CS232192B1 - 1,2-Dihydro-1,2,4-triazino [< 5 &gt;, 5 &apos;: 1, 53 pyrrolo, 3: 4,5 &lt; / RTI &gt; - Google Patents

Abstract

The invention relates to the field of organic chemistry and relates to the preparation of new compounds of 1,2-dihydro-1,2-4-triaminol*»,5'»:1J ,5J pyrroloΓ2 *,3 · :4,5] furo |3,2-0indol-1-ones. The essence of the method for the preparation of the compounds according to the invention is that 1,9-dihydropyrrolo[2*,3·:4,5Jfuro[3,2-bl indole-2-carboxyl acid hydrazide is heated and triethyl ester of orthoaravic or orthoacetic acid in dimethylfuroamide at a temperature of 100-153 C. The compounds according to the invention belong to a new group of condensed heterocycles both of which contain a furan nucleus and can be used as starting materials for vigorous types of heterocyclic compounds 1,2-Dihydro-1,2,4-triazinoΓ4'·JJ”:1,,5'J,pyrrolo-t2,,3':4,0furo [5,2-b) indol-1-ones characterized by the formula

Description

The essence of the method for preparing 1^-dihydro-1^a-triazino[Í ¹ , 5 * ': 1 *, 5 pyrrolo [2 ',3 ': 4 > £ furo [3,2-b] indol-1-ones of formula I consists in treating 1 _r 9-dihydropyrrolo[Î',3'rt.3 furo [3,2-b]indole-2-carboxylic acid hydrazide; ao 23034 2. formula II with triethyl ester of orthoformate or orthoacetic acid in dimethylformamide at a temperature of 100 - 153°C.

The advantages of the method of preparing the compounds according to the invention lie, among other things, in the fact that the synthesis is a single-step process, carried out in simple apparatus with good yields.

1.2-Dihydro-1,2,4-triazino[4* ^> ,5''*il*t5*]pyrrolo[2^,3/:4.,5]furo[3,2-bIndol-1-ones have wide applications as various reaction components in organic synthesis. They react with phosphorus pentasulfide to the corresponding thiones, with phosphorus trichloride to chloride derivatives. They also provide the possibility of condensing another heterocyclic ring.

The subject matter of the invention is illustrated, but not limited, by the following examples:

Example 1

1.2- Dihydr©-1,2,4-triazine J<**,5** tl*»5*Jpyrolo β',3*:4,5] furo[3,2-bJindol-1-ott

1,9-Dihydropyrrolo[2*,3'54,5] furo[3,2-b] indole-2-carboxylic acid hydrazide (2.54 g, 0.01 mol) and orthoformate triethyl ester (2^0 g, 0^014 mol) in dimethylformamide (10 ml) are heated at boiling point for 2.5 h^j. After cooling, the precipitate is filtered off with suction and crystallized from dimethylformamide.

- 3Example 2

232 192

indole-2-carboxylic acid (2/54 g, 0/01 mol) and orthoacetic acid triethyl ester (1/8 g, 0/011 mol) are heated at boiling point for 3 hours. The solvent is distilled off in vacuo and the residue is recrystallized from dimethylformamide.

The structure of the compounds was proven by elemental analysis / Table 1 / and IR and ¹ H HUS spectra / Table II /.

Spectral measurements

Infrared spectra were measured on a spectrophotometer!

SPECORD 71IB / Carl Zeiss Jena/. NMR spectra were measured on an 80 MHz spectrometer! BS 487 C Tesla in hexadeuterodimethylsulfoxide using an internal standard of hexamethyldisiloxane,

- 4,232,192

Table I

1,2-Dihydro-1,2»4-triazino [< * » ,5 ’ *: 1 * »Pyrrolo furo ^,2-bjindol-1-ones

Compound Sum. formula Was wt. M.t. °G Yield % Slementary analysis calculated / found SBC SIB %K I and ^C 14% ^H 4°2 230 years 63.63 3.05 21.20 R x H 264.2 79 63.48 2.93 21.10 I b ^C 15 ^H 1O ^N 4°2 255 years 64.74 3.62 20.13 R = CHy 278.3 76 64.60 3.53 20.32

Table II

IR and ¹ H NMR spectra of compounds 1a, 1b.

Compound R ^=0 £/ noa / In *12 Charm at _{4 o'clock} - _{at 3 o'clock} ¹ ® H 1651 cm" ¹ 8,T9d 7.29d 7.00 - 7.75m ^{1 point} CH ₃ 1655 cm" ¹ - 7.17® 7.07 - 7.80» 2.86a

For R = H 0.8 Hz

Claims (2)

SUBJECT OF THISXLEZU 232 192 1 l, 2-dihydro-l, 2,4-triazin ^ '* _R ** 5 .mu.l *, 5 R] _ pyw> lo | ^2', 3 ': 4,5 bar ^ © | 3,2-bJindol The 1-ones of formula (I) are: where N is H 2. Spdsob preparation of _L> 2-dihydr®-l, 2-triazine _° 4 * 1 ', 5 »pyrrolo J | ^ 2 + _T 3 * 14> 5j ^ uro ^, 2-bjindol-l-ones, Come point 1. characterized in that to the 1,9-dihydropyrrolo: 4,5-phenoxy-3,2-bindole-2-carboxylic acid hydrazide of the formula II: H ('( ^JI ) is treated with triethyl esters of orthoformic or ortho-acetic acid in dimethylformamide at a temperature of 100-153 ° C.