77651-75-3Relevant articles and documents
Lewis acid-catalyzed generation of C-C and C-N bonds on π-deficient heterocyclic substrates
Staderini, Matteo,Bolognesi, Maria Laura,Menndez, J. Carlos
supporting information, p. 185 - 195 (2015/01/30)
Focused microwave irradiation of a series of halogenated nitrogen heterocycles and different kinds of nucleophiles in the presence of a catalytic amount of indium trichloride leads to the efficient and completely regioselective generation of aromatic C-C and C-N bonds. The method is simple, rapid, general and inexpensive, and can be performed without the use of dried solvents. Most of the synthetized compounds are new and in many cases the work-up required only filtration. Furthermore, this is the first example of the use of a Lewis acid as a catalyst for heteroarylation, vinylation and amination reactions on π-deficient heterocyclic substrates.
The scope and mechanism of phosphonium-mediated SNAr reactions in heterocyclic amides and ureas
Wan, Zhao-Kui,Wacharasindhu, Sumrit,Levins, Christopher G.,Lin, Melissa,Tabei, Keiko,Mansour, Tarek S.
, p. 10194 - 10210 (2008/04/12)
(Chemical Equation Presented) An efficient "one-step" synthesis of cyclic amidines and guanidines has been developed. Treatment of cyclic amides and ureas with benzotriazol-l-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), base, and nitrogen nucleophiles leads to the formation of the corresponding cyclic amidines and guanidines, typically in good to excellent yields. This method has also been used to prepare heteroaryl ethers and thioethers using phenol and thiophenol nucleophiles. Time course NMR and HPLC-MS studies have facilitated explicit characterization of the proposed intermediates (the phosphonium salt and HOBt adduct); the data reveal a stepwise reaction pathway.
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.