- Rediscovering aminal chemistry: Copper(ii) catalysed formation under mild conditions
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Aminals, the N,N analogues of acetals, have been thoroughly explored in organic chemistry, with a particular focus on heteroaromatic aldehyde lithiation. Nevertheless, the existing methodologies for their formation typically employ harsh conditions limiting their usefulness. In this work, we present an efficient and mild methodology for the preparation of aminals from aromatic aldehydes, including furanic platforms. These mild conditions allowed ease of access to a plethora of aminals and as such we set out to explore previously unaccessible potential applications. By studying the stability of various aminals, we were able to develop a simple aldehyde protecting group based on a commercial diamine which is deprotected under mind conditions. We developed a protocol for the scavenging of genotoxic aldehydes by taking advantage of our methodology and a diamine resin, as well as early studies on the development of a stimuli-responsive release system using a salycil aldehyde derived aminal. This journal is
- Afonso, Carlos A. M.,António, Jo?o P. M.,Gomes, Rafael F. A.,Mendon?a, Ricardo,Pereira, Juliana G.
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supporting information
p. 7484 - 7490
(2020/11/18)
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- Solvent-free synthesis of monoacylaminals from the reaction of amides and aminals as precursors in carbinolamide synthesis
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A solvent-free method of generating monoacylaminals by heating the amide and aminal starting materials in the presence of one another has been developed. Yields were generally between 45% and 65% with the monoacylaminal being isolated, needing no further purification after drying under high vacuum.
- Sansone, Matthew F.,Koyanagi, Takaoki,Przybyla, David E.,Nagorski, Richard W.
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supporting information; experimental part
p. 6031 - 6033
(2010/11/21)
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- A new protocol for the preparation of aminals from aromatic aldehydes and their facile conversion to phosphonates
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A new and fast method for the preparation of aminals is reported from the reaction of aromatic aldehydes and secondary amines in the presence of potassium carbonate in high yields. The aminal can be converted to the corresponding iminum salt in reaction with acetyl chloride very easily and in very short time with high yield. Addition of trialkylphosphite, as one possible nucleophile, to the prepared iminium salt produces the α-amino phosphonate in very high yield.
- Dezfuli, Mohammad Karimi,Saidi, Mohammad Reza
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- Process for the preparation of Grignard reagents and novel Grignard reagents
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Grignard reagents which contain a protected aldehyde function are obtained in a particularly advantageous manner from a halogenated aldehyde by reaction with a secondary monoamine to give an open-chain aminal, and conversion of the latter into a Grignard
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- Novel synthesis of α-acetylstyrylphosphonates
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α-Acetylstyrylphosphonates were conveniently synthesized from 2-oxopropylphosphonates and substituted (dimorpholinomethyl)-benzenes (animals). 4-Benzylidenemorpholinium carboxylates, generated from animals by the action of α-halo acids, reacted with the phosphonates to give the products by elimination of the amine. The yields were influenced by the nature of substituents and their position in the phenyl ring and could be improved by adjustment of the acidities of the reacted acids. α-Acetylstyrylphosphonates containing various substituents on every position (at the 2-, 3-, or 4-position) in the phenyl ring were obtained generally in excellent yields using monochloroacetic acid.
- Sakoda,Matsumoto,Seto
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p. 705 - 713
(2007/10/02)
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