SU632191A1 - Pyridazine-(3,4-b)-indole derivatives and method of obtaining same - Google Patents

Abstract

1. Derivatives of iridazino

Description

The invention relates to new chemical compounds - derivatives of pyridazino- (3,4-b) -indole of the formula general

N — Ar

where Ar is phenyl or η-tolyl, and the method for their preparation.

These compounds can be found as physiologically active substances.

A known method for producing 3-phenyl-9H-pyridazino- (3,4-b) -indole of the general formula

where R is hydrogen or lower alkyl ζ X halogen, lower alkyl or alkoxy, hydrogen, trifluoromethyl, which consists in the fact that 2,3-dioxyindoline-carboxylic-7 acids are converted to 3-hydroxy-3-phenacyl-2-oxo compounds followed by dehydration of the latter and ring closure using hydrazine [1].

The aim of the invention is to obtain a new class of chemical compounds containing a new combination of known types of bonds between two heterocyclic nuclei - indole ¹ and pyridazine.

A method for producing pyridazino- (3,4-b) -indole derivatives is that 1-methyl-3-arylazoindolip-2-acetic acid ethyl ester is of general formula 40

СН ₂ СООС _g Н5

CH ₃ where Ar has the above meanings, is subjected to cyclization with caustic alkali 55 in an alcoholic medium at boiling.

VNIIPI Order 92/2 ______________

Branch SHSh * 'Patent ⁿ , g ”Uzhhorod, Project 4,

The resulting compounds are colorless crystalline substances, readily soluble in lower alcohols, chloroform, etc. them 212219 ° C.

The structure of compounds of the general formula (1) is proved by the data of YK-, PMR-, mass spectra.

Example 1. 2, 3-Dihydro-2-phenyl-3-keto-5-methylpyridazino (3,4-b) -indole.

A solution of 1.6 g (0.005 mol) of 1-methyl-3-phenylazoindolyl-2-acetic acid ethyl ester and 1 g of sodium hydroxide in 50 ml of alcohol is boiled for 30 minutes. Then the alcohol is evaporated in vacuo, the precipitate formed is filtered off, washed with water and recrystallized from alcohol. The yield of 1.1 g (81%), so pl. 217-219 ° C (from alcohol).

Found,%: C 74.11 H 4.8;

15.4

Ο ^ Η ^ Ν, Ο

Calculated,%: C 74.2 J H 4.8;

15.3

IR spectrum, cb ¹ (KBr); 1660, 1630 (C = 0, amide).

In the mass spectrum, the molecular ion (M) ⁺ = 275. In the PMR spectrum, a singlet signal at 6.33 ppm belonging to the H ₄ proton and signals of aromatic protons (9H) in the region

7.5-7.9 ppm

Example 2. 2,3-Dihydride ρο-2-η-tolyl-3-keto-5-methylpyridazino- (3,4-b) -indole.

This compound is prepared according to Example 1 from 1.7 (0.005 mol) of 1-methyl-3-p-tolylazoindolyl-2-acetic acid ethyl ester and 1 g of sodium hydroxide in 50 ml of alcohol. Yield 1.2 g (83%), mp 212 ° C (from alcohol).

Found,%: C 74.9; H N 14.6

C16 NjO Calculated

N 14.5

IR spectrum, (C = 0, amide).

In the mass spectrum there is a molecular ion (M) ⁺ - 289.

In the PMR spectrum, a singlet signal at 6.35 ppm belonging to the proton H ^ and signals of aromatic protons (8n) in the region of 7.02-7.95 ppm are observed.

Circulation 384 Subscription

5.4;

Η 5.2, cm ^-1 (KBr):

1670, 1630

Claims (2)

PYRIDAZINO- (3,4-b) INDOLA DERIVATIVES AND METHOD FOR PRODUCING THEM. (57) 1. Derivatives of the pyridazino- (3,4-b) -indole of the general formula —J ^ N ~ Ar cn ₃ where Ar is phenyl or p-tolyl. 2. A method of producing compounds pop. 1, characterized in that the ethyl ester of 1-methyl-3-arylazoindolyl-2-acetic acid of the general formula cn ₂ coox ₂ n ₅ , cn ₃ where Ar has the above meanings, is subjected to cyclization with caustic alkali in an alcoholic medium at boiling.