Uroš Grošelj

Stereoselective synthesis of (1R,3R,4R)-3-(1,2,4-triazolo[4,3-x]azin-3-yl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ones

Abstract (1R,3R,4R)-3-(1,2,4-Triazolo[4,3-x]azin-3-yl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ones were prepared in 68–94% d.e. in three steps from (1R)-(+)-camphor via coupling of (1R,4R)-3-[(E)-(dimethylamino)methylidene]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one with hydrazinoazines followed by oxidative cyclisation of the intermediate hydrazones with methanolic bromine. The structures were determined by 2D NMR techniques and NOESY spectroscopy as well as by X-ray diffraction.

1,3-Dipolar Cycloadditions to (5Z)-1-Acyl-5-(cyanomethylidene)- imidazolidine-2,4-diones: Synthesis and Transformations of Spirohydantoin Derivatives

Cycloadditions of various 1,3-dipoles to (5Z)-1-acyl-5-(cyanomethylidene)-3-methylimidazolidine-2,4-diones 8 or 9, prepared in 3 steps from hydantoin (1) (Schemesu20051 and 2), were studied. In all cases, reactions proceeded regio- and stereoselectively. The type of product depended on the 1,3-dipole and/or dipolarophile employed as well as on reaction conditions. Thus, with stable dipoles under neutral conditions, spirohydantoin derivatives 12u2009–u200916 were obtained (Schemeu20052), while under basic or acidic conditions, pyrazole- or isoxazole-5-carboxamides 18 and 23u2009–u200926 and carboxylate 27 were formed via aromatization of the newly formed dihydroazole ring, followed by the simultaneous cleavage of the hydantoin ring (Schemesu20053u2009–u20095).

Parallel synthesis of 7-heteroaryl-pyrazolo[1,5-a]pyrimidine-3-carboxamides

A simple and practical four-step protocol for the parallel synthesis of 7-heteroaryl-pyrazolo[1,5-

Reactions of Methyl Ketones and (Hetero)arylcarboxamides with N,N-Dimethylacetamide Dimethyl Acetal. A Simple Metal-Free Synthesis of 2,4,6-Trisubstituted Pyridines*

a

Synthesis of 2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-3-((dimethylamino)methyl)camphor organocatalysts

a]pyrimidine-3-carboxamides was developed. The synthesis starts with transformation of commercially available 2-acetylpyridine and acetylpyrazine with

Synthesis and Rotational Isomerism of 1-Substituted Methyl (S)-[5-(2-Nitrophenyl)-1H-pyrazole-4-carbonyl]alaninates

N,