Acetals of 4-amino-2-butynal : Application to the synthesis of N6-substituted adenines with an acetylenic side chain, potential cytokinins

Haidoune, M.; Giffard, Michel; Mornet, R.; Gorgues, A.

doi:10.1016/s0040-4039(00)99296-7

Cited by 9 publications

(1 citation statement)

References 5 publications

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“…After extraction with ethyl acetate (200 then 100 mL), the combined organic phases were washed with brine (50 mL), dried with magnesium sulfate, and concentrated in vacuo to provide amine 10 (5.04 g, 32.0 mmol, 91%) as a yellow oil, which was used without further purification. Known compound . ν max /cm -1 3371, 2973, 1129; 1 H NMR (300 MHz, CDCl 3 ) δ 5.24 (s, 1H), 3.70 (dq, J = 9.4, 7.2 Hz, 2H), 3.54 (dq, J = 9.4, 7.2 Hz, 2H), 3.44 (s, 2H), 1.50 (bs, 2H), 1.20 (t, J = 7.2 Hz, 6H); 13 C NMR (75 MHz, CDCl 3 ) δ 91.7, 86.6, 78.1, 61.1, 31.8, 15.4.…”

Section: Methodsmentioning

confidence: 99%

New Approaches to Bicylic Vinyl Heterocycles from Propargylic Acetals

2004

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The paper describes further studies on the intramolecular carbolithiation of propargylic acetals with aryllithiums leading to 2-vinylbenzofurans and 3-vinylfuropyridines. Attempts to extend the cascade to [4.4.0] binuclear heterocycles met with limited success. An alternative, two-step entry to such ring systems has been developed using the palladium-induced cyclization/hydride capture methodology. A new route to isoquinilinones from simple benzamides is also disclosed.

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Section: Methodsmentioning

confidence: 99%

New Approaches to Bicylic Vinyl Heterocycles from Propargylic Acetals

2004

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Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents

2002

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Reductive amination is an important tool for synthetic organic chemists in the construction of carbon‐nitrogen bonds. This reaction, also termed reductive alkylation, involves condensation of an aldehyde or ketone with an amine in the presence of a reducing agent. A wide variety of substrates can be used including aliphatic and aromatic aldehydes and ketones, and even benzophenones. A range of amines from ammonia to aromatic amines, including those with electron‐withdrawing substituents, can be employed. For particularly sluggish reactions, such as those involving weakly electrophilic carbonyl groups, poorly nucleophilic amines, or sterically congested reactive centers, additives such as molecular sieves or Lewis acids are often useful. This chapter focuses on those conditions in which the carbonyl component, amine, and reducing reagent react in the same vessel. This review is restricted to reductive aminations using borohydride and borane reducing agents. This chapter concentrates on reductive amination chemistry mediated by borohydride and other boron‐containing reducing agents from 1971, the year when sodium cyanoborohydride was introduced, through the middle of 1999. In addition to reductive aminations of aldehyde and ketone substrates, reactions of related structures including acetals, aminals, ketals, carboxylic acids, nitriles, and dicarbonyls that form a nitrogen‐containing ring are reviewed. Intramolecular processes in which the substrate contains both the carbonyl and amine moieties are described. The intramolecular variant is a useful method for preparing cyclic amines. All of the various boron‐containing hydride sources in reductive aminations, including labeled metal hydrides, are reviewed. Instances of reductive aminations that failed are described. Applications of this method to a solid support in parallel synthesis in combinatorial chemistry as well as reductive aminations that proceed in tandem with a second reaction such as reductive lactamizations are discussed.

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Preparation of Alcohols

1992

Compendium of Organic Synthetic Methods

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Acetals of 4-amino-2-butynal : Application to the synthesis of N6-substituted adenines with an acetylenic side chain, potential cytokinins

Cited by 9 publications

References 5 publications

New Approaches to Bicylic Vinyl Heterocycles from Propargylic Acetals

New Approaches to Bicylic Vinyl Heterocycles from Propargylic Acetals

Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents

Preparation of Alcohols

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