67117-05-9Relevant academic research and scientific papers
A Divergent Nickel-Catalyzed Synthesis of Quinazolinediones and Benzoxazinone Imines
Wertjes, William,Ayers, Sloan,Gao, Qi,Simmons, Eric M.,Beutner, Gregory L.
, p. 4453 - 4461 (2018)
During exploration of the nickel(0)-catalyzed reaction of isocyanates and isatoic anhydrides, it was found that changes in the substitution pattern of the isocyanate led to constitutionally isomeric quinazolinediones [quinazoline-2,4(1 H,3 H)-diones] or benzoxazinone imines [2-imino-1,2-dihydro-4 H -3,1-benzoxazin-4-ones]. Ligand and solvent screening experiments allowed for identification of conditions that could lead to each constitutional isomer in good to excellent levels of selectivity and yield. Comprehensive characterization of the previously poorly characterized benzoxazinone imines is also provided.
Pd(ii)-Catalyzed [4 + 1 + 1] cycloaddition of simple: O -aminobenzoic acids, CO and amines: Direct and versatile synthesis of diverse N -substituted quinazoline-2,4(1 H,3 H)-diones
Ding, Qianqian,Fan, Xuesen,Wang, Jinjun,Yang, Jingyi,Zhang, Guisheng,Zhang, Xiaopeng
, p. 526 - 535 (2021/01/28)
The mild, efficient, and straightforward synthesis of pharmaceutically and biologically active N3-substituted and N1,N3-disubstituted quinazoline-2,4-(1H,3H)-diones from simple and readily available substrates has been a huge challenge. Described here is a Pd(ii)-catalyzed [4 + 1 + 1] modular synthesis of diverse quinazoline-2,4-(1H,3H)-diones through one-pot cascade reactions of cyclocondensation of o-(alkyl)aminobenzoic acids with CO, amidation of the intermediate isatoic anhydrides with amines, and unprecedented carbonylation of the resulting o-aminobenzamides with CO under 1 atm and 60 °C conditions. The chemoselective and versatile multicomponent reaction allows for the diversities of the products including N3-substituted and N1,N3-disubstituted products, and even makes the substituents on N1,N3 the same or different from each other, which cannot be achieved by most traditional synthetic strategies. This journal is
Method for synthesizing quinazoline-2, 4 (1H, 3H)-diketone compound
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Paragraph 0022-0028, (2020/12/30)
The invention discloses a method for synthesizing a quinazoline-2, 4 (1H, 3H)-diketone compound, and belongs to the technical field of synthesis of nitrogen-containing heterocyclic compounds. According to the technical scheme, the method is characterized in that an anthranilic acid compound and an amine compound serve as reaction raw materials, CO serves as a carbonylation reagent, Pd (II) servesas a catalyst, KI or KI/AcOH serves as an additive, Cu (OAc) 2 or O2 or Cu (OAc) 2/O2 serves as an oxidizing agent, and the target product quinazoline-2, 4 (1H, 3H)-diketone compound is prepared through a one-pot multi-component reaction. The method has the advantages of simple and easily available raw material, short synthesis route, high atom economy and step economy, mild reaction conditions, diversified product structures, high yield of most target products and the like.
