Reactions of 1-trichloromethyl-substituted amines with potassium tert-butoxide.

Takamatsu, Masanori; Sekiya, Minoru

doi:10.1248/cpb.28.3098

Cited by 15 publications

(3 citation statements)

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“…[212][213][214][215][216][217] Scheme 34. [236][237][238][239][240][241][242][243] Recently, Wahl et al 244 reported a nucleophilic addition of trimethyl(trichloromethyl)silane (108) to N-phosphinoyl benzaldimines 107 outlining a tetrabutylammonium difluorotriphenylsilicate (TBAT)-catalyzed route to N-phosphinoyl-α-(trichloromethyl)benzylamines 109 in tetrhydrofuran (THF) with good yields within just one hour at room temperature (Scheme 38). The resulting β-hydroxy nitro compounds have been used in various beneficial transformations to provide chiral β -amino alcohols and α-hydroxy carboxylic acids.…”

Section: Addition Reactionsmentioning

confidence: 99%

Design for carbon–carbon bond forming reactions under ambient conditions

Brahmachari

2016

RSC Adv.

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Carbon-carbon (C-C) bond forms the 'backbone' of nearly every organic molecule, and lies at the heart of the chemical sciences! This transformation has always been one of the most useful and fundamental reactions in the development of organic chemistry. Currently, the concept of 'green chemistry' is globally acclaimed and has already advanced quite significantly to come out as a distinct branch of chemical sciences. Among the principles of 'green chemistry', one principle is dedicated to "design of energy efficiency" -that is to develop synthetic strategies that require less/minimum amount of energy to carry out a specific reaction with optimum productivity. And the most effective way-out to save energy is to develop strategies/protocols that are capable enough to carry out the transformations at ambient temperature and pressure! As part of on-going developments on green synthetic strategies, designing for reactions under ambient conditions coupled with other green aspects is, thus, an area of current choice. This review is aimed to offer an up-to-date development on the design of carbon-carbon bond forming protocols to access a wide variety of organic molecules of topical significance under ambient conditions. The account highlights on the brilliant applications of reaction conditions such as the use of solvents or no solvent, catalysts or no catalyst, and the use of green tools like ball-milling, ultrasonication and visible light in achieving the goal! Design for Carbon Carbon Frameworks at Ambient ConditionsN Me Me Me O O COOH Br Br (Graphic for TOC)

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Section: Addition Reactionsmentioning

confidence: 99%

Design for carbon–carbon bond forming reactions under ambient conditions

Brahmachari

2016

RSC Adv.

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“…Thus, the development of a general approach to the synthesis of 5-functionalized 1,2-dihydropyrimidin-2-ones is important. Taking into consideration the reported formation of imines from α-trichloromethyl-substituted secondary amines and amides by elimination of chloroform in the presence of bases [33][34][35][36], we hypothesized that 5-functionalized 1,2-dihydropyrimidin-2-ones (1b,c R 2 = H) could be obtained starting from the corresponding 4-trichloromethyl-1,2,3,4-tetrahydropyrimidin-2-ones. Synthesis of the latter is presented in our retrosynthetic plan (Scheme 1) and includes ureidoalkylation of enolates of α-functionalized ketones [37][38][39][40][41].…”

Section: Introductionmentioning

confidence: 99%

A New Approach to 5-Functionalized 1,2-Dihydropyrimidin-2-ones/imines via Base-Induced Chloroform Elimination from 4-Trichloromethyl-1,2,3,4-tetrahydropyrimidin-2-ones/imines

Solovyev¹,

Fesenko

Шуталев

2018

22nd International Electronic Conference on Synthetic Organic Chemistry

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A novel four-step methodology for the synthesis of 5-acyl- and 5-arylsulfonyl-1,2-dihydropyrimidin-2-ones has been developed. The reaction of readily available N-[(1-acetoxy-2,2,2-trichloro)ethyl]-ureas with Na-enolates of 1,3-diketones, β-oxoesters, or α-arylsulfonylketones followed by heterocyclization–dehydration of the oxoalkylureas formed gave 5-acyl- or 5-arylsulfonyl-4-trichloromethyl-1,2,3,4-tetrahydropyrimidin-2-ones. The latter, in the presence of strong bases, eliminates CHCl3 to give the target compounds. The above methodology was also used in the synthesis of 5-acyl-1,2-dihydropyrimidin-2-imines starting from N-[(1-acetoxy-2,2,2-trichloro)ethyl]-N′-guanidine.

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“…This type of transformation was earlier realized for acyclic 2,2,2-trichloroethylamines. 12,13 Scheme 3…”

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confidence: 99%

A Convenient Access to 3-(Trihalomethyl)-3-phenyl-3,4-dihydro-2H-1,4-benzoxazines/thiazines and Chlorinated 3-Phenyl-2,3-dihydro-1,5-benzoxazepines/thiazepines by an Aziridination-Selective-Ring-Opening Sequence

Shinkevich¹,

Новиков²,

Khlebnikov³

2007

Synthesis

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Aziridine ring opening with N-C(1) bond breaking in 1,1-dichloro-1a-phenyl-1a,2-dihydro-1H-azirino[2,1-c][1,4]benzoxazine and -benzothiazine proceeds under the action of hydrohalo acid to give 3-trihalomethyl derivatives of 1,4-benzoxazine and thiazine. When the same compounds react with boron trifluoride etherate, the ring expansion with N-C(1a) bond breaking takes place with formation of 3,4-dichloro-3-phenyl-2,3-dihydro-1,5-benzoxazepine and -1,5-benzothiazepine. These are convenient precursors for the synthesis of 4-substituted 1,5-benzoxazepine and 1,5-benzothiazepine derivatives via reaction with nucleophiles.

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Reactions of 1-trichloromethyl-substituted amines with potassium tert-butoxide.

Cited by 15 publications

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Design for carbon–carbon bond forming reactions under ambient conditions

Design for carbon–carbon bond forming reactions under ambient conditions

A New Approach to 5-Functionalized 1,2-Dihydropyrimidin-2-ones/imines via Base-Induced Chloroform Elimination from 4-Trichloromethyl-1,2,3,4-tetrahydropyrimidin-2-ones/imines

A Convenient Access to 3-(Trihalomethyl)-3-phenyl-3,4-dihydro-2H-1,4-benzoxazines/thiazines and Chlorinated 3-Phenyl-2,3-dihydro-1,5-benzoxazepines/thiazepines by an Aziridination-Selective-Ring-Opening Sequence

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Reactions of 1-trichloromethyl-substituted amines with potassium tert-butoxide.

Cited by 15 publications

References 0 publications

Design for carbon–carbon bond forming reactions under ambient conditions

Design for carbon–carbon bond forming reactions under ambient conditions

A New Approach to 5-Functionalized 1,2-Dihydropyrimidin-2-ones/imines via Base-Induced Chloroform Elimination from 4-Trichloromethyl-1,2,3,4-tetrahydropyrimidin-2-ones/imines

A Convenient Access to 3-(Trihalomethyl)-3-phenyl-3,4-dihydro-2H-1,4-benz­oxazines/thiazines and Chlorinated 3-Phenyl-2,3-dihydro-1,5-benzoxazepines/thiazepines by an Aziridination-Selective-Ring-Opening Sequence

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A Convenient Access to 3-(Trihalomethyl)-3-phenyl-3,4-dihydro-2H-1,4-benzoxazines/thiazines and Chlorinated 3-Phenyl-2,3-dihydro-1,5-benzoxazepines/thiazepines by an Aziridination-Selective-Ring-Opening Sequence