Synthesis of a series of vicinal diamines with potential biological activity

Kurteva, Vanya; Lyapova, Maria J.

doi:10.2478/bf02482731

Cited by 5 publications

(4 citation statements)

References 19 publications

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“…13 Very recently, the method has been applied to the synthesis of a variety of enantiomerically pure azetidines with yields ranging from 44 to 80%. 13b Only one example of a cyclic sulfate is recorded, 14 as well as diphenylsulfonium 15 and azide 16 as leaving groups.…”

Section: Halides Sulfonic Esters Triflates Etc Leaving Groupsmentioning

confidence: 99%

“…Up to now, the scope of the reaction has been investigated by the synthesis of a series of variously substituted monoand polycyclic azetidinone derivatives (Table 8). Examples of cis-and trans-3,4-disubstituted β-lactams were stereospecifically produced from the corresponding SPIXs (Table 8, entries 4-7), and enantiopure 3,4-cis-fused derivated were formed starting from amino acids such as alanine, valine, tryptophan, and proline, through an intramolecolar nitrone cycloaddition followed by the acid-induced ring contraction (Table 8, entries [16][17][18][19].…”

Section: Isoxazoles and Related Compoundsmentioning

confidence: 99%

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Novel Syntheses of Azetidines and Azetidinones

2008

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Primary amines reacted upon 4,6-ditosylates of glucopyranosides 47 to give compounds 48a,c, with an azetidine ring formed between C4 and C6 of the pyranose ring, in good yields. Interestingly, corresponding mannopyranosides led to the uncyclized 4,6-diamino-4,6-dideoxy compounds (Scheme 13). 11f An azetidine isostere 52 of the oxetane-type taxane 1-deoxy-2-debenzoyloxy-4-deacetylbaccatin VI was synthesized starting from the alkaloid 2′-deacetoxyaustrospicatine 49 (Scheme 14). 10i Scheme

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Section: Halides Sulfonic Esters Triflates Etc Leaving Groupsmentioning

confidence: 99%

Section: Isoxazoles and Related Compoundsmentioning

confidence: 99%

Novel Syntheses of Azetidines and Azetidinones

2008

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“…Furthermore, they are used in laboratory and industry as reagents and synthetic products of medical and pharmaceutical interest [3][4][5][6].…”

Section: Introductionmentioning

confidence: 99%

Conformational study of charged cyclohexyldiamines and their gas phase acid–base properties

Jesus

Redinha

2011

Struct Chem

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Quantum chemical calculations employing the MP2/aug-cc-pVDZ model chemistry have been used to investigate the structure of mono-and diprotonated forms of cyclohexyldiamine (CHDA) isomers. The strength of the intramolecular hydrogen bonds and ion-dipole interactions between the amino groups, which play a key role in the conformational behaviour of the monoprotonated forms, is estimated by isodesmic reactions and electrostatic calculations. The energy variations found for the diprotonated forms are explained by the electrostatic repulsions between the amino groups. From the Gibbs energies and enthalpies calculated for the neutral and protonated CHDAs, the gasphase basicities and proton affinities of the neutral and monoprotonated forms were determined and discussed.

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“…The multistep synthesis of the optically active imidazole-2-thiones occurs with preservation of the stereochemistry. In addition, many derivatives of chiral 1,2-diamines [13,15,31,32], imidazolium salts [33,34,35] as well as numerous imidazole-2-thiones [36,37] display diverse biological activities. Nevertheless, their alkoxy derivatives are practically unknown.…”

Section: Discussionmentioning

confidence: 99%

2-Unsubstituted Imidazole N-Oxides as Novel Precursors of Chiral 3-Alkoxyimidazol-2-ylidenes Derived from trans-1,2-Diaminocyclohexane and Other Chiral Amino Compounds

et al. 2019

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‘Desymmetrization’ of trans-1,2-diaminocyclohexane by treatment with α,ω-dihalogenated alkylation reagents leads to mono-NH2 derivatives (‘primary-tertiary diamines’). Upon reaction with formaldehyde, these products formed monomeric formaldimines. Subsequently, reactions of the formaldimines with α-hydroxyiminoketones led to the corresponding 2-unsubstituted imidazole N-oxide derivatives, which were used here as new substrates for the in situ generation of chiral imidazol-2-ylidenes. Upon O-selective benzylation, new chiral imidazolium salts were obtained, which were deprotonated by treatment with triethylamine in the presence of elemental sulfur. Under these conditions, the intermediate imidazol-2-ylidenes were trapped by elemental sulfur, yielding the corresponding chiral non-enolizable imidazole-2-thiones in good yields. Analogous reaction sequences, starting with imidazole N-oxides derived from enantiopure primary amines, amino alcohols, and amino acids, leading to the corresponding 3-alkoxyimidazole-2-thiones were also studied.

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Synthesis of a series of vicinal diamines with potential biological activity

Cited by 5 publications

References 19 publications

Novel Syntheses of Azetidines and Azetidinones

Novel Syntheses of Azetidines and Azetidinones

Conformational study of charged cyclohexyldiamines and their gas phase acid–base properties

2-Unsubstituted Imidazole N-Oxides as Novel Precursors of Chiral 3-Alkoxyimidazol-2-ylidenes Derived from trans-1,2-Diaminocyclohexane and Other Chiral Amino Compounds

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