СИНТЕЗ 2H-[1,2]ОКСАЗИНО[3,4-c]ХИНОЛИН-2,5(6H)-ДИОНОВ ИЗ 6-ОКСО-6H-1,2-ОКСАЗИН-3-КАРБОКСИЛАТОВ

Эльвира Р. Зайцева; Дмитрий С. Иванов; Александр Ю. Смирнов; Надежда С. Балеева; Михаил С. Баранов

doi:10.1007/7348

Authors

Эльвира Р. Зайцева Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia
Дмитрий С. Иванов Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia
Александр Ю. Смирнов Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997, Russia Skolkovo Institute of Science and Technology, 30/1 Bolshoi Blvd., Moscow 121205, Russia
Надежда С. Балеева Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997, Russia
Михаил С. Баранов Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997, Russia

DOI:

https://doi.org/10.1007/7348

Keywords:

oxazine oxo derivatives, oxazinoquinolinediones, titanium tetrachloride, amination, cyclization.

Abstract

A methodology was developed for the synthesis of 1-ethoxy-6-methyl-2H-[1,2]oxazino[3,4-c]quinoline-2,5(6H)-diones from methyl 4[2-(dimethylamino)phenyl]-5-ethoxy-6-oxo-6H-1,2-oxazine-3-carboxylates by the action of titanium tetrachloride under inert atmosphere. This interaction provides a rare example of demethylation followed by cyclization, yielding several new compounds.