SK29090A3 - £(5-substituted 4-oxo-4h-pyran-2-yl)methyl)chloro-acetates, method of their preparation - Google Patents

£(5-substituted 4-oxo-4h-pyran-2-yl)methyl)chloro-acetates, method of their preparation Download PDF

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SK29090A3
SK29090A3 SK29090A SK29090A SK29090A3 SK 29090 A3 SK29090 A3 SK 29090A3 SK 29090 A SK29090 A SK 29090A SK 29090 A SK29090 A SK 29090A SK 29090 A3 SK29090 A3 SK 29090A3
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Slovakia
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oxo
preparation
substituted
methyl
pyran
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SK29090A
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Slovak (sk)
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SK277933B6 (en
Inventor
Ruzena Cizmarikova
Eva Misikova
Jan Durinda
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Farmaceuticka Fakulta Uk Brati
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Publication of SK29090A3 publication Critical patent/SK29090A3/en

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Description

íŕ^a aľ 1-ôU· 7YX10- t/*k [(5-$uhiikLCva?w k-c*c--2-y<5) (\ Of^c-Och \d\ jjouj^tcic-^ŕ ^ a-1-ôU · 7YX10- t / * k [(5- $ uhlcLCva ?w k-c * c - 2-y < 5) (Of ^ c-Och jjjj ^ tcic- ^

OhCcijl^ 'ic.díyu tt'y-j ^ Yýiurkcjí. ;x\ Y y'4 ..v £<f5-/íllCMucíVí mjcý) 4 'OxQ-¥i-j^iC\'it·-2-jt )-»U A^· L^Ílk"(’U~Č to J C-1 (X ( C h t- y/C/jiy·OhCciIl ^ iIcIyuItIyIyyIcIycul. y y 4 .. lt ¥ ¥ j j C C C C C C C C C C C C C C C C C C C C C C ^ ^ ^ ^ ^ to J C-1 (X (C h t y / C / yy ·

JcĹL'tOjý ;jklt & H .Λϋίαη t f , 7 'lAUctiηχ! *<-<<'cc.-ui-n.tj '>iu Vč ^ f ulcÍtuiacc . ; .Ide o deriváty 5-hydroxy-2- hydroxymetyl-4-pyronu známeho ako kyselina kojová,ktorá vykazuje antibekteriálnuyantifungálnutprotizápalovú,insekticídmi účinnosť ako 1 kerdiotonickú a kardietoxickú aktivitu· V aúôaetnosti dosiahla najrozličnejšie využitie v kozmetike a i ako larvicíd ovocných a poľnohospodárskych Škodcov· .5?Ccloia(rru ^ *z<-u $--— / I I r / žu cyw ·’·ϊ * > lc [ /5-subs ti tu ovaň, ·' . -4-oxo-4H-pyrán-2-JcĹL'tOj; jklt & H .Λϋίαη t f, 7 'lAUctiηχ! * < - < < 'cc.-ui-n.tj' >; These are 5-hydroxy-2-hydroxymethyl-4-pyrone derivatives known as kojic acid, which exhibit antibacterial antifungal activity by insecticides as a potential and cardietoxic activity. ? Ccloia (rru ^ * from < -u $ --— / II r / zu cyw · '· ϊ * > lc [/ 5-subs ti ova, ·'. -4-oxo-4H-pyran-2 -

Pripravené látky môžu byť medziproduktami pre prípravu látok s biologickou aktivitou·Prepared substances can be intermediates for the preparation of substances with biological activity ·

