53693-72-4Relevant academic research and scientific papers
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
Copper-Catalyzed Oxidative Cyclization of 2-Aminobenzamide Derivatives: Efficient Syntheses of Quinazolinones and Indazolones
Duraisamy, Tamilselvan,Govindan, Karthick,Jayaram, Alageswaran,Lin, Wei-Yu,Senadi, Gopal Chandru
supporting information, (2021/12/02)
A simple copper-catalyzed assembly to formulate quinazolinone and indazolone derivatives in a single protocol manner is reported. These transformations are based on the fact that DMF can serve as a reaction solvent and one carbon synthon for the construct
Integration of Bromine and Cyanogen Bromide Generators for the Continuous-Flow Synthesis of Cyclic Guanidines
Glotz, Gabriel,Lebl, René,Dallinger, Doris,Kappe, C. Oliver
supporting information, p. 13786 - 13789 (2017/10/09)
A continuous-flow process for the in situ on-demand generation of cyanogen bromide (BrCN) from bromine and potassium cyanide that makes use of membrane-separation technology is described. In order to circumvent the handling, storage, and transportation of elemental bromine, a continuous bromine generator using bromate–bromide synproportionation can optionally be attached upstream. Monitoring and quantification of BrCN generation was enabled through the implementation of in-line FTIR technology. With the Br2 and BrCN generators connected in series, 0.2 mmol BrCN per minute was produced, which corresponds to a 0.8 m solution of BrCN in dichloromethane. The modular Br2/BrCN generator was employed for the synthesis of a diverse set of biologically relevant five- and six-membered cyclic amidines and guanidines. The set-up can either be operated in a fully integrated continuous format or, where reactive crystallization is beneficial, in semi-batch mode.
Palladium-Catalyzed Ortho-Selective C-H Oxidative Carbonylation of N-Substituted Anilines with CO and Primary Amines for the Synthesis of o-Aminobenzamides
Zhang, Xiaopeng,Dong, Shuxiang,Niu, Xueli,Li, Zhengwei,Fan, Xuesen,Zhang, Guisheng
supporting information, p. 4634 - 4637 (2016/09/28)
An efficient, one-pot strategy with high selectivity and high atom economy for the synthesis of o-aminobenzamides has been developed via palladium-catalyzed ortho-selective C-H oxidative carbonylation of N-substituted anilines with CO and primary amines. A wide range of N-substituted anilines and primary amines can be tolerated in this transformation to afford the corresponding o-aminobenzamides in moderate to excellent yields under mild conditions.
A facile IL-DMSO assisted synthesis of 5-, 6-, and 7-membered benzo-annelated cyclic guanidines
Verma, Amit,Giridhar, Rajani,Modh, Pratik,Yadav, Mange Ram
supporting information; experimental part, p. 2954 - 2958 (2012/07/28)
A new and facile IL-DMSO assisted method has been developed for the synthesis of biologically important cyclic guanidines like 2-aminobenzimidazole, 2-imino-4-quinazolinone, and 2-imino-5-benzotriazepinones at ambient temperatures. The desired products could be obtained by microwave irradiation32 also, but at elevated temperatures. A plausible mechanism for catalysis has been proposed.
