- Chemoselective Schwartz Reagent Mediated Reduction of Isocyanates to Formamides
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Addition of the in situ generated Schwartz reagent to widely available isocyanates constitutes a chemoselective, high-yielding, and versatile approach to the synthesis of variously functionalized formamides. Steric and electronic factors or the presence of sensitive functionalities (esters, nitro groups, nitriles, alkenes) do not compromise the potential of the method. Full preservation of the stereochemical information contained in the starting materials is observed. The use of formamides in the nucleophilic addition of organometallic reagents (Chida-Sato allylation, Charette-Huang addition to imidoyl triflate activated amides, Matteson homologation of boronic esters) is briefly investigated.
- Pace, Vittorio,De La Vega-Hernández, Karen,Urban, Ernst,Langer, Thierry
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supporting information
p. 2750 - 2753
(2016/06/15)
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- Highly efficient four-component synthesis of 4(3H)-quinazolinones: Palladium-catalyzed carbonylative coupling reactions
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Given the importance of quinazolinones and carbonylative transformations, a palladium-catalyzed fourcomponent carbonylative coupling system for the synthesis of diverse 4(3H)-quinazolinone in a concise and convergent fashion has been developed. Starting from 2-bromoanilines (1 mmol), trimethyl orthoformate (2 mmol), and amines (1.1 mmol), under 10 bar of CO, the desired products were isolated in good yields in the presence of Pd(OAc)2 (2 mol%), BuPAd2 (6 mol%) in 1,4-dioxane (2 mL) at 1008C, using N,Ndiisopropylethylamine (2 mmol) as the base. Notably, the process tolerates the presence of various reactive functional groups and is very selective for quinazolinones, and was used in the synthesis of the precursor to the bioactive dihydrorutaempine.
- He, Lin,Li, Haoquan,Neumann, Helfried,Beller, Matthias,Wu, Xiao-Feng
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p. 1420 - 1424
(2014/03/21)
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- A simple method for preparation of ZnO nanoparticles as a highly efficient nanocatalyst for N-formylation of primary and secondary amines under solvent-free condition
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A convenient reaction between alky, aryl, and heteroalkyl amines and formic acid as a formylating agent in the presence of catalytic amount of mechanochemically synthesized zinc oxide nanoparticles under solvent-free condition for the synthesis of corresponding N-formyl derivatives is described. Copyright Taylor and Francis Group, LLC.
- Alinezhad, Heshmatollah,Salehian, Fatemeh
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p. 532 - 538
(2013/07/19)
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- A novel method for preparing isocyanides from N-substituted formamides with chlorophosphate compounds
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Treatment of N-substituted formamides with chlorophosphate compounds such as PhOPOCl2, EtOPOCl2, Me2NPOCl2, and (PhO)2POCl and tertiary amines such as triethylamine, pyridine, and N,N-diisopropylethylamine produced the corresponding isocyanides in high yields. This method can be used to prepare various alkyl and aryl isocyanides. Georg Thieme Verlag Stuttgart · New York.
- Kobayashi, Genki,Saito, Tateo,Kitano, Yoshikazu
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experimental part
p. 3225 - 3234
(2011/11/30)
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- Synthesis of 4-hydroxy-3-quinolinecarboxylic acid derivatives by a condensation/cyclization sequence between o-isocyanobenzoates and magnesium enolates
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Addition of magnesium ester and amide enolates, generated using an excess amount of a magnesium amide (from diisopropylamine and ethylmagnesium bromide), to o-isocyanobenzoates affords 4-hydroxy-3-quinolinecarboxylic esters and amides by a tandem Claisen-type condensation/cyclization sequence.
- Kobayashi, Kazuhiro,Nakashima, Toshio,Mano, Masaaki,Morikawa, Osamu,Konishi, Hisatoshi
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p. 602 - 603
(2007/10/03)
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