Ethyl 3-amino-3-selenoxopropanoate as a new reagent for the synthesis of selenium-containing heterocycles

Abstract

Interaction of ethyl cyanoacetate with hydrogen selenide afforded new reagent for obtaining selenium-containing heterocycles such as ethyl 3-amino-3-selenoxopropanoate. Starting from the latter substituted selenazoles and ethyl 3-selenoxo-2,3,5,6,7,8-hexahydroisiquinoline-4-carboxylates were synthesized. The structure of the obtained compounds was confirmed by IR, NMR spectroscopy and gas chromatography-mass spectrometry.

New Derivatives of (Carbamoselenoyl)acetic Acid for the Synthesis of Functionally Substituted Selenazoles

“…1 H NMR spectrum, δ, ppm: 3.70 s (3H, CH 3 ), 3.98 s (2H, CH 2 ), 10.17 br.s and 10.62 br.s (1H each, NH 2 ). 13…”

“…1 The IR spectra were recorded in KBr on an IKS-40 spectrometer. The 1 H and 13 C NMR spectra were recorded on a Bruker spectrometer at 400 and 100 MHz, respectively, using DMSO-d 6 as solvent and tetramethylsilane as internal standard. The mass spectra (positive and negative ion detection) were run on an Orbitrap Elite high-resolution mass spectrometer (resolution 480000); a sample for HRMS analysis was dissolved in 1 mL of DMSO, the solution was diluted by a factor of 100 with 1% formic acid in acetonitrile, and the resulting solution was introduced into the electrospray ion source at a flow rate of 40 μL/min using a syringe pump; capillary voltage 3.5 kV, capillary temperature 275°C; source gas flows were turned off; internal calibration against [2DMSO + H] + (m/z 157.03515) for positive ions and dodecyl sulfate anion (m/z 265.14789) for negative ions.…”

“…A limited number of functionally substituted selenoamides are currently available. For example, only three derivatives of (carbamoselenoyl)acetic acid have been reported, namely ethyl and benzyl esters and amide [8][9][10][11][12][13]. In this communication we report the synthesis of previously unknown 3-amino-N-cyclopropyl-3selanylidenepropanamide (1a) and methyl 3-amino-3selanylidenepropanoate (1b) by reaction of 2-cyano-Ncyclopropylacetamide (2a) and methyl 2-cyanoacetate (2b), respectively, with hydrogen selenide.…”