Preparation of polysubstituted isochromanes by addition of ortho2 lithiated aryloxiranes to enaminones is described
COBISS.SI-ID: 1639215
A simple five-step diversity-oriented combinatorial synthesis starts with two-step preparation of 4-tosyloxy- and 4-chloropyridones (diversification at N(1)). This is folowed by Suzuki–Miyaura 4-arylation (diversification at C(4)), hydrolysis of the ester group, and in amidation (diversification at carboxamide nitrogen). Suitable reaction conditions for Suzuki–Miyaura 4-arylation determined by combinatorial screening.
COBISS.SI-ID: 36122373
The synthesis of a novel type of vinylogous peptides with the vinyl fragment inserted into the peptide C–N bond vas developed. Title compounds were prepared via ynone intermediates that are easily available from Boc-amino acids. Coupling at the ‘C-terminal’ was achieved by 1,4-addition of amino esters, whereas coupling at the ‘N-terminal’ required temporary protection of the acidolytically labile enamino moiety. Thus, cyclisation of the ynone with hydroxylamine, acidolytic removal of the Boc group, acylation of the free amine, and hydrogenolytic deprotection of the enamino moiety in the presence of GlyOMe led to the tripeptides with vinylogous amide as the central building block.
COBISS.SI-ID: 1695535
A simple and practical four-step protocol for the parallel synthesis of 7-heteroaryl-pyrazolo[1,5-a]pyrimidine-3-carboxamides was developed. The synthesis starts with transformation of commercially available 2-acetylpyridine and acetylpyrazine with N,N-dimethylformamide dimethylacetal into the corresponding (E)-3-(dimethylamino)-1-(heteroaryl)prop-2-en-1-ones followed by cyclisation with methyl 5-amino-1H-pyrazole-4-carboxylate to give methyl 7-heteroarylpyrazolo[1,5-a]pyrimidine-3-carboxylates. Hydrolysis of the ester group and subsequent amidation of the so formed carboxylic acids with 12 primary and secondary aliphatic amines furnished a library of 24 title compounds in good overall yields and purity.
COBISS.SI-ID: 1608495