Allyl amines as ammonia equivalents in the preparation of anilines and heteroarylamines

Jaime‐Figueroa, Saul; Liu, Yanzhou; Muchowski, Joseph M.; Putman, David

doi:10.1016/s0040-4039(97)10877-2

Cited by 156 publications

(57 citation statements)

References 27 publications

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“…Several masked forms of ammonia have been reported in the literature, for example, allylamine, [2] benzophenone imine, [3] and Zn[NA C H T U N G T R E N N U N G (SiMe 3 ) 2 ]. [4] More recently, Trabanco et al [5] reported the use of fluorous tert-butyl carbamate.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Application of a New Fluorous‐Tagged Ammonia Equivalent

Nielsen

Smith

Begtrup

et al. 2010

Chemistry A European J

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A novel fluorous-tagged ammonia equivalent has been developed. It is based on a nitrogen-oxygen bond, which can be cleaved in a traceless manner by a molybdenum complex or samarium diiodide. The application in the synthesis of ureas, amides, sulfonamides, and carbamates is described. The scope of the fluorous N-O linker is exemplified by the synthesis of itopride, a drug used for the treatment of functional dyspepsia. Itopride was synthesized with the aid of fluorous purification methods and the product was isolated in good overall yield, with high purity.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Application of a New Fluorous‐Tagged Ammonia Equivalent

Nielsen

Smith

Begtrup

et al. 2010

Chemistry A European J

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“…For example, p-aminoacetophenone was obtained in 27-56% yields after heating p-bromoacetophenone with ammonia in aqueous EG Z. Guo et al [21][22][23]. Addition of strong chelating ligands, such as thiophene-2-carboxylic acid (TCA), leucine and catechol (CAT), led to a significant decrease in the yields of the amination reaction because ligation of ethylene glycol on copper could be competitively suppressed (Table 1, entries [18][19][20].…”

Section: Resultsmentioning

confidence: 99%

Hemilabile‐coordinated copper promoted amination of aryl halides with ammonia in aqueous ethylene glycol under atmosphere pressure

Guo¹,

Guo²,

Song³

et al. 2009

Applied Organom Chemis

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Direct amination of aryl iodides and bromides with ammonia under 1 atm pressure has been effected using in situ-generated hemilabile coordinated copper(I) species from copper(I) halides or copper metal in aqueous ethylene glycol, producing primary aromatic amines in good yields. Ammonia pressure and water were found to accelerate the copper-mediated reaction while strong chelating ligands showed a suppression effect. A rationale for the copper-mediated amination of aryl halides with ammonia is given based on a double-face role of chelating effect.

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“…18 This was subjected to a second alkylation using the α-bromoacetylated Evans oxazolidinone 18 19 to give the chiral intermediate 19. Stereoselective (R)-introduction of the carboxymethyl ester using tert-butyl α-bromoacetate and NaHMDS in THF (−78 °C, then room temperature) gave 20, which was hydrolyzed to the desired aza-containing 9.…”

Section: Resultsmentioning

confidence: 99%

Structural Examination of Ring-Closing Metathesis-Derived 15-Member Macrocycles as Grb2 SH2 Domain-Binding Tetrapeptide Mimetics

et al. 2007

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Ring-closing metathesis (RCM) was employed to join carboxy-terminal alkenyl glycine side chains together with vinyl-and allyl-functionality appended to the β-methylene of amino-terminal phosphotyrosyl (pTyr) mimetics. This required the synthesis of a variety of new pTyr mimetics, including a novel aza-containing analogue. Many of the resulting 15-member macrocyclic tetrapeptide mimetics exhibited low nanomolar Grb2 SH2 domain-binding affinities in spite of the fact that differing ring junction stereochemistries and geometries of the RCM-derived double bond were employed. The finding that significant latitude exists in the structural requirements for ring closure, may facilitate the development of therapeutically-relevant macrocyle-based Grb2 SH2 domain-binding antagonists. The synthetic approaches used in this study may also find application to peptide mimetics directed at other biological targets.

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Allyl amines as ammonia equivalents in the preparation of anilines and heteroarylamines

Cited by 156 publications

References 27 publications

Synthesis and Application of a New Fluorous‐Tagged Ammonia Equivalent

Synthesis and Application of a New Fluorous‐Tagged Ammonia Equivalent

Hemilabile‐coordinated copper promoted amination of aryl halides with ammonia in aqueous ethylene glycol under atmosphere pressure

Structural Examination of Ring-Closing Metathesis-Derived 15-Member Macrocycles as Grb2 SH2 Domain-Binding Tetrapeptide Mimetics

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