77642-40-1Relevant academic research and scientific papers
Samarium diiodide promoted synthesis of N,N′-disubstituted amidines
Xu, Fan,Sun, Jianhua,Shen, Qi
, p. 1867 - 1869 (2007/10/03)
An efficient one-step preparation of an N,N′-disubstituted amidine by the direct nucleophilic addition of an amine to the parent nitrile using catalytic amounts of SmI2 under relatively mild conditions is developed. Alkyl, benzyl and aryl amidi
Use of Lanthanide(III) Ions as Catalysts for the Reactions of Amines with Nitriles
Forsberg, John H.,Spaziano, Vincent T.,Balasubramanian, Trichey M.,Liu, Gordon K.,Kinsley, Steven A.,et al.
, p. 1017 - 1021 (2007/10/02)
Catalytic amounts of lanthanide(III) triflates promote reactions between amines and nitriles leading to a variety of products.The Ln3+ ions activate weakly coordinating nitriles at large amine: Ln3+ mole ratios, even in the presence of amines that form thermodynamically stable complexes with Ln3+ ions.The reactions involving primary monoamines and diamines appear to be general and provide a viable synthetic route to N,N'-disubstituted amidines (2) and cyclic amidines (4), respectively.Symmetrically substituted triazines (8 or 9) are observed as byproducts in some of these systems when the reactions are carried out by using excess nitrile.Secondary alicyclic amines or dimethylamine reacts with acetonitrile to yield pyrimidines (6) and 2,4,6-trimethyl-s-triazine (8).Two routes to triazine have been proposed, one involving the reaction of ammonia with the nitrile and the second involving the reaction of an amidine (1 or 5) with the nitrile.The ability of Ln3+ ions to activate nitriles under conditions that oppose nitrile coordination is attributed to the lability of Ln3+ complexes derived from N-donors.
Phosphoramides. XIII. Phosphorus Pentaoxide-Amine Hydrochloride Mixtures as Reagents in the Synthesis of 4(3H)-Quinazolinones and 4-Quinazolinamines
Nielsen, Knud Erik,Pedersen, Erik B.
, p. 637 - 642 (2007/10/02)
4(3H)-Quinazolinones 3a-r have been prepared by heating methyl N-acylanthranilates 1a-c and the hydrochlorides of primary aliphatic and aromatic amines with phosphorus pentaoxide and N,N-dimethylcyclohexylamine at 180 deg C. 4-Quinazolinamines 4 and the amidine 7 were isolated as by-products.The carboxamides 5 and 6 were believed to be reaction intermediates.By raising the temperature to 250 deg C 4 was obtained in a preparative yield.
