Reaction of 2-chloro-5-methylbenzoquinone with Β-aminocrotonic ester derivatives

The reaction of 2-chloro-5-methylbenzoquinone with -aminocrotonic ester derivatives was studied by PMR spectroscopy in CD₃COOD. The spectra indicate the formation of intermediate hydroquinone and quinone derivatives, which subsequently transform into the corresponding indoles. It was shown that the indolization proceeds unequivocally at the 3-position of the initial benzoquinone, and the rate of formation of the indole derivatives decreases with increase in the size of the substituent at the nitrogen atom of the -aminocrotonic ester. The starting, intermediate compounds and the end products observed in the PMR spectra were identified by comparison with specially synthesized compounds.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 324–328, March, 1990.     

Reaction of 2,3-epoxypropyl alkyl sulfides with carboxylic acids and phenol

Russian Chemical Bulletin -     

Mass-spectrometric study of the cyclization of diazo ketones. 2. Cyclization of 1-diazo-4-sulfonylaminobutan-2-ones to N-sulfonylpyrrolidin-3-ones

A comparison of the mass spectra of 1-diazo-4-sulfonylamino-butan-2-ones and N-sulfonylpyrrolidin-3-ones makes it possible to conclude that under the conditions of electron impact and chemical ionization the molecular ions of the investigated diazo ketones lose a molecule of nitrogen and undergo partial cyclization to the corresponding pyrrolidinones without undergoing the Wolff rearrangement.See [1] for Communication 1.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 919–925, July, 1982.