A highly efficient and general -monomethylation of functionalized primary amines via formylation--borane:methyl sulfide reduction

Krishnamurthy, S.

doi:10.1016/s0040-4039(00)87603-0

Cited by 111 publications

(60 citation statements)

References 20 publications

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“…Formylation of the amine with acetic formic anhydride followed by in situ borane-dimethyl sulfide reduction afforded the corresponding N -methylamines 44. The products 15 and 16 obtained in this way were free of any contamination by the dialkylation product.…”

Section: Chemistrymentioning

confidence: 96%

Selective 5-Hydroxytryptamine 2C Receptor Agonists Derived from the Lead Compound Tranylcypromine: Identification of Drugs with Antidepressant-Like Action

et al. 2009

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We report here the design, synthesis, and pharmacological properties of a series of compounds related to tranylcypromine (9), which itself was discovered as a lead compound in a high-throughput screening campaign. Starting from 9, which shows modest activity as a 5-HT 2C agonist, a series of 1-aminomethyl-2-phenylcyclopropanes was investigated as 5-HT 2C agonists through iterative structural modifications. Key pharmacophore feature of this new class of ligands is a 2-aminomethyltrans-cyclopropyl side chain attached to a substituted benzene ring. Among the tested compounds, several were potent and efficacious 5-HT 2C receptor agonists with selectivity over both 5-HT 2A and 5-HT 2B receptors in functional assays. The most promising compound is 37 with 120-and 14-fold selectivity over 5-HT 2A and 5-HT 2B , respectively (EC 50 = 585, 65, and 4.8 nM at the 2A, 2B, and 2C subtypes, respectively). In animal studies, compound 37 (10-60 mg/kg) decreased immobility time in the mouse forced swim test.

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Section: Chemistrymentioning

confidence: 96%

Selective 5-Hydroxytryptamine 2C Receptor Agonists Derived from the Lead Compound Tranylcypromine: Identification of Drugs with Antidepressant-Like Action

et al. 2009

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“…Formylation of aryl amines was carried out by the action of acetic formic anhydride by a modified procedure (Eq. (3)) [9]. The next step in preparing the target ferrocenylbiphenyl ligands was dehydration of the substituted formanilides, which was carried out by the action of diphosgene in the presence of base [10].…”

Section: ð1þmentioning

confidence: 99%

“…The synthetic pathways were developed as a first step toward realizing the goal of preparing metallomesogens based on ferrocenyl-polyphenylenes coordinated to gold(I) thiophenolates, in which long chain alkoxy groups are substituted para to sulfur on the phenyl ring. The crystal structures of (chloro)gold{(4 0 -ferrocenyl[1,1 0 ]biphenyl-4-yl)isocyanide} (9) and 12 are reported. Complex 9 crystallizes in the space group P2 1 /c and 12 crystallizes in P2 1 /n.…”

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confidence: 99%

Synthesis, crystal and molecular structure of gold(I) thiophenolate with 4′-ferrocenyl[1,1′]biphenylisocyanides

Dyadchenko

Belov

Lemenovskii

et al. 2010

Journal of Organometallic Chemistry

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“…No entanto, amidas terciárias sofrem reduções por boranos em condições mais brandas do que amidas primárias e secundárias 66 . Nas reduções empregando diborano em THF a 0 °C, amidas terciárias são facilmente reduzidas e as amidas primárias são lentamente reduzidas, exibindo 50% de redução após 48 h 67,68 . De um modo geral, verificase que a reatividade diminui na ordem 35,69,70 : terciárias > secundári-as > primárias.…”

Section: (7)unclassified

Redução de amidas por boranos

2002

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Recebido em 27/3/01; aceito em 25/7/01 REDUCTION OF AMIDES BY BORANES. Despite the fact that boranes are frequently used in amide reductions, the reaction mechanisms of the involved are note well known. This work presents the results of a bibliographic search on probable amide reduction mechanisms and an analysis of the existing literature. Steric and electronic effects were considered in light of reactivity since it could be concluded that the formation of intermediates and products depends mainly on the substitution patterns of both the boron and nitrogen atoms. Otherwise, results described in the literature for the reactions of boranes, sodium borohydride, lithium aluminum hydride, alkylboranes or haloboranes with others functional groups such as carboxylic acids, esters, ketones and alkenes were analysed with the aim to obtain something about the N-substituted amide reactions employing boranes.Keywords: amides; reactivity of boranes; reduction. INTRODUÇÃOAmidas estão envolvidas em vários processos químicos e bioló-gicos e têm sido empregadas em diversas classes de medicamentos como hipnóticos (zolpidem, zopiclone e acecarbromal), anticonvulsantes (carbamazepina, felbamato e progabida), tranqüilizan-tes (metilprilona e glutetimida), relaxantes musculares (alildietilacetamida, valnoctamida e oxanamida) e antivirais (AZT e ribavirin) 1-3 . Além disto, as amidas são empregadas também na síntese de agentes radiofarmacêuticos em medicina nuclear 4 .De um modo geral, as propriedades químicas e biológicas das amidas estão relacionadas com a ordem da ligação carbono-nitrogê-nio, a qual expressa a deslocalização eletrônica entre os heteroátomos, sendo influenciada por fatores estéricos e eletrônicos dos grupos substituintes presentes tanto no nitrogênio quanto no carbono carbonílico. Devido à deslocalização eletrônica, essa ligação (denominada também de ligação peptídica) apresenta um alto grau de rigidez, com barreiras de energia rotacional variando entre 50 e 100 kJ/mol 5,6 . A rigidez da ligação carbono-nitrogênio proporciona uma planaridade ao grupo amido em peptídeos e proteínas, a qual, somada aos efeitos de ligações de hidrogênio intramoleculares, determina formas estruturais helicoidais (Figura 1).Nos processos químicos, as reduções de amidas têm sido muito empregadas no desenvolvimento de metodologias para formação de aminas, substâncias também importantes quimicamente 8 . Os procedimentos utilizados para reduções de amidas podem ser agrupados em quatro tipos: reações eletroquímicas; reações com metais; reduções nucleofílicas e reduções eletrofílicas.As reações eletroquímicas e aquelas envolvendo metais são dependentes das condições de reação 9,10 , podendo levar à formação competitiva entre aminas, aldeídos ou álcoois [11][12][13][14][15][16][17] . As reduções nucleofílicas, empregando principalmente boro-hidreto de sódio (NaBH 4 ), hidreto de lítio e alumínio (LiAlH 4 ) e seus derivados 18-28 , proporcionam, além de aminas, a formação de outros produtos de reação. Assim, tris-(dialquilamino)-alumino-hidreto...

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A highly efficient and general -monomethylation of functionalized primary amines via formylation--borane:methyl sulfide reduction

Cited by 111 publications

References 20 publications

Selective 5-Hydroxytryptamine 2C Receptor Agonists Derived from the Lead Compound Tranylcypromine: Identification of Drugs with Antidepressant-Like Action

Selective 5-Hydroxytryptamine 2C Receptor Agonists Derived from the Lead Compound Tranylcypromine: Identification of Drugs with Antidepressant-Like Action

Synthesis, crystal and molecular structure of gold(I) thiophenolate with 4′-ferrocenyl[1,1′]biphenylisocyanides

Redução de amidas por boranos

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