SU553248A1 - Method for producing 1,3-dihydrothieno (3,4-b) indoles - Google Patents

Description

in ether or alcohol saturated with hydrogen chloride, and after a rapid dissolution of the reagents (1-2 minutes), the properties of the compounds fhm лыmuly 1, where Rj - - CHj and H - «H, are listed in Table. I,

In the case of water or water, the hydrochloride of 1,1- R, .U 4 and the 3 (3,4-b) -indoles with ammonium are separated by water-insoluble scientific research institutes, and the chemical reactions that are reactive Fushshish groups, in particular, they adv-gall on the imino group and hydrolyze with the formation of 1,1-R, 1 2-thie H1 - (3,4-JD) n-dolons -3 {see Table 2 and Table. 3). Stroe Che 1.1. 4-iminothieno (3j.4-b) - "ndo" 1 was confirmed by PMR, IR and UV spectroscopy.

The UV spectrum of all compounds, except for co-form with form 1 Ш1 Г, where Н иТ ,, - п-N () has I max area 3-02-ЗО6 nm (4.65), which is close to the position I max. OO ny 4,6O) for 1-me1SH1Iy sh1-2- “arbonskoy acid.

The KK-spectrum of compounds isolated as a base contains a band of 1610 1615 cm of transmission and intensity (stretching vibrations: С 1 «) and a clock in the 3210 area {valeN1 alley р ebani N -H).

Example 1, Chl rpyvdrat 1-phenyl-. -Z-go-4-methi -1, igidrotieno

- (3,4-bJ - indole

To a mixture of 0.19 g (O, OO, 1 g-mol) tiovmnd 1-: methyl or 2-ced 6onovoy. acids

crystal 1G x; whom the amount of chlorine of the target schuduct is given.

The reaction proceeds according to the scheme:

SH-H01

and 0.1O6 g (0.001 g-mol) of benzaldehyde was added 5 ml of alcohol saturated with hydrogen chloride. The mixture dissolves with stirring and after 2-3 minutes a precipitate begins to form. Yield 0.298 g (95%); m.p. 222 C.

The PMR spectrum contains an aromatic multiplet - 9H; 7.20 ml, N —CH. - singleg ZN; 4, O6 ppm benzylgene proton singlet IH; 6, O4 lm.

0.25 g of hydrochloride is dissolved in 5 ml of 7O% aqueous solution of sodium hydroxide, iodine-saturated with aqueous ammonia, the precipitate is filtered off, washed with water and crystallized from alcohol. Output O, 2O g (78%); m.p. 2OZ C. Chromatography on silufol in the cyclohexane-ethyl acetate system (3: 1) gives one spot with 4f P, 6O.

PRI mme R 2. Chlorohydrate 1,1ndambityl-3-imine of o-4-meta-1 l-1,3-dihydrogt eno- (3,4-b) - indole.

To a mixture of 0.19 g (p, OO1 g mol) of 1-methyl alcohol of 2-carboxylic acid and O, 58 g (d, 01 g-mol) of thioamide. 3 ml of ether saturated with hydrogen chloride are added to the acetate. 1-2 hours of the year of the comet, the temperature is suitable, and the walls of the rice are tall and filtered. Yield Q, 24 g (90%); Gil. 24O C.

Claims (1)

The PMR spectrum suppresses aromatic protons - 4H; 7.2 m, d, - СНд - ЗН; 3.71 M.D. , heme-ymethyl group - 6H; -. 1.71 .M.D. Claims 1. Method for producing 1,3-dihydrothieno {3, 4-b) -indoloB of general formula. 3 where I, is hydrogen or alkyl; R. hydrogen, alkyl, arylalkyl, aryl alkenyl or 2-furyl, or R and 7 together start a radical (j CHrtjn where P 4-5; alkyl; T is hydrogen or acetyl, characterized in that the thio amide is 1-alkylindol-2 -carboxylic acid is reacted with a compound of the general formula where RI and R are as defined above, in organic solvents saturated with hydrogen chloride, with the following isolation of the desired product as a salt or base, or, in the case when TJ.-acetyl, the resulting base is acylated .