15190-13-3Relevant articles and documents
Straightforward α-Amino Nitrile Synthesis Through Mo(CO)6-Catalyzed Reductive Functionalization of Carboxamides
Trillo, Paz,Slagbrand, Tove,Adolfsson, Hans
, p. 12347 - 12351 (2018/09/10)
The selective reduction of amides into an intermediate hemiaminal catalyzed by Mo(CO)6 together with the inexpensive and easy to handle TMDS (1,1,3,3-tetramethyldisiloxane) as reducing agent, followed by subsequent trapping of the hemiaminal with a cyanide source, allows for the straightforward synthesis of α-amino nitriles. The methodology presented here, displays high levels of chemoselectivity allowing for the reduction of amides in the presence of functional groups such as ketones, imines, aldehydes, and acids, which affords a simple route for the synthesis of α-amino nitriles with a broad scope of functionalities in high yields. Furthermore, the applicability of this methodology is demonstrated by scale up experiments and by derivatization of the target compounds into synthetically interesting products. The selective cyanation is successfully applied in late stage functionalizations of amide containing drugs and prolinol derivatives.
Aged red wine pigments as a source of inspiration for organic synthesis - The cases of the color-stable pyranoflavylium and flavylium-(4→8)-flavan chromophores
Chassaing, Stefan,Isorez-Mahler, Géraldine,Kueny-Stotz, Marie,Brouillard, Raymond
, p. 3066 - 3078 (2015/05/04)
Two flavylium-based chromophores peculiar to aged red wine pigments are investigated from a synthetic viewpoint. The condensation between easy-to-prepare 5-hydroxy-4-methylflavylium salts and aldehydes, giving birth to color-stable pyranoflavylium pigments, further proves efficient and wide in scope. A set of some twenty structurally-related flavylium-based pigments has been prepared and structure:color relationships are discussed. Furthermore, the synthesis of the flavylium-(4→8)-flavan chromophore is achieved via a novel three-step sequence. The elaborated sequence starts with an iodine-magnesium exchange from an 8-iodinated flavan, thus generating a magnesiated species that then smoothly reacts with a flavone to furnish an adduct, that finally leads to the expected chromophore via dehydration.
Propylphosphonic anhydride (T3P) catalyzed one-pot synthesis of α-aminonitriles
Reddy, Sirigireddy Sudharsan,Reddy, Bhoomireddy Rajendra Prasad,Reddy, Peddiahgari Vasu Govardhana
, p. 739 - 743 (2015/08/03)
Abstract The Strecker reaction was performed via a one-pot three component condensation of hetero aromatic/aromatic aldehydes, secondary amines and trimetylsilyl cyanide in the presence of propylphosphonic anhydride (T3P) to accomplish the corresponding α-aminonitriles. The main advantages of this method are very short reaction time and excellent yields.
A fast and benign synthesis of α-aminonitriles by reusable immobilized AlCl3on γ-Al2O3
Pamar, M. Geeta,Govender,Pillay,Abrahamse,Nanjundaswamy
, p. 110 - 116 (2015/01/30)
Reusable, immobilized AlCl3 on γ-Al2O3 is generated by the reaction of AlCl3 on activated γ-Al2O3 of 58 A at 600°C. This is an efficient, catalytic, safe and environmentally acceptable catalyst for the synthesis of a series of α-aminonitriles utilizing Strecker's process by the reaction of carbonyl compounds, amines and trimethylsilyl cyanide (TMSCN) with excellent yields at ambient temperature. The catalyst can be easily recycled and has been reused for thirteen runs without losing its activity.
Chirally deuterated benzyl chlorides from benzyl alcohols via hexachloroacetone/polymer-supported triphenylphosphine: Synthesis of protected (2S, 3S)-[3-2H, 15N]-tyrosine
Barnett, Derek W.,Refaei, Maryanne S.,Curley Jr., Robert W.
, p. 6 - 11 (2013/03/28)
Chirally deuterated benzyl chlorides were prepared using novel, general hexachloroacetone/polymer-supported triphenylphosphine treatment of chirally deuterated benzyl alcohols. Doubly labeled protected tyrosine was obtained in 62% yield with 86% de at the α-carbon and 82% de at the β-carbon. Key in the synthesis was the alkylation of 15N-labeled (-)-8-phenylmenthylhippurate with R-(-)-4-triisopropylsilyloxybenzyl-α-d chloride. Chirally deuterated benzyl chlorides were prepared in high yield with inversion from benzyl alcohols using solid-phase methods. One of the benzyl chlorides obtained was used in the synthesis of protected tyrosine labeled with 15N and chirally deuterated on the β-position. Copyright
Silica-bonded N-propyl diethylenetriamine sulfamic acid as a recyclable solid acid catalyst for the synthesis of α-aminonitriles
Rahi, Tahere,Baghernejad, Mojtaba,Niknam, Khodabakhsh
, p. 1095 - 1100 (2013/01/14)
Silica-bonded N-propyl diethylenetriamine sulfamic acid (SBPDSA) is employed as a recyclable catalyst to synthesize a-aminonitriles. These syntheses involved one-pot condensation of an aldehyde, an amine, and trimethylsilyl cyanide under mild reaction conditions at room temperature. SBPDSA was recycled seven times in the condensation of benzaldehyde, aniline, and trimethylsilyl cyanide without reduction of its catalytic activity.
Silica-Bonded N-Propyl Diethylenetriamine Sulfamic Acid as a Recyclable Solid Acid Catalyst for the Synthesis of α-Aminonitriles
Rahi, Tahere,Baghernejad, Mojtaba,Niknam, Khodabakhsh
, p. 1095 - 1100 (2015/06/30)
Silica-bonded N-propyl diethylenetriamine sulfamic acid (SBPDSA) is employed as a recyclable catalyst to synthesize a-aminonitriles. These syntheses involved one-pot condensation of an aldehyde, an amine, and trimethylsilyl cyanide under mild reaction conditions at room temperature. SBPDSA was recycled seven times in the condensation of benzaldehyde, aniline, and trimethylsilyl cyanide without reduction of its catalytic activity.
Improved synthesis of (R)-glycine-d-15N
Walker, Joel R,Curley Jr., Robert W
, p. 6695 - 6701 (2007/10/03)
Previously, we have synthesized the title glycine to permit assignment of the prochiral α-protons of glycine residues in the NMR study of the protein FKBP. A key, and low yielding step in this synthesis occurs in the ruthenium tetraoxide mediated degradation of N-t-Boc-p-methoxybenzyl amine to N-t-Boc-glycine. Efforts to improve this key step by exploring different substrates and N-protecting groups were successful to render this synthesis amenable for the large scale production of (R)-glycine-d-15N.
A Practical Large Scale Chemical Synthesis of Chiral Glycines
Ramalingam, Kondareddiar,Nanjappan, Palaniappagownder,Kalvin, Douglas M.,Woodard, Ronald W.
, p. 5597 - 5604 (2007/10/02)
(R)- and (S)-2H>glycine of high chiral purity were synthesized in large quantities in ca.40percent overall yield from readily available starting materials via a totally chemical procedure.Reduction of either 2H>-furfural or 2H>-4-methoxybenzaldehyde with either (+) or (-)-B-isopinocampheyl-9-borabicyclononane gave chiral arylmethyl alcohols which were converted into their respective phthaloyl amino derivatives of the opposite configuration at the methylene carbon via the Mitsunobu reaction.The aromatic groups were oxidatively unmasked to give their corresponding glycine derivatives by either ozone or ruthenium tetraoxide oxidation.
