SU475774A3 - The method of obtaining quinazoline derivatives - Google Patents

The method of obtaining quinazoline derivatives

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Publication number
SU475774A3
SU475774A3 SU1754058A SU1754058A SU475774A3 SU 475774 A3 SU475774 A3 SU 475774A3 SU 1754058 A SU1754058 A SU 1754058A SU 1754058 A SU1754058 A SU 1754058A SU 475774 A3 SU475774 A3 SU 475774A3
Authority
SU
USSR - Soviet Union
Prior art keywords
quinazoline derivatives
obtaining
formula
obtaining quinazoline
acids
Prior art date
Application number
SU1754058A
Other languages
Russian (ru)
Inventor
Инаба Сигехо
Ямамото Митихиро
Исизуми Кикуо
Мори Казуо
Косиба Масао
Ямамото Хисао
Original Assignee
Сумитомо Кемикал Компани Лимитед (Фирма)
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Сумитомо Кемикал Компани Лимитед (Фирма) filed Critical Сумитомо Кемикал Компани Лимитед (Фирма)
Application granted granted Critical
Publication of SU475774A3 publication Critical patent/SU475774A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
    • C07D239/80—Oxygen atoms
    • C07D239/82—Oxygen atoms with an aryl radical attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Description

бром н йод. Группа алкилена, представленна  формулой С„Н2,|, включает, например, метилен, этилен, 1-метилэтилен, 2-метилэтилен и триметилен. По предлагаемому способу производные хиназолина общей формулы (I) получают нагреванием соединений общей формулы (II) CriHjii RK . r-N-CONH,, СН-ОН в которой RI, Ra, Ra, R и   имеют указанцые выше значени , в присутствии кислоты. Примерами используемых дл  данной цели кислот  вл ютс  неорганические кислоты, такие как серна  и хлористоводородна , и органические кислоты, такие как уксусна  и т. д. Реакци  обычно протекает в интервале температур от 90 до 120°С. Пример. К раствору 2,9 г 2-(2-этоксиэтиламино )-5-хлорбе)Нзгидрола в 30 мл уксуснои кислоты дооавл ют 0,9 г цианата кали . Смесь перемешивают и нагревают до кипени . После охлаждени  смесь разбавл ют водой , экстрагируют хлороформом. Экстракт промывают разбавленным водным раствором гидрата окиси натри , водой и высушивают над безводным сульфатом натри . Растворитель удал ют при Пониженном давлении и остаток перекристаллизовывают из этанола. В результате получают 1-(2-этоксиэтил)-4фенил-6-хлор-3 ,4 - дигидро-2-(1Н) -хиназолинплавлени  127- он, имеющий температуру 128,5°С. где R представл ет собой низщлй циклоалкил , тригалоидометил, низший алкоксил, низШий тиоалкил, низший алканоилоксил или группу формулы -NRsRe или -CONiRsRe ( где каждый из радикалов Rs и Re представл ет собой низший алкил, при условии, что RS и Re могут образовывать вместе со смежным атомом азота незамещенное или замещепиое п ти- или шсстичленное гетероциклическое кольцо, которое может включать, кроме того, атом азота, кислорода или серы); каждый из радикалов Ri и R2-атом водорода , низший алкил, низший алкоксил, нитрогруппа , трифторметил, низший тиоалкил. низший алкилсульфонилрадикал или атом галогена; RS - группа формулы ( в которой R4  вл етс  атомом водорода, низшим алкилом , низшим алкоксилом, трифторметилом или атомом галогена), нафтил, низший циклоалкил , «изший циклоалкенил, пиридил. пирролил, тиенил, или фурилрадикал; п - целое число от 1 до 3, тличающийс  тем, что соединение щей формулы (II) В- СпН-д, I -Т -СОКНгbromine n iodine. The alkylene group represented by the formula C H2, |, includes, for example, methylene, ethylene, 1-methylethylene, 2-methylethylene and trimethylene. According to the proposed method, quinazoline derivatives of general formula (I) are obtained by heating compounds of general formula (II) CriHjii RK. r-N-CONH ,, CH-OH in which RI, Ra, Ra, R and have the above values, in the presence of acid. Examples of acids used for this purpose are inorganic acids, such as sulfuric and hydrochloric acids, and organic acids, such as acetic acids, etc. The reaction usually takes place in the temperature range from 90 to 120 ° C. Example. 0.9 g of potassium cyanate was added to a solution of 2.9 g of 2- (2-ethoxyethylamino) -5-chlorbe) Nzhydrol in 30 ml of acetic acid. The mixture is stirred and heated to boiling. After cooling, the mixture is diluted with water, extracted with chloroform. The extract is washed with a dilute aqueous solution of sodium hydroxide solution, water, and dried over anhydrous sodium sulfate. The solvent is removed under Reduced pressure and the residue is recrystallized from ethanol. The result is 1- (2-ethoxyethyl) -4phenyl-6-chloro-3, 4 - dihydro-2- (1H) -quinazoline 127-one, having a temperature of 128.5 ° C. where R is lower cycloalkyl, trihalomethyl, lower alkoxy, lower thioalkyl, lower alkanoyloxy or a group of the formula -NRsRe or -CONiRsRe (where each of the radicals Rs and Re is lower alkyl, provided that RS and Re can form together with an adjacent nitrogen atom, unsubstituted or substituted for five- or shstechennaya heterocyclic ring, which may include, in addition, a nitrogen atom, oxygen or sulfur); each of the radicals Ri and R2 is a hydrogen atom, lower alkyl, lower alkoxy, nitro, trifluoromethyl, lower thioalkyl. lower alkylsulfonyl radical or halogen atom; RS is a group of the formula (in which R4 is a hydrogen atom, lower alkyl, lower alkoxy, trifluoromethyl, or halogen atom), naphthyl, lower cycloalkyl, "extra cycloalkenyl, pyridyl. pyrrolyl, thienyl, or furyl radical; n is an integer from 1 to 3, different from the fact that the compound of formula (II) is B-Cn-d, I -T is COKNg

