Aberrant syntheses in higher plants. 3. Synthesis of 4-methylnicotine and an examination of its possible biosynthesis from 4-methylnicotinic acid in Nicotiana tabacum

Leete, Edward; Leete, Sheila A. S.

doi:10.1021/jo00405a007

Cited by 25 publications

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“…The satellites are not symmetrically arranged about the central singlet peaks, the observed asymmetry (Table II) being due to an approach to an AB spin system, and is in agreement with theory.14 Authentic 5-fluoroanabasine was required for comparison with material which might be isolated from N. glauca, and it was prepared by the route illustrated in Scheme I. 15 Ethyl 5-fluoronicotinate (1) was condensed with N-(trimethylsilyl)-2-piperidone (2) in the presence of lithium diisopropylamide to afford, after removal of the trimethylsilyl group with water, 3-(5-fluoronicotinoyl)-2-piperidone (3). Hydrolysis of this lactam with 48% hydrobromic acid yielded 5-fluoroanabaseine (6), whose hydrochloride was reduced with sodium cyanoborohydride to yield 5-fluoroanabasine.…”

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confidence: 58%

Aberrant syntheses in higher plants. 4. Aberrant biosynthesis of 5-fluoroanabasine from 5-fluoro[5,6-14C,13C2]nicotinic acid, established by means of carbon-13 nuclear magnetic resonance

Leete¹

1979

J. Org. Chem.

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confidence: 58%

Aberrant syntheses in higher plants. 4. Aberrant biosynthesis of 5-fluoroanabasine from 5-fluoro[5,6-14C,13C2]nicotinic acid, established by means of carbon-13 nuclear magnetic resonance

Leete¹

1979

J. Org. Chem.

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“…Synthesis of pyrrole and condensed pyrrole derivatives: Several synthesis of pyrrole derivatives utilizing organic cyano compounds as starting components were reported [60][61][62][63][64][65][66][67][68]. The most interesting results of that are demonstrated in Scheme 13 [68][69][70][71][72][73].…”

Section: Scheme 12mentioning

confidence: 99%

The Chemistry of Alkenyl Nitriles and its Utility in Heterocyclic Synthesis

Elgazwy¹

2013

Organic Chem Current Res

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including purines [7,8], pyrimidines [9], pyrazines [10] (some which are widely employed in the fluorescent dye industry [11]), imidazoles [12], biphenylenes [13], porphyrazines (which have great potential in optical sensor technology) [14] and diimines that are used as catalysts [15]. This review highlights the alkenyl nitrile chemistry with the focus on the utility of heterocyclic compounds. The synthesis and chemistry of the highly strained aryl nitrile is also briefly reviewed [16]. Heterocycles are ubiquitous in all kind of compounds of interest, and among all the possible synthetic methods of achieving their introduction into an structure, probably the use of a alkenyl nitrile analogue is the most direct one. The present review deals with the generation and synthetic uses of alkenyl nitriles and aryl nitriles formed in heterocyclic synthesis, and can be considered as an update of our revision published in 2007 on this topical [17]. Therefore, only references published from the second quarter of 2003 until the third quarter of 2010 are included, and the same restrictions to the literature coverage applied. Thus, only heterocycles compounds which are found applicability are considered. As previously, the present review is organized by the type of ring members and subdivided by the type of heterocycles fused compounds, including methods for their preparation and their synthetic uses. New developments in the utilities of some alkenyl nitriles in heterocyclic synthesis are reviewed. General synthetic routes based on the utilization of alkenyl nitriles of active imines are discussed. The major methods and modifications are analyzed [18-21]. In this review, which covers the literature up to date, we describe the new and improved methods for the construction of the skeletons, with a particular emphasis on the four, five and six membered ring of heterocyclic compounds. Some of these procedures have clear technical advantages over older methods in terms of yield and versatility, but do not employ new chemistry in the construction of the ring systems. The

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“…This strategy has been employed by Leete in a short synthesis of two Nicotiana alkaloids. [119][120][121] (Morpholin-4-yl)-3-pyridylacetonitrile (125) reacted with acrylonitrile and methanolic potassium hydroxide in tertbutanol to furnish dinitrile 126 in 90% yield (Scheme 20). Acid hydrolysis to the ketone and catalytic hydrogenation gave nornicotine (129, 60%) along with myosmine (128, 30%).…”

Section: Scheme 18 Synthesis Of 14-dicarbonyl Compoundsmentioning

confidence: 99%

The Chemistry of Deprotonated α-Aminonitriles

Opatz¹

2009

Synthesis

105

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This review highlights various aspects of the chemistry of the anions of a-aminonitriles. Their structural features and their characteristic reactivity are discussed, along with various methods for their preparation. Special emphasis is given to synthetic applications of deprotonated a-aminonitriles which have been used as valuable and readily accessible synthetic equivalents of acyl anions and a-aminocarbanions.

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Aberrant syntheses in higher plants. 3. Synthesis of 4-methylnicotine and an examination of its possible biosynthesis from 4-methylnicotinic acid in Nicotiana tabacum

Cited by 25 publications

References 2 publications

Aberrant syntheses in higher plants. 4. Aberrant biosynthesis of 5-fluoroanabasine from 5-fluoro[5,6-14C,13C2]nicotinic acid, established by means of carbon-13 nuclear magnetic resonance

Aberrant syntheses in higher plants. 4. Aberrant biosynthesis of 5-fluoroanabasine from 5-fluoro[5,6-14C,13C2]nicotinic acid, established by means of carbon-13 nuclear magnetic resonance

The Chemistry of Alkenyl Nitriles and its Utility in Heterocyclic Synthesis

The Chemistry of Deprotonated α-Aminonitriles

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