Spôsob prípravy uvedených létok všeobecného vzorca I spočíva v tomtže na 5-subs ti tuované-2-h.ydroxyme ty 1-4-pyrony sa pôsobí chlóracetylchloridom v bezvodom xyléne pri teplote varu reakčnej zmesi počas reakčnej doby 9 hodín. lsodx^bnooti-f»rí^caay. £ ú JU v l edu-júfrospr i kla de · Μ f f y· · * ÁJicxci^ slíó\í tlcc ti-ťi (< __ 775-fjydro^^4-oxo~4H-py r én-2 -yl/me tyl] chl éra c e t é t 7,0 g /0,05mol/ kyseliny kolovej a 5,65 g /0,05mol/ chlórace-tylchloridu v 100 ml bezvodého xylénu sa zahrieva 9 hodín pod spätným chladičom.Počas zahrievania roztok tmavne a vylučuje sa tuhá látka.Po uplynutí reakčnej doby sa pevná látka odsaje a vákuovo sa oďdestiluje xylén.Do destilačného zvyšku sa pridá 100 ml vody a produkt sa vyextrahuje do chloroformu.The process for the preparation of the above-mentioned drugs of the formula I is based on 5-substituted-2-hydroxymethyl-4-pyrones with chloroacetyl chloride in anhydrous xylene at the reflux temperature of the reaction mixture for 9 hours. lsodx ^ bnooti-f »^ Sri ÇáäÝÓ. In the present invention, there is provided a pharmaceutical composition for use in the production of microcrystalline silicon dioxide (775-dihydro-2,4-oxo-4H-pyridin-2-yl) methyl. 7.0 g / 0.05mol / colloic acid and 5.65g / 0.05mol / chloroacetyl chloride in 100ml of anhydrous xylene are heated under reflux for 9 hours. After the reaction time, the xylene is suctioned off and vacuum-distilled. 100 ml of water are added to the distillation residue and the product is extracted into chloroform.

Po oddestílovaní chloroformu sa spojené pevné podiely prekryš-talizujú z etylacetátu a získa sa 60 % bielej látky^ teplote^c/ topenia 140-141°C.After distilling off the chloroform, the combined solids were recrystallized from ethyl acetate to give 60% of a white solid, m.p. 140-141 ° C.

Analýza pre CgHyO^Cl /M = 218,59/ vypočítané % C = 43,95., % H = 3,23., zistené % C - 44,05., % H = 2,03.Analysis for C 8 H 8 O 2 Cl / M = 218.59 (calculated% C = 43.95,% H = 3.23, found% C - 44.05,% H = 2.03).

Infračervené spektrum /nujol/ v/OH/ = 3150 -3500 cm“1 , = 3068 cm“1 , V1 /0=0/ = 1758,1656 cm“1 , )J/C=C/ = 1624C0T1, 1592 cm“1 , ^/COC/ = 1100-1300 cm“1. UV spektrum /etanol/= 218 nm /log£ = 4,23/., 273 nm /log £=3,90/ 1H-NMR h6 O ° 1 ^[r—- ch2o-c -ch2ciInfrared spectrum (nujol / v / OH) = 3150-3500 cm -1, = 3068 cm -1, V1 / 0 = 0 / = 1758.1656 cm -1, J / C = C / = 1624CT1, 1592 cm -1 1, ^ / COC / = 1100-1300 cm 1. UV spectrum / ethanol = 218 nm / log £ = 4.23 µ, 273 nm / log = = 3.90 / 1 H-NMR 6 0 ° 1 [[r - ch 2 O-c 2 -Cl 2]

o & = 4,16 ppm /CH20/ , 5,01 ppm /CHgCl/ , 6,54 ppm /H3/ , 7,87ppm /H6/. 13c-nmr = 40,30 ppm /CH2C1/ , 62,68 ppm /CH-O/ ,111,67 /C3/ ,137,88 /C / 145,92 /C5/ , 161^54 /000/ ,166,46 /07 ,172,70 /C4/. Týmto spôsobom bol pripravený [/5-metoxy-4-oxo-4Ií-pyI,án-2-yl/ metyl]chlóracetát. Teplota topenia 145“147°C Analýza pre CgH^Cl /M = 232,62/ vypočítané % C = 46,47 , % II =3,90 , zistené % C = 47,50 , % H = 4,10& = 4.16 ppm (CH 2 O), 5.01 ppm (CH 3 Cl 2), 6.54 ppm (H 3), 7.87 ppm (H 6). 13c-nmr = 40.30 ppm (CH 2 Cl 2), 62.68 ppm (CH-O), 111.67 (C 3), 137.88 (C / 145.92 / C5), 161-54 / 000 /, 166 , 46/07, 172.70 (C4). In this way, [5-methoxy-4-oxo-4H-pyridin-2-yl] methyl] chloroacetate was prepared. Melting point: 145 DEG -147 DEG C. Analysis for C9H11Cl2: M = 232.62 (calculated% C = 46.47% II = 3.90, found% C = 47.50,% H = 4.10)

Infračervené spektrum /nujol/ ΤΌΗΑγ/= 3068 cm“1 , ^/0=0/ 1758, 1656 cm"1 , V/C=C/ 1620,1596 cm"1 , *>/000/ 1300-1100. UV spektrum /etanol/ / = 216 nm /log č = 4,16/ , 268nm /log £_Infrared / nujol / ΤΌΗΑγ / = 3068 cm -1, 1/0 = 0/1758, 1656 cm " 1, V / C = C / 1620.1596 cm " 1, * > / 000 / 1300-1100. UV spectrum / ethanol = 216 nm / log n = 4.16, 268 nm / log £.

