The Mannich reaction in the synthesis of N,S-containing heterocycles. 7. Effective one-pot synthesis of derivatives of spiro[3,5,7,11-tetraazatricyclo-[7.3.1.02,7]tridec-2-ene-13,4′-piperidine]

Abstract

Functionally substituted derivatives of pyridine-2-(1H)-thione, and their tautomers 2-mercaptopyridines, and also their partially hydrogenated analogs have been enduring compounds in the arsenal of fine chemical synthesis for the last twenty years as promising reactive synthons [2-4], opening broad vistas for the preparation of a series of condensed heterocyclic systems [5][6][7]. Nevertheless there is only solary reports in the literature on the problem of aminomethylation of 2-mercaptopyridines [8]. It follows from multitudinous data in the literature that aminomethylation of 2-mercaptoazoles and -azines is a general method for the preparation of condensed derivatives of 1,3,5-thiadazines. In particular, derivatives of sym-triazolo [3,4-b] [1,3,5]thiadiazine [9-16], thiazolo[3',4':1,5][1,2,4]triazolo[3,4-b][1,3,5]thiadiazine [17], imidazo[2,1-b][1,3,5]thiadiazine [18, 19], 1,2,4-triazino[3,2-b][1,3,5]thiadiazine [19], and 1,3,5-thiadiazino[3,2-a]benzimidazole [20] have been obtained by "double" Mannich condensations. We have shown previously with a series of 2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates that, depending on the structure of the substrate, aminomethylation can lead to the formation of _______ * For Communication 6, see [1].

Synthesis of derivatives of 3,5,7,11-tetraaza-tricyclo[7.3.1.02,7]tridec-2-ene-8-selenone

“…The 1 H NMR spectra of selenones 3 are in good accord with the data for related 8-trioxo-3,5,7,11-tetraazatricyclo[7.3.1.0 2,7 ]tridec-2-enes [3][4][5][6][7], whose structure was demonstrated unequivocally by X-ray diffraction crystallographic analysis [5][6][7].…”

Probing chemical space of tick‐borne encephalitis virus reproduction inhibitors with organoselenium compounds

“…Such scaffolds were never studied previously in any biological assays. To date, the only known approach to the construction of the tricyclic core of 11 ‐like 3,5,7,11‐tetraazatricyclo[7.3.1.0 2,7 ]tridec‐2‐enes is based on the one‐step protocol including the treatment of C(3),C(5),N(1),C(6)NH 2 polynucleophilic 6‐amino‐1,4‐dihydro‐ or 6‐amino‐1,2,3,4‐tetrahydropyridine substrates with primary amines and an excess of HCHO. Despite the complexity of the tricyclic structure, the synthetic procedure is simple and efficient, giving rise to 3,5,7,11‐tetraazatricyclo[7.3.1.0 2,7 ]tridec‐2‐enes in good yields.…”