132387-93-0Relevant academic research and scientific papers
Multicomponent synthesis of 2-imidazolines
Bon, Robin S.,Van Vliet, Bart,Sprenkels, Nanda E.,Schmitz, Rob F.,De Kanter, Frans J. J.,Stevens, Christian V.,Swart, Marcel,Bickelhaupt, F. Matthias,Groen, Marinus B.,Orru, Romano V. A.
, p. 3542 - 3553 (2005)
(Chemical Equation Presented) A multicomponent reaction (MCR) between amines, aldehydes, and isocyanides bearing an acidic α-proton gives easy access to a diverse range of highly substituted 2-imidazolines. The limitations of the methodology seem to be de
Scope and limitations of reductive amination catalyzed by half-sandwich iridium complexes under mild reaction conditions
Nguyen, Dat P.,Sladek, Rudolph N.,Do, Loi H.
supporting information, (2020/07/15)
The conversion of aldehydes and ketones to 1° amines could be promoted by half-sandwich iridium complexes using ammonium formate as both the nitrogen and hydride source. To optimize this method for green chemical synthesis, we tested various carbonyl substrates in common polar solvents at physiological temperature (37 °C) and ambient pressure. We found that in methanol, excellent selectivity for the amine over alcohol/amide products could be achieved for a broad assortment of carbonyl-containing compounds. In aqueous media, selective reduction of carbonyls to 1° amines was achieved in the absence of acids. Unfortunately, at Ir catalyst concentrations of 1 mM in water, reductive amination efficiency dropped significantly, which suggest that this catalytic methodology might be not suitable for aqueous applications where very low catalyst concentration is required (e.g., inside living cells).
Graphene oxide: A convenient metal-free carbocatalyst for facilitating amidation of esters with amines
Patel, Khushbu P.,Gayakwad, Eknath M.,Shankarling, Ganapati S.
, p. 2661 - 2668 (2020/02/20)
Herein, we report a graphene oxide (GO) catalyzed condensation of non-activated esters and amines, that can enable diverse amides to be synthesized from abundant ethyl esters forming only volatile alcohol as a by-product. GO accelerates ester to amide conversion in the absence of any additives, unlike other catalysts. A wide range of ester and amine substrates are screened to yield the respective amides in good to excellent yields. The improved catalytic activity can be ascribed to the oxygenated functionalities present on the graphene oxide surface which forms H-bonding with the reactants accelerating the reaction. Improved yields and a wide range of functional group tolerance are some of the important features of the developed protocol.
Graphene Oxide: A Metal-Free Carbocatalyst for the Synthesis of Diverse Amides under Solvent-Free Conditions
Patel, Khushbu P.,Gayakwad, Eknath M.,Patil, Vilas V.,Shankarling, Ganapati S.
supporting information, p. 2107 - 2116 (2019/03/26)
An environmentally friendly, inexpensive, carbocatalyst, graphene oxide (GO) promoted efficient, metal-free transamidation of various carboxamides with aliphatic, cyclic, and aromatic amines is demonstrated. The protocol is equally applicable to phthalimide, urea, and thioamide determining its adaptability. The oxygenated functionalities such as carbonyl (?C=O), epoxy (?O?), carboxyl (?COOH) and hydroxyl (?OH), present on graphene oxide surface impart acidic properties to the catalyst. The graphene oxide being heterogeneous in nature, work efficiently under solvent-free reaction conditions providing desired products in good to excellent yields. The one-pot synthesis of 2,3-Dihydro-5H-benzo[b]-1,4-thiazepin-4-one moiety by GO catalyzed Aza Michael addition followed by intramolecular transamidation is also described. A plausible reaction mechanistic pathway involving H-bonding is discussed. The graphene oxide can be recycled and reused up to five cycles without much loss in catalytic activity. (Figure presented.).
Leuckart-Wallach Route Toward Isocyanides and Some Applications
Neochoritis, Constantinos G.,Zarganes-Tzitzikas, Tryfon,Stotani, Silvia,D?mling, Adrian,Herdtweck, Eberhardt,Khoury, Kareem,D?mling, Alexander
supporting information, p. 493 - 499 (2015/09/22)
Isocyanide-based multicomponent reactions (IMCR) are among the most important chemical reactions to efficiently generate molecular diversity and have found widespread use in industry and academia. Generally, isocyanides are synthesized in 1-2 steps starting from primary amines. Here, we provide experimental detail on an alternative approach toward formamides and, thus, isocyanides via the Leuckart-Wallach reaction in an improved variation. The resulting >50 synthesized and characterized formamides are useful starting materials for IMCR, as well as other chemistries. The advantage of using the Leuckart-Wallach pathway to formamides and isocyanides is the lower price, on average, of the starting materials, as well as their differential and complementary structural diversity, as compared to the primary amine pathway.
