Preparation of secondary amines through efficient alkylation of n-substituted trifluoroacetamides

Nordlander, J. Eric; Catalane, David B.; Eberlein, Thomas H.; Farkas, Lee V.; Howe, R.; Stevens, R.; Tripoulas, Nicholas A.; Stansfield, R.; Cox, Jana L.; Payne, Mark J; Viehbeck, A.

doi:10.1016/s0040-4039(01)85789-0

Cited by 35 publications

(14 citation statements)

References 22 publications

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“…Formamide 6 was conveniently obtained by reaction of 5A with formic acid. The N-acylated derivatives (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(22)(23)(24)(25)(26)(27)(28)(29) and the sulfonamide 43 were prepared from 5A (Scheme 1) by treatment with the appropriate acid chloride in the presence of K2CO3 as base and a biphasic medium (according to a variant of the Schotten-Baumann procedure22). In a similar manner, amides 36-38, 41, 42, 44, 45, 49-58, and 60 from the previously described corresponding amines23-27 were obtained.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structure-Activity Relationships of Novel Naphthalenic and Bioisosteric Related Amidic Derivatives as Melatonin Receptor Ligands

Depreux¹,

Lesieur²,

Mansour³

et al. 1994

J. Med. Chem.

148

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A series of N-naphthylethyl amide derivatives were synthesized and evaluated as melatonin receptor ligands. The affinity of each compound for the melatonin receptor was determined by binding studies using [2-125I]iodomelatonin on ovine pars tuberalis membrane homogenates. Structure-activity relationships led to the conclusion that naphthalene is a bioisostere of the indole moiety of melatonin. Moreover it appears that the affinity is strongly affected by the size of the substituent of the nitrogen of the amidic function. Many of these ligands give biphasic dose-response curves which suggests that there may be two melatonin receptor subtypes within the ovine pars tuberalis cells. The replacement of naphthalene by benzofuran or benzothiophene did not strongly alter the affinity for the melatonin receptor. In contrast, the benzimidazole analogue was a poor ligand. Compound 7, the naphthalenic analogue of melatonin, a selective ligand of the melatonin receptor and an agonist derivative, has been selected for clinical development.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Structure-Activity Relationships of Novel Naphthalenic and Bioisosteric Related Amidic Derivatives as Melatonin Receptor Ligands

Depreux¹,

Lesieur²,

Mansour³

et al. 1994

J. Med. Chem.

148

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“…All of the sulphur-containing guanidine compounds are derived from the commonly encountered aminosulphonic acid, taurine (20). Asterbin {21~ found in starfish, is one of the rare acyclic guanidino compounds substituted on two nitrogen atoms.…”

Section: Marine Guanidine Compoundsmentioning

confidence: 99%

“…Asterbin {21~ found in starfish, is one of the rare acyclic guanidino compounds substituted on two nitrogen atoms. (20) …”

Section: Marine Guanidine Compoundsmentioning

confidence: 99%

A general synthesis of the acarnidines

Blunt

Munro

Yorke

1982

Tetrahedron Letters

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“…Among the synthetic strategies, we turned our attention to the Mitsunobu reaction between activated amides and alcohol derivatives. Especially, the trifluoroacetic amide (TFA amide) moiety is known to be very successful in Mitsunobu reactions and is cleaved under mild basic conditions to afford the corresponding amine derivatives. Although Tsunoda et al demonstrated a facile amine synthesis via sequential Mitsunobu reaction of TFA amide derivatives and alcohol derivatives and subsequent TFA cleavage, no attention has been paid to this approach in polymer chemistry, suggesting that polymers featuring TFA amide moieties also can be employed as a facile reactant under Mitsunobu condition and thus providing a new synthetic strategy for polyamine derivatives.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Functional Polyamine Scaffolds via Mitsunobu Post‐Polymerization Modification Reactions

Kakuchi

Théato

2014

Macromol. Rapid Commun.

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A Mitsunobu reaction of trifluoroacetamide (TFA amide) and alcohols is used in a postpolymerization modification process. The reaction is conducted on polystyrene (PSt) bearing 20 mol% TFA amide groups with 4-methyl benzyl alcohol in the presence of a N,N,N′,N ′-tetramethylazodicarboxamide and tributylphosphine as mediators. The Mitsunobu reaction on polymer proceeds efficiently, as confirmed by the obvious precipitation generation during the reaction and the conversion of TFA amide moiety reached 88.6% confirmed by 19 F NMR measurement, yielding PSt bearing tertiary TFA amide moieties. The obtained polymers featuring tertiary TFA amide moieties are deprotected in the presence of tetrabutylammonium hydroxide as a base to afford corresponding polymers featuring functionalized polyamine scaffolds with 92.5% conversion. In addition, the precise structural assignment is proven by synthesis and analysis of the model monomeric compounds and the respective model polymers.

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Preparation of secondary amines through efficient alkylation of n-substituted trifluoroacetamides

Cited by 35 publications

References 22 publications

Synthesis and Structure-Activity Relationships of Novel Naphthalenic and Bioisosteric Related Amidic Derivatives as Melatonin Receptor Ligands

Synthesis and Structure-Activity Relationships of Novel Naphthalenic and Bioisosteric Related Amidic Derivatives as Melatonin Receptor Ligands

A general synthesis of the acarnidines

Preparation of Functional Polyamine Scaffolds via Mitsunobu Post‐Polymerization Modification Reactions

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