Intramolecular Arylation of 2-Nitrobenzenesulfonamides: A Route to Diverse Nitrogenous Heterocycles
- 507 Downloads
In addition to being an integral component of numerous drugs, 2- and 4-nitrobenzenesulfonyl (Nos) groups are used as protecting/activating agents for the selective alkylation of primary amines. 2-Nos amides are also useful intermediates for the synthesis of fused nitrogenous heterocycles. This chapter focuses on the use of 2-Nos amides as intramolecular arylation agents and on the application of C- and N-aryl derivatives for the synthesis of diverse heterocycles in the solid phase.
KeywordsArylation Heterocycles Nitrobenzenesulfonamides Solid-phase synthesis
This research was supported by the Department of Chemistry and Biochemistry, University of Notre Dame, by National program of Sustainability (LO1304), and research grant 16-06446S from the Czech Science Foundation (GACR).
- 11.Lupi V, Penso M, Foschi F, Gassa F, Mihali V, Tagliabue A (2009) Highly stereoselective intramolecular α-arylation of self-stabilized non-racemic enolates: synthesis of α-quaternary α-amino acid derivatives. Chem Commun (33):5012–5014Google Scholar
- 21.Bonanomi M, Palazzo G (1977) Products of the reaction between 1H-indazol-3-ol and ethyl chloroacetate. Farmaco Sci 32(7):490–501Google Scholar
- 35.Schutznerova E, Verdia P, Krchnak V (2016) Fused ring molecular scaffold with 3D architecture for constrained peptidomimetics: polymer-supported stereoselective synthesis of tetrahydrobenzo[e]pyrazino[2,1-c][1,2,4]thiadiazinone 6,6-dioxide via N-acyl Iminiums. ACS Comb Sci 18(10):655–659CrossRefGoogle Scholar