Trifluoroacetimidoyl Chlorides Research Articles

ChemInform Abstract: Synthesis of Trifluoromethyltetrazoles via Building Block Strategy.

Abstract A series of 1-substituted-5-trifluoromethyltetrazoles was conveniently prepared from N -substituted trifluoroacetimidoyl chlorides via nucleophilic replacement with azide anion followed by subsequent cyclization in moderate to excellent yield by building block strategy.

Copper-Catalyzed Tandem C-N Bond Formation Reaction: Selective Synthesis of 2-(Trifluoromethyl)benzimidazoles

A highly practical method for the synthesis of fluorinated benzimidazoles was developed by CuI/TMEDA-catalyzed cross-coupling reaction of N-(2-haloaryl)trifluoroacetimidoyl chlorides with primary amines. The present double amination process tolerates the presence of Cl, Br, or I substituent at the 2-position of the phenyl group.

Synthesis of 2-fluoroalkylbenzimidazoles via copper(i)-catalyzed tandem reactions

Preparation of 2-fluoroalkylbenzimidazoles from N-aryl trifluoroacetimidoyl (or bromodifluoroacetimidoyl) chlorides and primary amines has been achieved via copper(I)-catalyzed tandem reactions.

Synthesis of 1,3-Oxathiolan-5-ones and Benzoxathian-4-ones

An efficient synthesis of oxathiol­anone and benzoxathianone derivatives from the reaction of readily available trifluoroacetimidoyl chlorides with mercaptocarboxylic acids is reported. The ring size is critical for this reaction. Thus, although oxathiolanones are readily formed from α -mercaptocarboxylic acids and imidoyl chlorides, application of β-mercaptopropionic acids for this reaction leads to the formation of acyclic rather than cyclic products. However, use of thiosalicylic acid leads to the formation of the benzoxathia­nones, suggesting the requirement of a cis SH and OH arrangement for successful cyclization. The interesting part of this facile transformation is that the imine acts as a 1,1-electrophile without the nitrogen atom being integrated into the hetero­cyclic ring. The scope of the reaction requires exploration.

2,3-Migration in Rh(II)-Catalyzed Reactions of β-Trifluoroacetamido α-Diazocarbonyl Compounds

[Structure: see text] The hydroxy group was directly converted into the trifluoroacetamido group by reacting beta-hydroxy-alpha-diazo carbonyl compounds with trifluoroacetimidoyl chloride in the presence of DBU. Rh(II)-catalyzed reactions of these diazo compounds gave 2,3-migration products in high yields.

Mg‐Promoted Double Silylation of Trifluoroacetimidoyl Chlorides. A New Entry to the Fluorinated Dianion Equivalents.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Mg-promoted double silylation of trifluoroacetimidoyl chlorides. A new entry to the fluorinated dianion equivalents.

[reaction: see text] A Mg(0)/Me(3)SiCl system was found to be effective for the preparation of a novel fluorinated dianion equivalent. A one-pot reaction sequence involving reductive C-F and C-Cl bond cleavage reactions of trifluoroacetimidoyl chlorides afforded bis-silylated difluoroenamines. Subsequent carbon-carbon bond-forming reactions of the bis(silyl)enamines with two kinds of electrophiles gave a variety of difluorinated imines.

N‐(Arylsulfonyl)trihaloacetimidoyl Chlorides and Their Reactions with Phosphites

AbstractWe have developed a convenient synthetic approach to highly reactive N‐(arylsulfonyl)trichloro‐ and ‐trifluoroacetimidoyl chlorides 2 by reacting the corresponding N‐acylsulfonamides with PCl5. The interaction of the imidoyl chlorides with phosphites proceeds through different pathways depending on the substituents in the reagents, and leads to N‐arylsulfonyl‐N‐trichlorovinylphosphoramidates 4, 1‐arylsulfonylamino‐1‐chlorotrifluoroethylphosphonate 5, C,N‐bis(phosphorylated) N‐dihalovinylsulfonamides 8 and α‐(arylsulfonylamino)trifluoroethylidenebis(phosphonates) 10. A rare example of an aza‐Perkow reaction involving a trifluoromethyl group was discovered. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

Diastereoselective synthesis of S-tert-butyl-beta-(trifluoromethyl)isocysteine.

Both diastereoisomers of S-tert-butyl-beta-(trifluoromethyl)isocysteine have been synthesized stereoselectively by the sequential reactions of trifluoroacetimidoyl chloride with the lithium enolate of tert-butyl alpha-tert-butylthioacetate, followed by the diastereoselective reduction of the imino group with sodium borohydride in the presence of zinc(II) or di(ethylene glycol) dimethyl ether, and finally by the deprotection of N-aryl and tert-butyl ester groups.

