Halochrome Molekeln 8. Mitteilung. Synthese und acidobasisches Verhalten von 3′‐substituierten 6,11‐Dihydrospiro[[1]benzopyrano[4,3‐<i>b</i>]indol‐6,9′−9′<i>H</i>‐xanthenen]

Gunzenhauser, Sigmund; Balli, Heinz

doi:10.1002/hlca.19890720603

Cited by 9 publications

(3 citation statements)

References 11 publications

(4 reference statements)

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“…When the reaction was conducted using conditions described for a similar reaction (with 15 mole equivalents of benzaldehyde and 30 of sodium cyanoborohydride [19]) NMR analysis of the crude product suggested a small amount of dialkylation had occurred. When the quantity of reagent was decreased (to 2 mole equivalents of benzaldehyde and 3 of sodium cyanoborohydride) only the desired 7-benzylamino-1-isoquinolinamine was formed.…”

Section: Resultsmentioning

confidence: 99%

“…Removal of the solvent by evaporation under reduced pressure gave 1,7-isoquinolinediamine (3) [19]. Compound (3) was dissolved in acetic acid (1.65 mL), the requisite benzaldehyde was added, and the reaction was allowed to stir at room temperature for 30 min.…”

Section: -Nitro-1-isoquinolinamine (9)mentioning

confidence: 99%

“…Though not described in detail, the synthesis of a potential precursor to these compounds, 1,7-isoquinolinediamine (3), has been outlined in the patent literature [17,18]. This study proposes a selective reductive amination of the 7-amino group of 1,7-isoquinolinediamine (3) to provide the target molecules [19]. Using benzaldehyde in this reaction, 7-benzylamino-1-isoquinolinamine (2a) would be the expected product.…”

Section: Introductionmentioning

confidence: 97%

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Synthesis and antimalarial activity of 7‐benzylamino‐1‐isoquinolinamines

Gutteridge¹,

Hoffman²,

Bhattacharjee³

et al. 2007

Journal of Heterocyclic Chem

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Computer modelling suggests that 7-benzylamino-1-isoquinolinamines should mediate antimalarial effects by a mechanism distinct from that employed by existing antimalarial drugs. A series of these compounds was prepared in seven synthetic steps, via reductive amination of 1,7-isoquinolinediamine. In vitro efficacy testing of the novel compounds against Plasmodium falciparum revealed them to be potent antimalarial agents.

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Section: Resultsmentioning

confidence: 99%

Section: -Nitro-1-isoquinolinamine (9)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

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Synthesis and antimalarial activity of 7‐benzylamino‐1‐isoquinolinamines

Gutteridge¹,

Hoffman²,

Bhattacharjee³

et al. 2007

Journal of Heterocyclic Chem

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Sodium Triacetoxyborohydride

Gribble

Abdel‐Magid

2007

Encyclopedia of Reagents for Organic Synthesis

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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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Halochrome Molekeln 8. Mitteilung. Synthese und acidobasisches Verhalten von 3′‐substituierten 6,11‐Dihydrospiro[[1]benzopyrano[4,3‐b]indol‐6,9′−9′H‐xanthenen]

Cited by 9 publications

References 11 publications

Synthesis and antimalarial activity of 7‐benzylamino‐1‐isoquinolinamines

Synthesis and antimalarial activity of 7‐benzylamino‐1‐isoquinolinamines

Sodium Triacetoxyborohydride

Reductive Aminations of Carbonyl Compounds with Borohydride and Borane Reducing Agents

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