Structures of nitramine and isonitramine — Alkaloids of a new type from plants of the genusNitraria

Ибрагимов, А. А.; Osmanov, Z.; Ташходжаев, Б.; Абдуллаев, Н. Д.; Yagudaev, M. R.; Yunusov, S. Yu.

doi:10.1007/bf00565164

Cited by 15 publications

(11 citation statements)

References 2 publications

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“…The AM1 method gave results agreeing well with those obtained previously by experiment [1]. They showed that, for the molecules of both alkaloids, conformations with intraHBs of the N--H---O type ( (1) and (4)) are preferential.…”

supporting

confidence: 89%

“…The covalent N--H bond participating in the formation of the hydrogen bond (conformations (1) and (4)) is lengthened by an average of 0.004 ,~ (the length of the N--H bond is 1.004 .~ for (3) and (6) and 1.008 for (1) and (4)), while the analogous O--H bond is lengthened by only 0.001 .~ (the length of the O--H bond is 0.964/~ for (1), (3), (4) and (6), and 0.965 ~, for substances (2) and (5)). The O..-H hydrogen bond ( (1) and (4)) is shorter by -0.120, on average, than the N...H hydrogen bond, which is due to the smaller distance between the heteroatoms in the preferential conformations (1) and (4) (-2.9 ]k) than in conformations (2) and (5) (-3.07 A). In the conformations without intraHBs ((3) and (6)) the distance between the heteroatoms averages 4.15 A.…”

mentioning

confidence: 95%

“…However, in the liquid phase the free bases exist preferentially in conformations with intraHBs ( (1) and (4), or (2) and (5)), as is shown by a shift of the absorption band of active hydrogen in IR spectra into the 3200-3235 cm -1 region, which is retained on dilution [1].…”

mentioning

confidence: 95%

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Quantum-chemical study of the spiropiperidine alkaloids ofNitraria I. Intramolecular hydrogen bonds and chemical properties of nitramine and isonitramine

Ashirmatova

Ибрагимов²

1996

Chem Nat Compd

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supporting

confidence: 89%

mentioning

confidence: 95%

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Quantum-chemical study of the spiropiperidine alkaloids ofNitraria I. Intramolecular hydrogen bonds and chemical properties of nitramine and isonitramine

Ashirmatova

Ибрагимов²

1996

Chem Nat Compd

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“…We imagined that successful exploration of this inverted strategy would enable rapid, stereocontrolled total syntheses of (−)-isonitramine and (+)-sibirinine. 10 − 12 …”

mentioning

confidence: 99%

Enantioselective Synthesis of α-Quaternary Mannich Adducts by Palladium-Catalyzed Allylic Alkylation: Total Synthesis of (+)-Sibirinine

et al. 2015

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A catalytic enantioselective method for the synthesis of α-quaternary Mannich-type products is reported. The two-step sequence of (1) Mannich reaction followed by (2) decarboxylative enantioselective allylic alkylation serves as a novel strategy to in effect access asymmetric Mannich-type products of “thermodynamic” enolates of substrates possessing additional enolizable positions and acidic protons. Palladium-catalyzed decarboxylative allylic alkylation enables the enantioselective synthesis of five-, six-, and seven-membered ketone, lactam, and other heterocyclic systems. The mild reaction conditions are notable given the acidic free N–H groups and high functional group tolerance in each of the substrates. The utility of this method is highlighted in the first total synthesis of (+)-sibirinine.

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“…The qualitative compositions of the bases in the individual organs are being studied. At the present time, the epigeal part of N. sibirica has yielded isonitramine, nitramine [5], nitraramine…”

Section: Udc 547944/945mentioning

confidence: 99%

Dynamics of the accumulation of the alkaloids ofNitraria sibirica

Osmanov¹,

Ибрагимов²,

Yunusov³

et al. 1982

Chem Nat Compd

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We have studied the total alkaloids present in various organs of Nitr~ga sibirica Pall. as functions of the vegetation period. Attempts were first made to determine the optimum method of extraction, as previously for N. komarovii [i]: the same amounts of samples of the comminuted plant were extracted in parallel by three methods: i) with a 2% solution of acetic acid in chloroform; 2) with methanol; and 3) with chloroform after the plant had been wetted with an 8% solution of ammonia.The purest combined material and the best yield of it were obtained by the use of the third method, which is that generally adopted for the isolation of mixtures of bases, and we subsequently used only this method.The amounts of alkaloids in the buds, flowers, leaves, stems, seeds, fruit, and roots of plants collected in the environs of the village of Rybach'e (KirgSSR) were as follows:

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Structures of nitramine and isonitramine — Alkaloids of a new type from plants of the genusNitraria

Cited by 15 publications

References 2 publications

Quantum-chemical study of the spiropiperidine alkaloids ofNitraria I. Intramolecular hydrogen bonds and chemical properties of nitramine and isonitramine

Quantum-chemical study of the spiropiperidine alkaloids ofNitraria I. Intramolecular hydrogen bonds and chemical properties of nitramine and isonitramine

Enantioselective Synthesis of α-Quaternary Mannich Adducts by Palladium-Catalyzed Allylic Alkylation: Total Synthesis of (+)-Sibirinine

Dynamics of the accumulation of the alkaloids ofNitraria sibirica

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