ChemInform Abstract: Rh(I)‐Catalyzed Coupling Cyclization of N‐Aryl Trifluoroacetimidoyl Chlorides with Alkynes: One‐Pot Synthesis of Fluorinated Quinolines.

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Rh(I)-catalyzed coupling cyclization of N-aryl trifluoroacetimidoyl chlorides with alkynes: one-pot synthesis of fluorinated quinolines.

[reaction: see text]. Rh(I) complexes were found to catalyze the coupling cyclization of N-aryl trifluoroacetimidoyl chlorides with alkynes to afford 2-trifluoromethylated quinolines in good yields. Various alkynes were applied to this cyclization coupling with regioselectivity.

Glycosyl trifluoroacetimidates. Part 1: Preparation and application as new glycosyl donors

Glycosyl (N-phenyl)trifluoroacetimidates, readily prepared from 1-hydroxyl sugars by treatment with (N-phenyl)trifluoroacetimidoyl chloride in the presence of K2CO3, were demonstrated to be effective glycosyl donors.

Studies on organophosphorus compounds 105: A facile synthesis of dialkyl 6-substituted-4-hydroxy-2-trifluoromethylquinoline-3-phosphonates

For the investigation of biological activities of trifluoromethylated heterocyclic compounds bearing a phosphoryl moiety, a series of N-aryliminophosphonates were obtained by reaction of dialkyl 1-methoxycarbonylmethylphosphonates with trifluoroacetimidoyl chlorides using NaH as a deprotonating agent. The resulting intermediates underwent cyclization on refluxing in toluene to give dialkyl 6-substituted-4-hydroxy-2-trifluoromethylquinoline-3-phos-phonates. © 2000 John Wiley & Sons, Inc. Heteroatom Chem 11:240–243, 2000

Synthesis of trifluoromethyltetrazoles via building block strategy

A series of 1-substituted-5-trifluoromethyltetrazoles was conveniently prepared from N-substituted trifluoroacetimidoyl chlorides via nucleophilic replacement with azide anion followed by subsequent cyclization in moderate to excellent yield by building block strategy.

Design of Ribonuclease Mimics for Sequence Specific Cleavage of RNA

Abstract 1-Substituted-4-diethoxyphosphoryl-5-trifluoromethylimidazoles are prepared regioselectively from diethyl isocyanomethylphosphonate and N-substituted trifluoroacetimidoyl chlorides. The reaction mechanism was discussed.

An Efficient and Regioselective Synthesis of 1-Aryl(Alkyl)-4-Diethoxyphosphoryl-5-Trifluoromethylimidazoles

Abstract 1-Substituted-4-diethoxyphosphoryl-5-trifluoromethylimidazoles are prepared regioselectively from diethyl isocyanomethylphosphonate and N-substituted trifluoroacetimidoyl chlorides. The reaction mechanism was discussed.

Design of Ribonuclease Mimics for Sequence Specific Cleavage of Rna

Abstract 1-Substituted-4-diethoxyphosphoryl-5-trifluoromethylimidazoles are prepared regioselectively from diethyl isocyanomethylphosphonate and N-substituted trifluoroacetimidoyl chlorides. The reaction mechanism was discussed.

Facile synthesis of 1-substituted 5-trifluoromethylimidazole-4-carboxylates

Base-induced cycloaddition of ethyl isocyanoacetates to trifluoroacetimidoyl chlorides gives ethyl 5-trifluoromethylimidazole-4-carboxylates with high regioselectivity.

A new and simple approach to N-substituted trifluoroacetimidoyl aryl ketones

Using 1,3-dimethylimidazolium iodide as a catalyst, the reaction of trifluoroacetimidoyl chloride with an aromatic aldehyde in the presence of sodium hydride gives N-substituted trifluoroacetimidoyl aryl ketones.

STUDIES ON ORGANOPHOSPHORUS COMPOUNDS 95. A NOVEL SYNTHESIS OF 2-TRIFLUOROMETHYL-2-(SUBSTITUTED AMINO)ETHYLPHOSPHONATES

Abstract Reactions of alkyl phosphonates with trifluoroacetimidoyl chlorides using an appropriate base followed by subsequent reduction of the intermediates provides 2-trifluoromethyl-2-(substituted amino)-ethylphosphonates.