New approaches to the synthesis of organofluorine nitrogenated derivatives

Fustero, Santos; Sanz‐Cervera, Juan F.; Piera, Julio; Sánchez‐Roselló, María; Chiva, Gema; Simón‐Fuentes, Antonio

doi:10.1016/j.jfluchem.2003.12.016

Cited by 25 publications

(4 citation statements)

References 46 publications

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“…Thus, selective synthetic procedures for fluorine‐containing cyclopentane, cyclohexane and cycloheptane β‐amino acids were developed when these types of derivatives were subjected to ring‐closing metathesis ,. Difluorinated β‐amino acid derivatives were synthetized by the ring‐closing metathesis of adduct (±)‐99 formed in the reaction of fluorinated imidoyl chlorides (±)‐98 and unsaturated esters, to give the corresponding difluorinated cis‐β‐aminocycloheptenecarboxylate (±)‐101 after reduction with NaCNBH 3 (Scheme ) …”

Section: Synthesis Of Fluorinated Cyclic β‐Amino Acid Derivatives By mentioning

confidence: 99%

Selective Synthesis of Fluorine‐Containing Cyclic β‐Amino Acid Scaffolds

Kiss

Fülöp

2017

The Chemical Record

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Fluorine-containing organic molecules have generated increasing impact in drug research over the past decade. Their preparation and development of novel synthetic methods towards new types of fluorinated molecules among them of β-amino acid derivatives has received large interest. Our research group have designed various highly selective and stereocontrolled methods for the construction of fluorine-containing cyclic β-amino acid derivatives. The synthetic approaches developed for the synthesis of various pharmacologically interesting cyclic β-amino acid derivatives as monomers with multiple stereogenic centers might be valuable protocols for the access of other classes of organic compounds.

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Section: Synthesis Of Fluorinated Cyclic β‐Amino Acid Derivatives By mentioning

confidence: 99%

Selective Synthesis of Fluorine‐Containing Cyclic β‐Amino Acid Scaffolds

Kiss

Fülöp

2017

The Chemical Record

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“…В останні два десятиліття пред-метом особливої уваги дослідників стали їх α-фто-роалкіловмісні аналоги -унікальні синтетичні блоки для побудови різноманітних типів фторо-ваних аміносполук [6][7][8]. Описані в літературі під-ходи до їх отримання зазвичай базуються на при-єднанні аміносполук до 3,3,3-трифторо-1-нітро-пропену (реакція аза-Міхаеля) [9][10][11][12][13].…”

Section: 1-трифторопропан-2-ил)кар-баматы; N-(3-амино-111-трифтороunclassified

Synthesis and some transformations of alkyl N-(2-aryl-3-nitro-1,1,1-trifluoropropan-2-yl)carbamates

Tkachuk¹,

Мельніченко²,

Kovalchuk³

et al. 2014

J. org. pharm. chem.

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Робота присвячена отриманню та дослідженню перетворень нових поліфункціональних фторовмісних синтез-блоків -алкіл N-(3-нітро-1,1,1-трифторопропан-2-іл) N-(2-АРИЛ-3-НИТРО-1,1,1-ТРИФТОРОПРОПАН-2-ИЛ -трифтороэтилиденкарбаматы; N-(3-нитро-1,1,1-трифторопропан-2-ил) кар-баматы; N-(3-амино-1,1,1-трифторопропан-2-ил)карбаматы; 4-трифторометилимидазолидин-2-оны; 3,3,3-трифторопропан-1,2-диамины Работа посвящена получению и исследованию преобразований новых полифункциональных фторсо-дер-жащих синтез-блоков -алкил N-(3-нитро-1,1,1-трифторопропан-2-ил) SYNTHESIS AND SOME TRANSFORMATIONS OF ALKYL N-(2-ARYL 6H 2 O leads to selective reduction of the nitro group and formation of the corresponding alkyl N-(3-aminopropan-2-yl)carbamates. The presence of amino group in their structure considerably affects the chemical shifts of diastereotopic methylene protons. Their signals in the 1 H NMR spectra are upfield (about 2 ppm difference in comparison with nitro derivatives). Alkyl N-(3-aminopropan-2-yl)carbamates in refluxing toluene in the presence of DBU were easily transformed into 4-trifluorometylimidazolidyn-2-ones by intramolecular cyclization. In its turn, tert-butyl N-(3-aminopropan-2-yl)carbamates when treating with hydrogen chloride in dioxane readily gave 3,3,3-trifluoropropan-1,2-diamines through Boc protecting group cleavage. СИНТЕЗ И НЕКОТОРЫЕ ПРЕВРАЩЕНИЯ АЛКИЛ

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“…6 The uracil-type herbicide has a substitutedpyrimidine-2,6-dione as common structural feature. 7 It has been recognized that the optimal substituent in pyrimidine-2,6-dione is trifluoromethyl group at 4-position, methyl at 3-position and multi-functionalized phenyl at 1-position. The trifluoromethyl group is the most favorable substituent, and enhances herbicidal activity markedly.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Herbicidal Activity of Novel N‐(2‐Fluoro‐5(3‐methyl‐2,6‐dioxo‐4‐(trifluoromethyl)‐2,3‐dihydro‐pyrimidin‐1(6H)‐yl)phenyl)‐2‐phenoxyacetamide Derivatives

Sun

Huang

et al. 2011

Chin. J. Chem.

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Thirteen novel N- (2-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)phenyl)-2-phenoxy)acetamides were designed and synthesized utilizing 4-fluoro-aniline and ethyl 3-amino-4,4,4-trifluorobut-2-enoate as starting materials. The chemical structures of all compounds were confirmed by 1 H NMR, IR, mass spectrum and elemental analyses. Subsequently, the herbicidal activities of the as-prepared compounds were evaluated in the greenhouse. Bioassay results indicated that most of compounds had better herbicidal activities against dicotyledonous weeds. Among all the tested compounds, compounds 4a-4i showed good herbicidal activities at both pre-emergence and post-emergence treatment against two or three kinds of dicotyledonous weeds, such as Abutilon theophrasti Medic, Amaranthus ascendens L, and Chenopodium album L at the dosage of 75 g ai/ha.

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New approaches to the synthesis of organofluorine nitrogenated derivatives

Cited by 25 publications

References 46 publications

Selective Synthesis of Fluorine‐Containing Cyclic β‐Amino Acid Scaffolds

Selective Synthesis of Fluorine‐Containing Cyclic β‐Amino Acid Scaffolds

Synthesis and some transformations of alkyl N-(2-aryl-3-nitro-1,1,1-trifluoropropan-2-yl)carbamates

Synthesis and Herbicidal Activity of Novel N‐(2‐Fluoro‐5(3‐methyl‐2,6‐dioxo‐4‐(trifluoromethyl)‐2,3‐dihydro‐pyrimidin‐1(6H)‐yl)phenyl)‐2‐phenoxyacetamide Derivatives

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