This minireview presents the synthesis and applications of enaminones, enaminoesters, and related compounds. A metal‐free synthesis of pyridines and fused pyridines, pyridyl‐substituted amino acids, ...hydroxy acids, and polyols which is enabled by ring switching methodology is described, as well as a simple metal‐free synthesis of aryl‐substituted pyridines, and polysubstituted pyridines from polysubstituted butadiene.
A simple metal‐free synthesis of aryl‐substituted pyridines, and the synthesis of polysubstituted pyridines from enaminones, enaminoesters, amino acids, and polysubstituted butadienes is described.
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2.
Professor Miha Tišler Branko Stanovnik
Acta chimica Slovenica,
12/2017, Volume:
64, Issue:
4
Journal Article
Open access
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For more than a century, 1,3-dicarbonyl compounds and their derivatives have been some of the most versatile and frequently employed C3 synthons in organic, especially heterocyclic, synthesis. They ...are starting materials or key intermediates in the preparation of furans, pyrans, pyrroles, pyrazoles, pryidines, pyrimidines, and their fused analogues.
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A general four-step transformation of alkyl, cycloalkyl, aryl, and heteroaryl methyl ketones via 3-(dimethylamino)-1-substituted-prop-2-en-1-ones, followed by microwave 2+2 cycloaddition of dimethyl ...acetylenedicarboxylate, cyclization of (2E,3E)-2-(dimethylamino)methylene-3-(2-substituted)succinates with ammonia or hydroxylamine hydrochloride into 2-substituted-pyridine-4,5-dicarboxylates and their N-oxides and final cyclization with hydrazine hydrate into of 7-substituted-2,3-dihydropyrido3,4-dpyridazine-1,4-diones and 1,4-dioxo-7-substituted-1,2,3,4-tetrahydropyrido4,3-dpyridazine 6-oxides is shown.
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The reaction of ortho-lithiated aryloxiranes with various enaminones straightforwardly affords new functionalized isochromanes as mixtures of two epimeric stereoisomers in reasonable to very good ...yields (50–90%). The two diastereomers, which show a high structural variability, can be easily separated by column chromatography.
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The synthesis of U-shaped conformationally constrained analogues of peptides based on the 3-amino-2-oxo-1,5-diazabicyclo3.3.0octane-8-carboxylic acid scaffold was developed. 3+2 Cycloadditions of ...(1Z,4R*,5R*)-1-arylmethylidene-4-benzyloxycarbonylamino-3-oxo-5-phenylpyrazolidin-1-ium-2-ides to tert-butyl acrylate and tert-butyl methacrylate gave the corresponding racemic cycloadducts, in most cases as mixtures of isomers, which were separated by preparative chromatography. Selective deprotection of the C- and the N-terminal of these heterocyclic dipeptides followed by coupling with (S)-alanine derivatives and chromatographic separation furnished the non-racemic tripeptides as target compounds. The structures of racemic cycloadducts and non-racemic final products were determined by NMR spectroscopy and X-ray diffraction. The synthesized compounds were also evaluated for inhibition of MurD ligase and d-alanine:d-alanine ligase.
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Regioselective copper(i) iodide-catalyzed cycloadditions of chiral pyrazolidin-3-on-1-azomethine imines 3a-j to ethyl propiolate 4 gave cycloadducts 5a-h and 5'i and 5/5'j as single regioisomers. In ...terms of facial selectivity, cycloadducts 5a-h and 5'i were obtained as single diastereomers, whereas the reaction of dipole 3j was less selective and gave a mixture of 5j and 5'j in a ratio of 15:85. Stereoselectivity of copper(i) iodide-catalyzed cycloadditions of ethyl propiolate 4 to azomethine imines 3 was controlled by the stereodirecting phenyl group at position 5 and by the ortho-substituents at the 1'-Ar residue.
A library of 15 1,6,7,9-tetrasubstituted 6,7,9,9a-tetrahydro-5
H-pyrazolo1,2-
apyrrolo3,4-
cpyrazole-1,3,5(2
H,3a
H)-triones was prepared by combinatorial stereoselective cycloadditions of (1
Z,4
R
...∗,5
R
∗)-1-arylmethylidene-4-benzoylamino-5-phenylpyrazolidin-3-on-1-azomethine imines to
N-substituted maleimides. Stereochemistry was controlled by the stereodirecting phenyl group at position-3 and by the
ortho-substituents at the aromatic ring at position-1′ in azomethine imines. Consequently, two sets of diastereomeric cycloadducts were obtained, one set from the
ortho-unsubstituted dipoles and the other set from the
ortho-disubstituted dipoles.
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