Shen, J.; Cui, X. Org. Lett. 2013, 15, 322-3025.

Tóth, M.; Kövér, K. E.; Bényei, A.; Somsák, L. Org. Biomol. Chem. 2003, 1, 4039-4046.

Kaszás, T.; Tóth, M.; Kun, S.; Somsák, L. RSC Adv. 2017, 7, 10454-10462.

Kaszás, T.; Tóth, M.; Somsák, L. New J. Chem. 2017, 41, 13871-13880.

Kaszás, T.; Ivanov, A.; Tóth, M.; Ehlers, P.; Langer, P.; Somsák, L. Carbohydr. Res. 2018, 466, 30-38.

Kaszás, T.; Tóth, M.; Langer, P.; Somsák, L. Adv. Synth. Catal. 2019, 361, 105–117

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