UA115741U - METHOD OF PREPARATION OF 3H-THIAZOLO [4,3b] BENZO [g] HINAZOLINE-1,11-DIONE - Google Patents

Abstract

Method of producing 3H-thiazolo [4,3-b] benzo [g] quinazoline-1,11-dione, which consists in the intramolecular condensation of 3- (2-oxo-thiazolidin-4-ylideneamino) -naphthalene-2-carboxylic acid acetic anhydride medium.

Description

A useful model concerns organic chemistry, namely useful organic compounds such as ЗН-thiazolo|4,3-B|benzo|diquinazoline-1,11-dione, which can be used in pharmacology as a drug and a reagent for organic and combinatorial synthesis biologically active compounds.

The combination of the thiazolidone ring with other heterocyclic fragments is a reasoned approach to the creation of "drug-like" molecules from the point of view of the strategy and logic of modern organic and medicinal chemistry, as it enables versatile modification of the original structure to obtain a series of new polyfunctional derivatives.

Thiazoloquinazolines are an important type of heterocyclic systems, the intensive study of which is due to a wide range of biological activity (1Y. Taking into account these circumstances, the synthesis of new substances among the indicated class of compounds is relevant.

There is a known method of obtaining ZN-thiazolo|4,3-bibenzoic|diquinazolin-1,11-dione (21), which is based on the 4-hour heating of a mixture of 4-thioxo-thiazolidin-2-one and 2-amino-naphthoic acid in a medium of ethanol. The yield of the target product in this case is 30 95. o o 5 (c)

N Z voshchonnovo that A 4 p

MN, Z at 4

Disadvantages of the method are the long boiling time of the starting materials (4 hours), release of environmentally hazardous hydrogen sulfide during the reaction, poor reproducibility of results - the yield of ЗН-thiazolo|4,3-BI|benzo|di)quinazoline11,11-dione is low.

The basis of a useful model is the task of improving the method of obtaining currently difficult-to-access ZN-thiazolo|4,3-biI|benzoi|diquinazoline-1,11-dione of the formula: t (c) - c)

And in

M

The set task is solved by the fact that the method of obtaining / ZN-thiazolo|4,3-

BIbenzo|d)quinazoline-1,11-dione includes intramolecular condensation of 3-(2-oxo-thiazole and dyn-4-ylideneamino)-naphthalene-2-carboxylic acid in an acetic anhydride medium to obtain a compound of the formula: t (c) of in)

Zhu

M

The authors first suggested using 3-(2-oxo-thiazolidine-4-ylideneamino)-naphthalene-

From 2g-carboxylic acid (1) as the starting compound. This substance, when using a mild dehydrating agent, which is usually acetic anhydride in the absence of catalysts, is capable of cyclization with the formation of ZN-thiazolo|4,3-B|benzo|dhinazolin-1,11-dione (2).

The method can be illustrated by the following example.

(c) o o -nnvya 5

J

Yi I

C 2

From 4 (c) 1

The specified approach to the synthesis allows obtaining ZN-thiazolo|4,3-bibenzoi|diquinazolin-1,11-dione - a representative of a little-studied heterocyclic system. The reaction takes place during a 20-minute boiling in an acetic anhydride environment, which leads to a significant reduction in the time required to obtain the specified compound. The yield of the target product in this case is more than 55 95 compared to 30 95 according to the known method of its preparation (21, which is carried out in ethanol during a long (4-hour) boiling.

The proposed method makes it possible to obtain the target product ZN-thiazolo|4,3-BIbenzo|diquinazoline-1,11-dione with a high yield, using cheap and easily available starting reagents and to significantly expand the limits of the reaction, which confirms the expected technical result.

To prove the composition and structure of the synthesized compound, well-known physicochemical methods were used, in particular PMR spectroscopy and elemental analysis. The obtained results indicate the conformity of the synthesized compound with the claimed one.

To understand the proposed useful model, below is an example of the preparation of ZN-thiazolo|4,3-b|benzo|dhinazoline-1,11-dione.

Synthesis of ZN-thiazolo|4,3-bibenzoi|d)quinazoline-1,11-dione. 100 ml of acetic anhydride is added to 0.05 mol of 3-(2-oxo-thiazolidine-4-ylideneamino)-naphthalene-2-carboxylic acid. The resulting mixture is boiled for 20 minutes, then cooled and poured into 80 ml of water.

After decomposition of acetic anhydride, the precipitate is filtered, washed with water, methanol and dried. After crystallization from acetic acid - cream crystals with a grayish tint; exit from t. pl. 242-243 "C is 55 95.

The gross formula is Sti«NaMgO25.

Found, 90: M 10.33; 5 12.08.

Calculated, 90: M 10.44; 5 11.95.

H NMR spectrum (DMSO-av, 400 MHz): H NMR spectrum: 4.45 s (2H, CH), 7.56 t (1H, 92-7.46 Hu, 9-7.54 Hz, Ag), 7.57 d (1H, 9U-7.50 Hz, Ag), 7.68 d (1H, y2-7.99 Hz, Ag), 7.84 t (1H, 9U-7.47 Hz, 9-7.55

Gu, Ag), 8.08 d (1H, 9U-7/44 Hz, Ag), 8.21 d (1H, 9U-8.06 Hz, Ag).

З The proposed method is fundamentally new and allows to obtain ZN-thiazolo|4,3-b|benzo|d)quinazoline-1,11-dione from commercially available starting substances in one stage and within a short time (20 min) with a high yield. which favorably distinguishes it from known methods, confirming the intended technical result.

Sources of information: 1. Zimenkovsky B.S. 4-thiazolidones. Chemistry, physiological action, perspectives. Monograph / B.S.

Zimenkovskyi, R.B. Lesyk - Vinnytsia: New Book, 2004. - 106 p. 2. Varotsp N.A. bupipeziz oi bote Mem YuOegimaymev5 oi Tnia2o!9(4,3-5|- apa Tniago!io(2,3-B diipagoiiope Agspim deg Rpapta?ie /N.A. Saroshp, M.A. Avaveyi! A?i? //Agspim deg Rpapatalie. - 1983-MOoY. 316, Mo5. - R. 394-399.

Claims (1)

FORMULA OF A USEFUL MODEL The method of obtaining ZN-thiazolo|4,3-b|benzo(a)quinazoline-1,11-dione of the general formula: (c) (c) - C and M which consists in the intramolecular condensation of 3-(2-oxo -thiazolidine-4-ylideneamino)-naphthalene-2-carboxylic acids in the medium of acetic anhydride.