REGIOSELECTIVE SYNTHESIS OF 1,3,5-TRISUBSTITUTED PYRAZOLES CONTAINING AN ANTHRANILIC ACID MOTIF

Authors

  • Виктор А. Савельев N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090
  • Анна А. Котова N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090 Novosibirsk State University, 1 Pirogova St., Novosibirsk 630090
  • Татьяна В. Рыбалова N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090 Novosibirsk State University, 1 Pirogova St., Novosibirsk 630090
  • Эльвира Э. Шульц N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090 Novosibirsk State University, 1 Pirogova St., Novosibirsk 630090

DOI:

https://doi.org/10.1007/5109

Keywords:

alkynyl ketones, ethynyl anthranilates, hydrazine, pyrazoles, cyclization, X-ray structural analysis

Abstract

An effective method was developed for the synthesis of 1,3,5-trisubstituted pyrazoles by using acetylenic ketones, obtained from ethyl 5-ethynylanthranilate, in reactions with substituted hydrazines and hydrazides. It was shown that the cyclization of ethyl 5-(3-aryl-3-oxopropinyl)anthranilates with arylhydrazines proceeded regioselectively and led to the formation of 1,3,5-trisubstituted pyrazoles containing an anthranilate moiety at the position С-3. Significant deterioration of regioselectivity was observed in the reactions of ethyl 5-(3-aryl-3-oxopropinyl)anthranilates with N-methyl- and N-tert-butylhydrazines. The initial products formed in reactions of ethyl 5-[3-(4-fluorophenyl)-3-oxopropinyl]anthranilate with benzoyl and isonicotinoyl hydrazides were 5-hydroxypyrazolines, which underwent dehydration in the presence of pyridine and thionyl chloride in benzene, giving the respective 1,3,5-trisubstituted pyrazoles.

Authors: Viktor A. Savel'ev, Anna A. Kotova, Tatyana V. Rybalova, Elvira E. Shults*

Author Biographies

Виктор А. Савельев, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090

Виктор Александрович Савельев

старший научный сотрудник

Анна А. Котова, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090 Novosibirsk State University, 1 Pirogova St., Novosibirsk 630090

Анна Алeксандровна Котова

Студентка дипломница НГУ

Татьяна В. Рыбалова, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090 Novosibirsk State University, 1 Pirogova St., Novosibirsk 630090

Татьяна Валерьевна Рыбалова

научный сотрудник центра спектральных исследований НИОХ СО РАН

Эльвира Э. Шульц, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090 Novosibirsk State University, 1 Pirogova St., Novosibirsk 630090

зав. Лабораторией медицинской химии

Downloads

Published

2019-09-26

Issue

Vol. 55 No. 10 (2019)

Section

Original Papers