234-95-7Relevant articles and documents
Cheeseman,Roy
, p. 856 (1969)
Transition-metal-free N-arylation: A general approach to aza-fused poly-heteroaromatics
Annareddygari, Srikanth,Kasireddy, Venkateshwer Reddy,Reddy, Jayachandra
, p. 3267 - 3276 (2019)
A new and efficient method for the synthesis of various aza-fused poly-hetero aromatics has been described. This protocol includes an intermolecular condensation followed by metal-free base-promoted intramolecular C―N coupling reaction. The advantage of this one-pot transformation lies in the use of simple cyclic amidines-like compounds without prefunctionalization of the starting heterocycles.
Efficient copper-catalyzed annulation of 2-formylazoles with 2-haloanilines for the synthesis of pyrrole- and imidazole-fused quinoxalines
Li, Zihao,Yan, Nannan,Xie, Jianwei,Liu, Ping,Zhang, Jie,Dai, Bin
, p. 589 - 593 (2015)
Promoted by CuI/2-hydroxybenzohydrazide catalytic system, a variety of pyrrole- and imidazole-fused quinoxalines have been efficiently one-pot synthesized from pyrrole-/imidazole-2-carboxaldehyde and 2-haloanilines in moderate to excellent yields. 2-Hydroxybenzohydrazide-promoted CuI-catalyzed one-pot annulation of pyrrole-/imidazole-2-carboxaldehyde with 2-haloanilines for the synthesis of pyrrolo[1,2-α]- and imidazo[1,2-α]quinoxalines under relatively mild conditions is described.
N,N-Dimethylformamide as Carbon Synthons for the Synthesis ofN-Heterocycles: Pyrrolo/Indolo[1,2-a]quinoxalines and Quinazolin-4-ones
Ding, Chengcheng,Li, Shichen,Ma, Chen,Ren, Jianing,Wang, Yishou
, p. 16848 - 16857 (2021/12/06)
N,N-dimethylformamide (DMF) as synthetic precursors contributing especially the methyl, acyl, and amino groups has played a significant role in heterocycle syntheses and functionalization. In this protocol, a wide range of pyrrolo/indolo[1,2-a]quinoxalines and quinazolin-4-ones were obtained in moderate to good yields by using elemental iodine without any metal or peroxides. We considered thatN-methyl andN-acyl of DMF participate and complete the reaction separately through different mechanisms, which displayed potential still to be explored of DMF.
α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocyclesviadecarboxylative oxidative annulation reaction
Jung, Chanhyun,Jung, Jae-Kyung,Lee, Heesoon,Lee, Kiho,Lee, Seohu,Park, Yunjeong,Sim, Jaeuk,Viji, Mayavan,Vishwanath, Manjunatha
, p. 37202 - 37208 (2020/10/28)
A metal-free and efficient procedure for the synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and indolo[1,2-a]quinoxaline has been developed. The key features of our method include thein situgeneration of aldehyde from α-hydroxy acid in the presence of TBHP (tert-butyl hydrogen peroxide), and further condensation with various amines, followed by intramolecular cyclization and subsequent oxidation to afford the corresponding quinoxalines, quinazolinones derivatives in moderate to high yields.