SU615071A1 - Method of obtaining 2-phenacylidenebenz-1,4-thiazinones-3 - Google Patents

Method of obtaining 2-phenacylidenebenz-1,4-thiazinones-3

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Publication number
SU615071A1
SU615071A1 SU752154320A SU2154320A SU615071A1 SU 615071 A1 SU615071 A1 SU 615071A1 SU 752154320 A SU752154320 A SU 752154320A SU 2154320 A SU2154320 A SU 2154320A SU 615071 A1 SU615071 A1 SU 615071A1
Authority
SU
USSR - Soviet Union
Prior art keywords
obtaining
thiazinones
phenacylidenebenz
thiazinone
mol
Prior art date
Application number
SU752154320A
Other languages
Russian (ru)
Inventor
Юрий Сергеевич Андрейчиков
Светлана Петровна Тендрякова
Юлия Аркадьевна Налимова
Лидия Андреевна Воронова
Original Assignee
Пермский государственный фармацевтический институт
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Application filed by Пермский государственный фармацевтический институт filed Critical Пермский государственный фармацевтический институт
Priority to SU752154320A priority Critical patent/SU615071A1/en
Application granted granted Critical
Publication of SU615071A1 publication Critical patent/SU615071A1/en

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Description

Изобретение относитс  к новому спо собу получени  новых производных 1,4-тиазинона-3 , которые могут найти при менение в качестве исходных продуктов дл  синтеза биологически активных веществ . Известен способ получени  2-бензилиденбенз-1 ,4-тиазинонов-З циклизацией S -замещенных производных о-аминотиофенолов с образованием оксибензотиазепинона и изомеризацией его при обработке тионилхлоридом в присутствии пиридина ||l . Указанный способ не позвол ет получать производ ные 1,4-тиазинона-З, содержащие в 2-положении фенацилиденовый остаток. Целью изобретени   вл етс  способ получени  производных 1,4-тиазинонов-З , содержащих в положении 2 фена . цилиденовый остаток. Поставленна  цель достигаетс  спо собом получени  2-фенацилиденбенз-1 ,4-тиазинонов-З общей формулы Ч;; хЧ х ИСОАГ f г-де А г - фенил, п -тол л, tt -мет оксифенил, 11 -этилфенил, к -хлорфенил или Н -бромфенил. Способ заключаетс  в том, что О-аминотиофенол подвергают взаимодействию с ароилпировиноградной кислотой общей формулы II АнСОСН.,,СОСООН где А г имеет указанные значени , при температуре 95-105 С в диоксане. При мер 1. 2-Фенанцилиденбенз-1 ,4-тиазинон-З. Смесь 1 г (0,005мол ) бензоилпировиноградной кислоты и 0,4г (0,005 мол ) О -аминотиофенола в 100 мл диоксана нагревают при температуре 95-105 С в течение 1,5 ч. После удалени  растворител  получают 1, г (72%) продукта с т.пл. 182 С (изопропиловый спирт) Найдено,%: N 4,7; 6 10,3. С1бНцИ02б., Вычислено, %: VI 4,68; S 10,6. П р и м е р 2. 2-(4-Метилфенацилицен ) бенз- 1,4-тиазинон-З. Х0,0048мол ) tt -метилбензоилпировиноградной кислоты и (0,0048 мол ) О -аминотиофенола нагревают при температуре 95 .105с в 100 М.П диоксана в течение 1,5 ч. После удалени  растворителпThe invention relates to a novel process for the preparation of novel 1,4-thiazinone-3 derivatives, which can be used as starting materials for the synthesis of biologically active substances. A known method for producing 2-benzylidenebenz-1, 4-thiazinone-3 by cyclization of S-substituted derivatives of o-aminothiophenols with the formation of oxybenzothiazepinone and isomerization of it when treated with thionyl chloride in the presence of pyridine || l. This method does not allow obtaining 1,4-thiazinone-3 derivatives containing in the 2-position a phenacylidene residue. The aim of the invention is a method for producing 1,4-thiazinone-3 derivatives containing phen in position 2. cilidene residue. This goal is achieved by the method of obtaining 2-phenacylidenebenz-1, 4-thiazinones-3 of the general formula H ;; xCH x ISOOF f r-de A g - phenyl, p-tol l, tt -methoxyphenyl, 11-ethylphenyl, c -chlorophenyl or H-bromophenyl. The method consists in the fact that O-aminothiophenol is reacted with aroyl pyruvic acid of general formula II AnSOCN, CO 2 CO 2 where A g has the indicated values, at a temperature of 95-105 ° C in dioxane. Example 1. 2-Phenancilidebenz-1, 4-thiazinon-3. A mixture of 1 g (0.005 mol) of benzoyl pyruvic acid and 0.4 g (0.005 mol) of O-aminothiophenol in 100 ml of dioxane is heated at a temperature of 95-105 ° C for 1.5 hours. After removing the solvent, 1, g (72%) of product is obtained from m.p. 182 С (isopropyl alcohol) Found:% 4.7; 6 10.3. С1бНцИ02б., Calculated,%: VI 4.68; S 10.6. Example 2. 2- (4-Methylphenacylcene) benz-1,4-thiazinone-3. X0.0048 mol) tt -methylbenzoyl pyruvic acid and (0.0048 mol) O-aminothiophenol are heated at a temperature of 95.105 s in 100 MP of dioxane for 1.5 hours. After removal of the solvent

SU752154320A 1975-07-08 1975-07-08 Method of obtaining 2-phenacylidenebenz-1,4-thiazinones-3 SU615071A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
SU752154320A SU615071A1 (en) 1975-07-08 1975-07-08 Method of obtaining 2-phenacylidenebenz-1,4-thiazinones-3

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SU752154320A SU615071A1 (en) 1975-07-08 1975-07-08 Method of obtaining 2-phenacylidenebenz-1,4-thiazinones-3

Publications (1)

Publication Number Publication Date
SU615071A1 true SU615071A1 (en) 1978-07-15

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Application Number Title Priority Date Filing Date
SU752154320A SU615071A1 (en) 1975-07-08 1975-07-08 Method of obtaining 2-phenacylidenebenz-1,4-thiazinones-3

Country Status (1)

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SU (1) SU615071A1 (en)

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