Search results for "cyclization"
showing 10 items of 114 documents
Tandem Reactions of 1,2,4-Oxadiazoles with Allylamines
2011
A reaction of 3-chloro-1,2,4-oxadiazoles with allylamine and diallylamine has been investigated. 3,3a,4,5-Tetrahydroisoxazolo[3,4-d]pyrimidines are produced through a tandem ANRORC/[3 + 2]cycloaddition pathway consisting of the addition of allylamine to the 1,2,4-oxadiazole, followed by ring opening, nitrone formation, and finally cycloaddition. 3-N-Allylamino-1,2,4-oxadiazoles were also obtained as minor products through a classical SNAr. Conversely, a reaction with diallylamine produces 3-N,N-diallylamino-1,2,4-oxadiazole and imidazoline through tandem SNAr/aziridination and nucleophilic ring opening.
A quantitative study of substituent effects on oxidative cyclization of some 2-aryl-substituted aldehyde thiosemicarbazones induced by ferric chlorid…
1999
As a development of our previous work, we performed a kinetic study of the oxidative cyclization reaction of some 2,4-diaryl-substituted aldehyde thiosemicarbazones 1a-n induced by ferric chloride and by cupric perchlorate. The results of cyclization of 1a-n were compared to those of the corresponding 2-methyl derivatives. The kinetic data were analyzed by means of the Hammett's equation.
Oxidative cyclization of some aldehyde semicarbazones induced by metallic salts
1993
The oxidative cyclization of some aldehyde semicarbazones 10 with four different oxidizing agents has been effected. The structure of the semicarbazones and the nature of cyclizing agent affected the rate and yield of cyclization but they did not show any influence on the regiochemistry of reaction. In fact, 1,2,4-triazoline 20 was the only heterocyclic ring obtained by the cyclization reaction.
ChemInform Abstract: Oxidative Cyclization of Some Aldehyde Semicarbazones Induced by Metallic Salts.
2010
The oxidative cyclization of some aldehyde semicarbazones 10 with four different oxidizing agents has been effected. The structure of the semicarbazones and the nature of cyclizing agent affected the rate and yield of cyclization but they did not show any influence on the regiochemistry of reaction. In fact, 1,2,4-triazoline 20 was the only heterocyclic ring obtained by the cyclization reaction.
Asymmetric synthesis of fluorinated cyclic beta-amino acid derivatives through cross metathesis.
2006
The asymmetric synthesis of several fluorinated cis-2-aminocycloalkane carboxylic acids (cis-2-ACACs) with a cross metathesis (CM) reaction as the key step has been carried out, constituting the first time a metathesis protocol has been undertaken with fluorinated imidoyl chlorides. Subsequent chemoselective hydrogenation of the olefin moiety, Dieckmann condensation, and stereoselective reduction of the iminic double bond afforded the corresponding beta-amino esters with several ring sizes. The asymmetric version of the process was achieved by using (-)-8-phenylmenthol as a chiral auxiliary.
Oxidative cyclization of aldehyde thiosemicarbazones induced by potassium ferricyanide and by tris(p-bromophenyl)amino hexachloroantimoniate. A joint…
2005
The oxidative ring closure reaction of some aryl-substituted thiosemicarbazones induced by "bona fide" one-electron abstracting agents was investigated, by means of both experimental and computational techniques. The corresponding 1,2,4-triazole derivatives were the only cyclization products observed. The occurrence of two slightly different mechanistic pathways for the reaction is discussed.
Mo-Based Oxidizers as Powerful Tools for the Synthesis of Thia- and Selenaheterocycles.
2019
A highly efficient synthetic protocol for the synthesis of thia- and selenaheterocycles has been developed. By employing a MoCl5 -mediated intramolecular dehydrogenative coupling reaction, a broad variety of structural motifs was isolated in yields up to 94 %. The electrophilic key transformation is tolerated by several labile moieties like halides and tertiary alkyl groups. Due to the use of disulfide or diselenide precursors, a high atom efficiency was achieved.
Synthesis of 4-amino-5-fluoropyrimidines and 5-amino-4-fluoropyrazoles from a β-fluoroenolate salt
2020
A synthesis of fluorinated pyrimidines under mild conditions from amidine hydrochlorides and the recently described potassium 2-cyano-2-fluoroethenolate was developed. A broad substrate scope was tested and mostly excellent yields were obtained. The synthesis of fluorinated aminopyrazoles from the same fluorinated precursor could be demonstrated but proceeded with lower efficiency.
Base-Dependent Stereodivergent Intramolecular Aza-Michael Reaction: Asymmetric Synthesis of 1,3-Disubstituted Isoindolines
2013
The nucleophilic addition (A(N)) / intramolecular aza-Michael reaction (IMAMR) process on Ellman's tert-butylsulfinyl imines, bearing a Michael acceptor in the ortho position, is studied. This reaction affords 1,3-disubstituted isoindolines with a wide range of substituents in good yields and diastereoselectivities. Interestingly, careful choice of the base for the aza-Michael step allows either the cis or the trans diastereoisomers to be exclusively obtained. This stereodivergent cyclization has enabled the synthesis of C2-symmetric bisacetate-substituted isoindolines. In addition, bisacetate isoindolines bearing two well-differentiated ester moieties are also noteworthy because they may a…
An Insight into Substrate-Dependent Fluorination of some Highly Substituted Alicyclic Scaffolds
2017
The substrate-dependent fluorination of some highly-functionalized cyclopentane derivatives with multiple chiral centers has been investigated. The key steps of the stereocontrolled syntheses are the oxidative cleavage of the ring carbon–carbon double bond of readily available diexo or diendo norbornene β-amino acid derivatives followed by transformation of the resulted dialdehyde stereoisomers by reduction. Finally, substrate-directable chemodifferentiation of different types of hydroxy groups under fluorination procedures gave various densely functionalized alicyclic derivatives or heterocycles.