79323-12-9Relevant academic research and scientific papers
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)
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.
Ruthenium-Catalyzed Synthesis of Pyrrolo[1,2- A [quinoxaline Derivatives from 1-(2-Aminophenyl)pyrroles and Sulfoxonium Ylides
Cui, Xin-Feng,Hu, Fang-Peng,Huang, Guo-Sheng,Zhan, Zhen-Zhen,Zhou, Xiao-Qiang
supporting information, p. 1205 - 1210 (2020/07/20)
A ruthenium-catalyzed [5+1] annulation of 1-(2-aminophenyl)pyrroles with α-carbonyl sulfoxonium ylides is reported. This reaction provides a one-step method for synthesizing pyrrolo[1,2- A [quinoxaline derivatives under ambient conditions. The system proceeds with a short reaction time and a high functional-group tolerance. Notably, this divergent protocol tolerates β-keto sulfoxonium ylides and can be applied to α-ester sulfoxonium ylides. A preliminary study was made of the mechanism of the reaction, and a reaction pathway is proposed.
Iodine-mediated oxidative Pictet-Spengler reaction using terminal alkyne as the 2-oxoaldehyde surrogate for the synthesis of 1-aroyl-β-carbolines and fused-nitrogen heterocycles
Dighe, Shashikant U.,Samanta, Surya K.,Kolle, Shivalinga,Batra, Sanjay
, p. 2455 - 2467 (2017/04/03)
An efficient iodine-mediated oxidative Pictet-Spengler reaction in dimethyl sulphoxide (DMSO) using terminal alkynes as the 2-oxoaldehyde surrogate for the synthesis of aryl (9H-pyrido[3,4-b]indol-1-yl)methanones is described. The scope of the protocol includes the total synthesis of Fascaplysin, Eudistomins Y1 and Y2. The methodology is extended for preparing pyrrolo[1,2-a]-quinoxaline and indolo[1,5-a]quinoxaline derivatives. The utility of 1-aroyl-β-carbolines was demonstrated by performing palladium-catalyzed β-carboline directed ortho-C(sp2)-H functionalization of the phenyl ring with thiomethyl (SMe) group using DMSO as source and for accessing 4-aryl-canthin-6-ones.
Synthesis of pyrrolo[1,2-a]quinoxaline derivatives by lewis acid-catalyzed reactions of 1-(2-isocyanophenyl)pyrroles
Kobayashi,Irisawa,Matoba,Matsumoto,Yoneda,Morikawa,Konishi
, p. 1109 - 1114 (2007/10/03)
1-(2-Isocyanophenyl)pyrroles have been prepared. They react in moderate to good isolated yields with aldehydes (or ketones), oxiranes, and acetals in the presence of catalytic amounts of diethyl ether-boron trifluoride to give pyrrolo [1,2-a]quinoxalines carrying an oxyalkyl substituent, such as α-hydroxyalkyl, β-hydroxyalkyl, or α-alkoxyalkyl, at the 4-position.
Reissert Compound Studies. XLI. Synthesis and Reactions of the Pyrroloquinoxaline Reissert Compound and its Analogs.
Veeraraghavan, S.,Popp, F. D.
, p. 775 - 777 (2007/10/02)
Reaction of pyrroloquinoxaline, either by the phase-transfer catalyst method or by the trimethylsilyl cyanide method, yielded the Reissert compound, 5-benzoyl-4-cyano-4,5-dihydropyrroloquinoxaline.This Reissert compound rearranged to 4-benzo