Предмет изобретени Subject invention

1. Способ получени  производных хиназолина обшей формулы (I)1. A method for producing quinazoline derivatives of the general formula (I)

где R, RI, R2, Ra и п имеют указанные выше значени ,where R, RI, R2, Ra and p are as defined above,

подвергают нагреванию в присутствии органической или неорганической кислоты с последующим выделением целевого продукта обычным методом.subjected to heating in the presence of an organic or inorganic acid, followed by isolation of the target product by the usual method.

2. Способ по П. 1, отличающийс  тем, что процесс ведут при температуре 90-120°С.2. The method according to claim 1, characterized in that the process is conducted at a temperature of 90-120 ° C.

SU1754058A 1970-12-23 1971-06-12 The method of obtaining quinazoline derivatives SU475774A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP11833270A JPS4834598B1 (en) 1970-12-23 1970-12-23

Publications (1)

Publication Number Publication Date
SU475774A3 true SU475774A3 (en) 1975-06-30

Family

ID=14734027

Family Applications (1)

Application Number Title Priority Date Filing Date
SU1754058A SU475774A3 (en) 1970-12-23 1971-06-12 The method of obtaining quinazoline derivatives

Country Status (6)

Country Link
JP (1) JPS4834598B1 (en)
AT (2) AT310178B (en)
CH (2) CH563995A5 (en)
CS (2) CS181693B2 (en)
ES (2) ES419267A1 (en)
SU (1) SU475774A3 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PT1122253E (en) * 1998-10-16 2005-11-30 Sumitomo Pharma QUINAZOLINONE DERIVATIVES

Also Published As

Publication number Publication date
AT310177B (en) 1973-09-25
AT310178B (en) 1973-09-25
CH563995A5 (en) 1975-07-15
JPS4834598B1 (en) 1973-10-22
CS181665B2 (en) 1978-03-31
ES419266A1 (en) 1977-01-01
SU439980A3 (en) 1974-08-15
CH564539A5 (en) 1975-07-31
CS181693B2 (en) 1978-03-31
ES419267A1 (en) 1976-11-01

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