88-68-6Relevant articles and documents
Glucose as an Eco-Friendly Reductant in a One-Pot Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones
dos Santos, Thiago,Grundke, Caroline,Lucas, Tobias,Gro?mann, Luca,Clososki, Giuliano Cesar,Opatz, Till
supporting information, p. 6429 - 6432 (2020/09/02)
Carbohydrates such as glucose are an abundant renewable resource that can be employed in synthetic processes as a source of carbon and/or hydrogen to yield products of high economical and biological impact. Herein, we report a versatile and environmentally friendly protocol for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones, a privileged scaffold in medicinal chemistry, based on the use of glucose as an eco-friendly reductant in alkaline aqueous medium. This method can be viewed as a blueprint for the development of further one-pot sequences involving glucose as a reductant.
Efficient Synthesis of Quinazolinones by Transition-Metal-Free Direct Aerobic Oxidative Cascade Annulation of Alcohols with o-Aminoarylnitriles
Wang, Qi,Lv, Miao,Liu, Jianping,Li, Yang,Xu, Qing,Zhang, Xu,Cao, Hongen
, p. 3043 - 3048 (2019/03/17)
A mild and atom-economic method was developed for direct and efficient synthesis of quinazolinones through a transition-metal-free aerobic oxidative cascade annulation reaction of widely available o-aminoarylnitriles and alcohols. Air could be employed as an effective oxidant under mild conditions, generating water as the only byproduct. Possibly owing to the “cesium effect”, the water-soluble base CsOH was found to be crucial in all key steps of the reaction mechanism. Because a wide range of substrates can be used to prepare substituted quinazolinones without contamination by transition-metal residues, this method may be of interest for application in pharmaceutical synthesis. Possible reaction paths were also proposed according to control reactions.
Vasicine from Adhatoda vasica as an organocatalyst for metal-free Henry reaction and reductive heterocyclization of o-nitroacylbenzenes
Sharma, Sushila,Kumar, Manoranjan,Bhatt, Vinod,Nayal, Onkar S.,Thakur, Maheshwar S.,Kumar, Neeraj,Singh, Bikram,Sharma, Upendra
supporting information, p. 5003 - 5008 (2016/10/25)
Vasicine, a quinazoline alkaloid, from the leaves of Adhatoda vasica, has been utilized as an efficient catalyst for metal and base free Henry reaction of various aldehydes with nitro alkanes. The method can be used in the synthesis of various β-nitro alcohols under mild reaction conditions without use of hazardous organic solvents and expensive catalysts. Vasicine is also applied successfully for one pot synthesis of 2,1-benzisoxazoles from o-nitroacylbenzenes in good yields under mild conditions.