A. A. Zubenko, L. N. Divaeva, A. S. Morkovnik, V. S. Sochnev, O. P. Demidov, V. V. Chekrysheva, A. I. Klimenko, A. E. Svyatogorova, “β-Carbolines as intermediates in indirect heteroarylation of tryptamines exemplified by the synthesis of 2-pyrazolyltryptamines”, Mendeleev Commun., 2023, Volume 33, Issue 5,Pages <nobr>645

This article is cited in 1 paper

Communications

β-Carbolines as intermediates in indirect heteroarylation of tryptamines exemplified by the synthesis of 2-pyrazolyltryptamines

A. A. Zubenko^a, L. N. Divaeva^b, A. S. Morkovnik^b, V. S. Sochnev^b, O. P. Demidov^c, V. V. Chekrysheva^a, A. I. Klimenko^a, A. E. Svyatogorova^a

^a North-Caucasian Zonal Research Veterinary Institute, Novocherkassk, Russian Federation
^b Institute of Physical and Organic Chemistry, Southern Federal University, Rostov-on-Don, Russian Federation
^c North-Caucasus Federal University, Stavropol, Russian Federation

Abstract: A cyclization–recyclization pathway for indirect 2-heteroarylation of tryptamines has been suggested by the example of introducing the pyrazolyl moiety. The process involves the intermediate cyclization of tryptamines into push–pull type β-carboline semi-products. The relative stability of the tautomeric forms of 2-pyrazolyltryptamines has been estimated using the DFT method.

Keywords: tryptamines, 1-aroylmethylidene-1,2, 3, 4-tetrahydro-β-carbolines, β-carbolines, recyclization, 2-(pyrazol-3-yl)tryptamine, 2-(pyrazol-3-yl)-O-methylserotonins, pyrazolylmelatonins, quantum chemical calculations.

Language: English

DOI: 10.1016/j.mencom.2023.09.018

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