Synthesis and neurotropic activity of the derivatives of fused triazolo[4,3-c]- and triazolo[1,5-c]pyrimidines

N- and / or O- Alkylation of Quinazolinone Derivatives

“…The urgent need was the repetition of these [30][31] studies, which contradicts the results of work [35], where instead of the O-alkylation product, the N-alkylation product was obtained in the course of reactions under almost the same conditions, which we proved using various methods of NMR spectroscopy of compounds obtained by the above methods. The alkylation of 6,7-dimethoxyquinazolin-4(3H)one with ethyl chloroacetate under the above [30][31][35][36][37][38] conditions also led to the formation of the N-alkylation product 3b (R 1 =OCH 3 , R 2 =CH 2 CO 2 CH 2 CH 3 ) with 82 % yield (pathway A), which was confirmed by 2D NMR spectroscopy. The formation of the N-alkylation product is confirmed by the correlation of the protons of the NCH 2 group with the 2-H proton of the quinazolinone in the COSY spectrum, as well as the chemical shift of the carbon of the NCH 2 group equal to 47.79ppm (Figure 3).…”

“…The above is very important for us when conducting our SAR in the search for effective HDAC/VEGFR-2 bi-inhibitors, since the authors of work [29,35] performed SAR to search for VEGFR-2 inhibitors on supposedly 4-O-alkylquinazolines, whereas in reality they had products of N-alkylation (Scheme 4). This led us to develop an alternative route [37,38] for the synthesis of 4-alkyloxyquinazolines.…”

One‐pot effective synthesis of new heterocyclic system: Pyrano[4′,3′:4,5]pyrido[2,3‐d]pyrimidin‐6‐one

“…Previously two methods of synthesis for the preparation of derivatives of aryl-substituted 8-thioxo-pyrano [3,4-c] pyridine were presented [10][11][12]. In this study the new more efficient one-pot method for obtaining the compounds 3a-d have been developed.…”

“…Recently, we have carried out the synthesis of compounds containing the pyrano, pyridine, and pyrimidine moieties [10][11][12]. This work has been devoted to the synthesis of 6-amino-3,3-dimethyl-7-arylsubstituted-8-thioxo(oxo)pyrano [3,4-c]pyridines and new heterosystem-pyrano [4 0 ,3 0 :4,5]pyrido [2,3-d]pyrimidin-6-one.…”

Synthesis, neurotropic activity and SAR of new S-alkyl derivatives of 8- pyrazol-1-yl pyrano[3,4-c]pyridines

“…[5][6][7] The current study is a continuation of our research on the synthesis and evaluation of neurotropic activity of fused tri-and tetracyclic systems containing pyridine ring. [8][9][10][11] Development of new derivatives of 8-pyrazol-1yl--6-thioalkyl-3,4,6,7-tetrahydro-1H-pyrano [3,4-c]pyridine are described here, in which we synthesized 8-(3,5dimethyl-1H-pyrazol-1-yl)-3,3-dimethyl-6-oxo-3,4,6,7-tetrahydro-1H-pyrano [3,4-c]pyridine-5-carbonitriles through a Smiles rearrangement. The neurotropic properties and SAR of the synthesized compounds were also studied.…”