Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction)

Ballini, Roberto; Petrini, Marino

doi:10.1016/j.tet.2003.11.016

Cited by 435 publications

(200 citation statements)

References 174 publications

(130 reference statements)

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“…Both signals confirm that the organic groups were covalently bonded onto the silica surface. The other two peaks are attributed to pure surface signals described as: i) Si(OSi) 4 , Q 4 at -104 ppm; ii) surface signal, Si(OSi) 3 OH, Q 3 at -96 ppm. 19,23 Important information about immobilization of pendant groups on the inorganic structure of the catalyst can be obtained through solid state 13 C NMR spectra, as presented in Figure 4.…”

Section: Synthesis and Characterization Of The Catalystmentioning

confidence: 99%

“…The relatively high acidity of the nitro group and its facile transformation into various functionalities have extended the importance of nitro compounds and these have proven to be valuable intermediates for the preparation of complex molecules [1][2][3][4][5] and to serve as precursors, extensively used in the agrochemical, pharmaceutical and dyestuff industries. 6 Thus, a great interest in these kinds of synthetic processes has been shown in recent years.…”

Section: Introductionmentioning

confidence: 99%

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Tetramethylguanidine covalently bonded onto silica gel as catalyst for the addition of nitromethane to cyclopentenone

Oliveira¹,

Torres²,

Silva³

et al. 2006

J. Braz. Chem. Soc.

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Um catalisador baseado em sílica quimicamente modificada com tetrametilguanidina (TMG) foi sintetizado pela co-condensação de tetraetilortossilicato (TEOS) com um novo agente sililante, preparado pela reação entre a molécula TMG e (3-cloropropil)trimetoxisilano. O direcionador n-dodecilamina foi utilizado para organizar a polimerização do catalisador inorgânico-orgânico. A termogravimetria mostrou que o número de sítios ativos do catalisador foi de 1,35 mmol g .A espectroscopia na região do infravermelho e de ressonância magnética nuclear no estado sólido para os núcleos 29 Si e 13 C confirmou a obtenção do produto desejado. Este material foi usado para catalisar a adição de nitrometano em ciclopentenona. 98% de conversão foi observada depois de 3 h de reação. O catalisador foi recuperado e reutilizado por mais catorze vezes, mantendo uma eficiência catalítica em torno de 98%.A catalyst based on silica chemically modified with tetramethylguanidine (TMG) was synthesized by the co-condensation of tetraethylorthosilicate (TEOS) with a new silylant agent derived from the reaction between the TMG molecule and (3-chloropropyl)trimethoxysilane. A neutral n-dodecylamine template was used to organize the polymerization of the inorganicorganic catalyst. Thermogravimetry showed that the number of active pendant groups in the catalyst was 1.35 mmol g -1 , with a surface area of 811 ± 75 m 2 g -1. Infrared spectroscopy and 13 C and 29 Si nuclear magnetic resonance data are in agreement with the proposed structure. This material has been used to catalyse the addition of nitromethane to cyclopentenone. The catalytic efficiency was followed and the nitromethylcyclopentanone conversion presented a yield of 98% at 3 h of reaction. The catalyst was recovered and reused 14 times, maintaining about 98% of its catalytic efficiency.

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Section: Synthesis and Characterization Of The Catalystmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Tetramethylguanidine covalently bonded onto silica gel as catalyst for the addition of nitromethane to cyclopentenone

Oliveira¹,

Torres²,

Silva³

et al. 2006

J. Braz. Chem. Soc.

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“…An efficient synthetic approach toward such compounds is through the nitro-Mannich (aza-Henry) reaction. The nucleophilic addition of nitroalkanes to imines generates ␤-nitroamine derivatives (31), which are readily converted into 1,2-diamines or ␣-amino carbonyl compounds by the reduction of the nitro group (32,33) or through the Nef reaction (34).…”

mentioning

confidence: 99%

Cu-catalyzed cross-dehydrogenative coupling: A versatile strategy for C–C bond formations via the oxidative activation of sp ³ C–H bonds

Bohle

2006

Proc. Natl. Acad. Sci. U.S.A.

582

159

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“…Приєднання нітроалканів до іміносполук, ві-доме під назвою реакції аза-Генрі або нітро-Ман-ніха, є ефективним варіантом одержання β-ніт-роамінів -важливих субстратів тонкого органіч-ного синтезу [1][2][3][4][5]. 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].…”

Section: -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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Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction)

Cited by 435 publications

References 174 publications

Tetramethylguanidine covalently bonded onto silica gel as catalyst for the addition of nitromethane to cyclopentenone

Tetramethylguanidine covalently bonded onto silica gel as catalyst for the addition of nitromethane to cyclopentenone

Cu-catalyzed cross-dehydrogenative coupling: A versatile strategy for C–C bond formations via the oxidative activation of sp ³ C–H bonds

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

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Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction)

Cited by 435 publications

References 174 publications

Tetramethylguanidine covalently bonded onto silica gel as catalyst for the addition of nitromethane to cyclopentenone

Tetramethylguanidine covalently bonded onto silica gel as catalyst for the addition of nitromethane to cyclopentenone

Cu-catalyzed cross-dehydrogenative coupling: A versatile strategy for C–C bond formations via the oxidative activation of sp 3 C–H bonds

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

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Cu-catalyzed cross-dehydrogenative coupling: A versatile strategy for C–C bond formations via the oxidative activation of sp ³ C–H bonds