Tin(II)chloride catalyzed synthesis of pyranoquinolines, phenanthridinone and phenanthridine derivatives

Diastereoselective Synthesis of Novel and Enantiopure Tetrahydropyrano[3,2-c]quinolines

“…Tetrahydropyrano [3,2-c]quinoline scaffolds are synthetically important targets due to their substantial presence in both natural and synthetic products with interesting agrochemical, catalytic, and therapeutic properties, such as psychotropic, antiallergic, anti-inflammatory, and estrogenic activity. [1][2][3][4][5] As a result, various methodologies have been reported for their synthesis as well as their derivatives; [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] of which, the Povarov reaction 21 which involves the reaction of an aromatic imine (in a two component reaction) or aniline (in a three component reaction) with benzaldehyde and electron-rich alkenes such as dihydropyran (DHP) in the presence of an acid catalyst/promotor has been the mainstay. In the three-component reaction, the reaction is proposed to proceed first via condensation of aniline 1 with benzaldehyde 2 to yield imine 3.…”

SnCl 2 -catalyzed multicomponent coupling: synthesis of 1,3-oxazolidine derivatives using paraformaldehyde as a C1 feedstock

“…16 Over the years tin( ii ) chloride, a cost-effective Lewis acid catalyst, has found applications in diverse organic synthesis. 36–42 Apart from this, the orbital structure of tin compounds facilitates their complex formation with various transition metals, leading to highly active catalysts. 43–49…”

“…16 Over the years tin(II) chloride, a costeffective Lewis acid catalyst, has found applications in diverse organic synthesis. [36][37][38][39][40][41][42] Apart from this, the orbital structure of tin compounds facilitates their complex formation with various transition metals, leading to highly active catalysts. [43][44][45][46][47][48][49] Herein, we report an additive-free transformation of aniline, epoxide, and paraformaldehyde into 1,3-oxazolidine derivatives using SnCl 2 as the catalyst (Scheme 4).…”

Diastereoselective Synthesis of Pyranoquinolines on Zirconium‐Containing UiO‐66 Metal‐Organic Frameworks

“…Various homogeneous and heterogeneous acid catalysts, including SnCl 2 , SbCl 3 doped on hydroxyapatite (SbCl 3 ‐HPA), tungstophosphoric acid supported on nanosized MCM‐41 (TPA/MCM‐41), perchloric acid adsorbed on silica gel (HClO 4 ‐SiO 2 ), GdCl 3 , and ferric sulfate, have been reported for the synthesis of tetrahydropyranoquinolines. However, some of the methods used so far suffer from limitations such as the use of large amounts of catalyst (up to 50 mol‐%), very low diastereoselectivities, or poor catalyst reusability.…”