THE SYNTHESIS OF 2<i>H</i>-PYRIDO[3,4-<i>c</i>][1,2]BENZOXAZINE-2,4(3<i>H</i>)-DIONES FROM 6-OXO-6<i>H</i>-1,2-OXAZINE-3-CARBOXYLATES

Authors

  • Дмитрий С. Иванов Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997
  • Эльвира Р. Зайцева Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997
  • Александр Ю. Смирнов Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997 Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997
  • Алексей В. Низовцев Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997
  • Надежда С. Балеева Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997 Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997
  • Михаил С. Баранов Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997 Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997

DOI:

https://doi.org/10.1007/7070

Keywords:

imides, nitroacetic esters, oxazinones, condensation

Abstract

A simple procedure was developed for the synthesis of 2H-pyrido[3,4-c][1,2]benzoxazine-2,4(3H)-diones by the treatment of ofluorophenyl-substituted 6-oxo-6H-1,2-oxazine-3-carboxylates with primary amines. The reaction proceeded according to the mechanism previously described for the formation of 3-(hydroxyimino)pyridine-2,6-diones followed by intramolecular nucleophilic substitution involving the hydroxyimino group to form the 1,2-oxazine ring.

Authors: Dmitry S. Ivanov, Elvira R. Zaitseva, Alexander Yu. Smirnov*, Alexey V. Nizovtsev, Nadezhda S. Baleeva, Mikhail S. Baranov

Author Biographies

Дмитрий С. Иванов, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997

Группа химии гетероциклических соединений

Эльвира Р. Зайцева, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997

Группа химии гетероциклических соединений

Александр Ю. Смирнов, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997 Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997

Группа химии гетероциклических соединений

Алексей В. Низовцев, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997

Группа химии гетероциклических соединений

Надежда С. Балеева, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997 Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997

Группа химии гетероциклических соединений

Михаил С. Баранов, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997 Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997

Группа химии гетероциклических соединений

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Published

2023-02-21

Issue

Vol. 59 No. 1/2 (2023)

Section

Short Communications