CS232192B1 - l,2-Dihydro-l,2,4-triazino[<’»,5”:l»,53 pyrolo ,3 :4,5^fůro j3,2-bjindol-l-óny a eposob ich přípravy - Google Patents
l,2-Dihydro-l,2,4-triazino[<’»,5”:l»,53 pyrolo ,3 :4,5^fůro j3,2-bjindol-l-óny a eposob ich přípravy Download PDFInfo
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- CS232192B1 CS232192B1 CS533083A CS533083A CS232192B1 CS 232192 B1 CS232192 B1 CS 232192B1 CS 533083 A CS533083 A CS 533083A CS 533083 A CS533083 A CS 533083A CS 232192 B1 CS232192 B1 CS 232192B1
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Description
Podstata spdsobu přípravy l^-dihydro-l^á-triazíno[Í1 , 5 * ’: 1 *, 5 pyrolo [2 ’ ,3 ’: 4 > £ fůro [3,2-b] indol-l-onov vzorca I spočívá v tom, že sa na hydrazid kyseliny lr9-dihydropyrolo[Ž’,3’rt.3 fůro [3,2-b]indol-2-karboxylovej; ao 23034 2. vzorca II pdsobí trietylesterom kyseliny ortomravč ěJ alebo ortooctovej v dimetylfomamide pri· teplote 100 - 153°C·
Výhody spdsobu přípravy zlúčenín podlá vynálezu spočívajú okrem iného v tom, že syntéze je jednostupňová, uskutečňuje sa v jednoduchéj aparatúre 3 dobrými výťažkami.
1.2- Dihydro-l,2,4-triazíno|4*>,5’'*íl*t5*] pyrolo [2^,3/:4.,5] fůro [3,2-bJindol-l-ony majú široká pemžitie ako rdzno reakčné komponenty v organickej syntéze. Reagujú s pentasulfidem fosforečným na korešpondujúee tióny, s trichloridom ^fosforečným na chlprderiváty. Taktiež poskytujú možnosť prikondenzovania ďalšieho heterocyklického kruhu.
Predmet vynálezu ilustrujú, ale neobmedzujú následovně příklady:
Příklad 1
1.2- Dihydr©-l,2,4-triazíno J<**,5** tl*»5*Jpyrolo β’,3*:4,5] fůro[3,2-bJindol-l-ott
Hydrazid kyseliny 1,9-dihydropyrolo^2*,3’54,5] fůro[3,2-b] indol-2-karboxylovej /2,54 g, Q,01 mol/ a trietylester kyseliny ortomravčej /2^0 g, 0^014 mol/ v dimetylformamide /10 ml/ sa zahrieva pri teplote varu po dobu 2,5 h^jí. Po ochladení sa zrazenina odsaje a krystalizuje z dimetylformamidu.
- 3Příklad 2
232 192
indol-2-karboxylovej /2/54 £» 0/01 mol/ a trietylester kyseliny ortooetovej /1/8 g, 0/011 mol/ sa zahrieva pri teplote varu po dobu 3 hodin. Rozpúáťadlo sa vákuov© oddestiluje a zvyšok sa prekryš táli zu je z dimetylformamidu.
Štruktúra zlúšenín bola dokázané elementárnou analýzou / tab. 1/ a IR a 1H HUS spektrami / tab. II/.
Spektrálná merania
Infračervená spektrá sa namerali na spektrofotometr!
SPECORD 71IB / Carl Zeiss Jena/. NMR spektrá boli naměřené na 80 MHz spektrometr! BS 487 C Tesla v hexadeuterodimetylsulfoxide za použitia vnútorného Standardu hexametyldisiloxánu,
- 4 232 192
Tabulka I
1,2-Dihydro-1,2»4-triazíno [< * » ,5 ’ *: 1 * »Pyrolo fůro ^,2-bjindol-l-ony
| Zlúčenina | Sum. vzorec Bol hm. | T.t. °G Výťažok % | Slementáma analýza vypočít. / nójdené | ||
| SBC | SÍB | % K | |||
| I a | C14%H4°2 | 230 r | 63,63 | 3,05 | 21,20 |
| R χ H | 264,2 | 79 | 63,48 | 2,93 | 21,10 |
| I b | C15H1ON4°2 | 255 r | 64,74 | 3,62 | 20,13 |
| R = CHy | 278,3 | 76 | 64,60 | 3,53 | 20,32 |
Tabulka II
IR a 1H NMR spektrá zlúčenín la, Ib.
| Zlúčenina | R | ^=0 | £/ noa / | |||
| V | *12 | ®arom | o4-ot3 | |||
| 1 ® | H | 1651 cm“1 | 8,T9d | 7,29d | 7,00 - 7,75m | |
| 1 b | CH3 | 1655 cm“1 | - | 7,17® | 7,07 - 7,80» | 2,86a |
Pre R = H 0,8 Hz
Claims (2)
- PREDMET TThXlEZU232 1921. l,2-Dihydro-l,2,4-triazíno ^’*r5**íl*,5^]_pyw>lo|2,,3‘:4,5^ far© |3,2-bJindol-1-ony všeobecného vzorca I ík ^Nx ftffcbo ci kde R je H
- 2. Spdsob přípravy l>2-dihydr®-l,2ř4-triazíno * :1» ,5»J pyrolo |^2* T3* 14>5j ^uro ^,2-bjindol-l-onov podTa bodu 1. vyznačený tým, že sa na hydrazid kyseliny 1,9-dihydropyrolo:4,5j fa^o j3,2-bJindol-2-karboxylovej vzorca IIHΝ' (JI) pdsobí trietylestermi kyseliny ortomravčej alebo ortooetovej v dimetylformamide pri teplote 100 - 153*0.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS533083A CS232192B1 (cs) | 1983-07-15 | 1983-07-15 | l,2-Dihydro-l,2,4-triazino[<’»,5”:l»,53 pyrolo ,3 :4,5^fůro j3,2-bjindol-l-óny a eposob ich přípravy |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS533083A CS232192B1 (cs) | 1983-07-15 | 1983-07-15 | l,2-Dihydro-l,2,4-triazino[<’»,5”:l»,53 pyrolo ,3 :4,5^fůro j3,2-bjindol-l-óny a eposob ich přípravy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS232192B1 true CS232192B1 (cs) | 1985-01-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS533083A CS232192B1 (cs) | 1983-07-15 | 1983-07-15 | l,2-Dihydro-l,2,4-triazino[<’»,5”:l»,53 pyrolo ,3 :4,5^fůro j3,2-bjindol-l-óny a eposob ich přípravy |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS232192B1 (sk) |
-
1983
- 1983-07-15 CS CS533083A patent/CS232192B1/cs unknown
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