DIGITAL TRANSFORMATION: MODERN TECHNOLOGIES FOR PEOPLE AND EDUCATION

Engineering notes

It is known that many heterocyclic compounds, even relatively simple ones, are difficult to obtain, significantly limiting their scope of application.Therefore, the search for new regioselective heterocyclizations based on readily available reagents is highly relevant.Various amidoalkylating agents, in particular those obtained from Schiff bases according to the general scheme, are among such promising reagents: CHEMISTRY DIGITAL TRANSFORMATION: MODERN TECHNOLOGIES FOR PEOPLE AND EDUCATION 20Below is the diagram according to which the synthesis was carried out:General synthesis procedure.1) N-ethylidene anion (1).Mix equimolar amounts of acetaldehyde and aniline in toluene.Boil with a Dean-Stark trap until the calculated amount of water is absorbed.2) N-phenyl-N-1-chloroethene acetamide (2).Add an equimolar amount of chloroacetate to the residue and leave at room temperature for 24 hours.3) N-(1-N-acetaminophenethene)adamantylglycine methanoate (3).Add equimolar amounts of 1-adamantylglycine methyl ester, prepared by the standard method by dropping SOCl2 into a methanol solution of 1-adamantylglycine, and triethylamine.Boil for 3 hours.Filter off the precipitated triethylamine hydrochloride.The solvent is removed in vacuo.Yield 96% (methanol).4) 1- 3]diazepin-5(2H)-one (4).A minimum amount of concentrated hydrochloric acid is added to a solution of product (3) in methanol and the mixture is left at room temperature overnight.The solution is made alkaline with a methanolic solution of NaOH.The solvent is removed in vacuo.Dry benzene is added and the mixture is again evaporated to a small volume.SOCl2 is added with a molar excess of 10%.The mixture is left at room temperature overnight.The solvent and excess SOCl2 are removed in vacuo.Dry toluene and an equimolar amount of Et3N are added.The mixture is refluxed for 8 hours.The solvent is removed in vacuo.The residue is crystallized from ethanol.Yield 93%.The structure of compound (4), ( 5) was confirmed based on 1 H and 13 C NMR, IR and mass spectra.

Chinese explanation / 中文解读

中文解读待补充：本站会优先为端到端自动驾驶、BEV感知、3D目标检测、轨迹预测、路径规划、LiDAR感知等高价值论文补充中文说明。

Original abstract

It is known that many heterocyclic compounds, even relatively simple ones, are difficult to obtain, significantly limiting their scope of application.Therefore, the search for new regioselective heterocyclizations based on readily available reagents is highly relevant.Various amidoalkylating agents, in particular those obtained from Schiff bases according to the general scheme, are among such promising reagents: CHEMISTRY DIGITAL TRANSFORMATION: MODERN TECHNOLOGIES FOR PEOPLE AND EDUCATION 20Below is the diagram according to which the synthesis was carried out:General synthesis procedure.1) N-ethylidene anion (1).Mix equimolar amounts of acetaldehyde and aniline in toluene.Boil with a Dean-Stark trap until the calculated amount of water is absorbed.2) N-phenyl-N-1-chloroethene acetamide (2).Add an equimolar amount of chloroacetate to the residue and leave at room temperature for 24 hours.3) N-(1-N-acetaminophenethene)adamantylglycine methanoate (3).Add equimolar amounts of 1-adamantylglycine methyl ester, prepared by the standard method by dropping SOCl2 into a methanol solution of 1-adamantylglycine, and triethylamine.Boil for 3 hours.Filter off the precipitated triethylamine hydrochloride.The solvent is removed in vacuo.Yield 96% (methanol).4) 1- 3]diazepin-5(2H)-one (4).A minimum amount of concentrated hydrochloric acid is added to a solution of product (3) in methanol and the mixture is left at room temperature overnight.The solution is made alkaline with a methanolic solution of NaOH.The solvent is removed in vacuo.Dry benzene is added and the mixture is again evaporated to a small volume.SOCl2 is added with a molar excess of 10%.The mixture is left at room temperature overnight.The solvent and excess SOCl2 are removed in vacuo.Dry toluene and an equimolar amount of Et3N are added.The mixture is refluxed for 8 hours.The solvent is removed in vacuo.The residue is crystallized from ethanol.Yield 93%.The structure of compound (4), ( 5) was confirmed based on 1 H and 13 C NMR, IR and mass spectra.

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