Chemistry of Heterocyclic Compounds最新文献

A method for the synthesis of spiro-1,3,4-thiadiazolines by the reaction of cyclic ketones with oxamic acid thiohydrazides was developed. A number of new nonsteroidal spiro-1,3,4-thiadiazolines was obtained in high yields.

The reaction of acetyl-containing furan-3-carboxylates with substituted hydrazines in an alcohol solution leads to the formation of substituted furan-3-carboxylate hydrazones. The resulting hydrazones have E-configuration, as determined by NMR spectroscopy and X-ray diffraction analysis.

Two groups of isomeric imidazothiazolo[1,2,4]triazines and their oxindolylidene derivatives were obtained from 1-alkyl-3-aryl-4,5-dihydroxyimidazolidin-2-(thi)ones. One of the synthesized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine derivatives showed high cytostatic activity at a concentration of 10 μmol/l against four lines of tumor cells: HL-60(TB) (leukemia, –16.1% growth rate), SF-539 (CNS cancer, –2.6% growth rate), MDA-MB-435 (melanoma, –21.2% growth rate), and RXF 393 (kidney cancer, –6.1 % growth rate).

A method for the synthesis of 2-arylquinazolines is described which involves Chan–Evans–Lam coupling of 2-formylphenylboronic acids with amidines. The reaction is performed at mild conditions compatible with the range of functional groups and is cost-efficient, provided by usage of inexpensive catalyst and reagents. The synthesis method of 2-arylquinazolines presented is of with scope in both 2-formylphenylboronic acids and amidines.

A simple and efficient arylamination reaction of 5-nitroisoquinoline based on the oxidative nucleophilic substitution of hydrogen was demonstrated under metal-catalyst-free conditions. This reaction can be used as a method for the synthesis of isoquinoline-based diarylamines containing a nitroso group in the ortho position, which are compounds with high synthetic potential. The oxidation of the latter leads to the formation of 6-arylamino-5-nitroisoquinoline N-oxides. The absence of the need to introduce leaving groups and a good overall yield are features of this reaction.

When benzannulated dihydroindenochromene and dihydroxanthene derivatives were treated with m-chloroperoxybenzoic acid, oxidative cleavage of the pyran C=C bond and the formation of condensed ketolactones, the derivatives of oxonine-2,6-dione and oxecine-2,7-dione, took place. The reaction proceeded via epoxidation of the pyran double bond followed by the opening of the epoxide and Grob–Wharton fragmentation.

The most recent synthetic methods to produce chromeno[2,3-d]pyrimidine derivatives from 2015 onwards are outlined, and this mini-review is divided into different chapters according to the type of the reaction.

A reaction of 2-trifluoroacetyl-1H-benzo[f]chromenes with N-arylamides of cyanoacetic acid led to the synthesis of a series of 2-oxo-6-trifluoromethylpyridine-3-carboxamides as products of a cascade of the carbo-Michael reaction, Thorpe–Ziegler cyclization, and Dimroth rearrangement. In the case of 1H-benzo[f]chromene-2-carbaldehydes, the corresponding Knoevenagel adducts were isolated.

A new method for the synthesis of previously unknown ethyl 2-amino-1-(aryl)-5-(arylcarbamoyl)-6-oxo-1,6-dihydropyridine-3-carboxylates by a reaction of ethyl 2-cyano-3-ethoxyacrylate with N¹,N³-diarylmalonamides was developed. The antibacterial activity of some of the synthesized compounds was assayed.

An effective method for the synthesis of heterocyclic steroids with the [1,2,5]oxadiazolo[3,4-b]pyrazine and [1,2,5]thiadiazolo[3,4-b]-pyrazine fragments was developed. The structure of the products was confirmed by X-ray structural analysis. The resulting compounds showed high antiproliferative activity against breast (MCF7) and prostate (22Rv1) cancer cells, which was not inferior to that of cisplatin and abiraterone acetate.