UluJL = 3,93/UluJL = 3.93 /

Claims (2)

1. r γ 'VfrlENTO'fä MKO£Yf [ /5-Substituované-4-oxo-4H-pyrón-2-yl/metyl] chlórocetáty všeobecného vzorca I1. The compound of the formula [5-Substituted-4-oxo-4H-pyron-2-yl] methyl] chloroacetates of the formula I - CH20C0CH2C1 BCH20C0CH2C1 B I kde E znaceend hydroxy a aetoxy. jjc ta\í(í Λ>" -Htl ÍY&U iI where E is hydroxy and aethoxy. í gt gt í í í í í í í í í í í í í 2. Spôsob prípravy {./^-substituovaných -4-*oxa-4iÍ-Tpyrán-2-yl/ -- φ * ‘i ltť·"4 ^V/ {£ znetyljchluracstátov všeobecného vzorca I^vyznačujúci sa tým,*e nechá reagovať príslušný 5-substi tuovaný-2-hyd-.roxyoetyl-4-pyron s chloracetylchioridom v bezvodoai xyléne pri teplote vami reakčnej zases! po dobu 9 hodín. / ~O ΓΟ O O 03 *< u. -z n >- < r--< ΓΠ J\J -< O 33< f\> •NJ · '.O O t O/ o· ©J f* í i ClivelCL& r v Λ, olív "/* -Líčio /Ho *oc Y ν 'Ψ U1 £[*-ĹL ' * 5-4mbstituované-4~oxo-4H-p.vrán~2-yl/gietyl chlórecetót£4 8 spôsob' ich prípravy , 2-yl/metyl3 chlóracetáty /5-^ufcs ti tuovsniiľ- 4-cx.o-4H-pyrán-všeobecného vzorca X2. A process for the preparation of N-substituted-4-oxa-4-yl-pyran-2-yl / 4-oxo-4'-methylthiocrystalline compounds of formula (I) wherein: allowing the corresponding 5-substituted-2-hydroxyethyl ethyl-4-pyrone to react with chloroacetyl chloride in anhydrous xylene at the temperature of the reaction mixture. for 9 hours. / O O O 03 * < u. -z n > - < R - < JΠ J J - < O 33 < f \ > • NJ · .O O t o / o © * ClivelCL & Λ, ív, ív, ív, ív, ív, ív, ív, ív, ív, ív, ív, ív, ív, ív, ív, ív, ív, ív, ív, ív, ív, ív, ív, -4, -4, -4, -4 their preparation, 2-yl / methyl-3-chloroacetates / 5-fluoro-4-oxo-4H-pyran-formula X CH20C0CH2G1 ) E —CH20C0CH2G1) E - 0 kde F je hydroxy a amtoxy^/sfiZ/b / ,:j\· /<- u 'f-'L a/icjt i ' '' rea.^acít. 5-sub- s ti tuovam^-hydroxyaetyl-4-pyrórv v s chlórace tylchl oridoai V bezvodom xylíne pri teplote varu reaxenej zjiesi po dobu 9 hodín.Uvedené látky ;nô2u byť uedziproduktaai pre prípravu látok s biologickou aktivitou.Where F is hydroxy and amtoxy ^ / sfiZ / b /; 5-Substituent-4-hydroxy-ethyl-4-pyrrolidine chlorination of tylchloride in anhydrous xylene at the boiling point of reconstituted for 9 hours. The above-mentioned compounds can be produced for the preparation of substances with biological activity. L· C í ÍL LLV'/í Ĺ L ( ' ľ Í/ c/ — Q OLL í V V ((((((((((((((((((((((((((((O O O O O O O O O O CH.0C0CHoCl c 2 IO CH 2 OCH 2 CO 2 Cl 2 I
SK29090A 1990-01-22 1990-01-22 £(5-substituted 4-oxo-4h-pyran-2-yl)methyl)chloro-acetates, method of their preparation SK29090A3 (en)

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CS29090A2 (en) 1991-08-13

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