1227807-92-2Relevant academic research and scientific papers
Copper(I)-Catalyzed Asymmetric Vinylogous Aldol-Type Reaction of Allylazaarenes
Wang, Si-Qing,Liu, Zong-Ci,Yue, Wen-Jun,Yin, Liang
supporting information, p. 4604 - 4608 (2021/01/21)
A vinylogous aldol-type reaction of allylazaarenes and aldehydes is disclosed that affords a series of chiral γ-hydroxyl-α,β-unsaturated azaarenes in moderate to excellent yields with high to excellent regio- and enantioselectivities. With (R,RP)-TANIAPHOS and (R,R)-QUINOXP* as the ligand, the carbon-carbon double bond in the products is generated in (E)-form. With (R)-DTBM-SEGPHOS as the ligand, (Z)-form carbon-carbon double bond is formed in the major product. In this vinylogous reaction, aromatic, α,β-unsaturated, and aliphatic aldehydes are competent substrates. Moreover, a variety of azaarenes, such as pyrimidine, pyridine, pyrazine, quinoline, quinoxaline, quinazoline, and benzo[d]imidazole are well-tolerated. At last, the chiral vinylogous product is demonstrated as a suitable Michael acceptor towards CuI-catalyzed nucleophilic addition with organomagnesium reagents.
Synthesis of 4-allylquinazolines from N-(2-cyanoaryl)amides via the In-mediated allylation of nitrile and dehydrative cyclization cascade
Kim, Sung Hwan,Kim, Se Hee,Kim, Taek Hyeon,Kim, Jae Nyoung
scheme or table, p. 2774 - 2777 (2010/07/06)
The reaction of allylindium reagents and N-(2-cyanoaryl)amides afforded 2-substituted-4-allylquinazolines in good yields via the indium-mediated Barbier-type allylation of nitrile and the following dehydrative cyclization cascade.
