13182-64-4Relevant articles and documents
Photoelectrochemical C?H Alkylation of Heteroarenes with Organotrifluoroborates
Yan, Hong,Hou, Zhong-Wei,Xu, Hai-Chao
, p. 4592 - 4595 (2019)
A photoelectrochemical method for the C?H alkylation of heteroarenes with organotrifluoroborates has been developed. The merger of electrocatalysis and photoredox catalysis provides a chemical oxidant-free approach for the generation and functionalization
Carbon-hydrogen bond insertion reactions of 3-acetoxyaminoquinazolin-4(3H)-ones with cyclic dienes: Stereochemistry and mechanism
Atkinson, Robert S,Meades, Christopher K
, p. 1415 - 1424 (2002)
Reaction of 2-substituted-3-acetoxyaminoquinazolin-4(3H)-ones (QNHOAc) with cyclohexa-1,3-diene or cyclohexa-1,4-diene (2equiv.) gives, besides the expected aziridination products, stable dihydroaromatic by-products formally arising by insertion of [QN?:] into one of the doubly allylic C-H bonds. An analogous insertion into the methylene C-H bonds of 9,10-dihydroanthracene or xanthene (1.5-2 equiv.) occurs. Using 3-acetoxyamino-2-[(S)-2,2-dimethyl-1-hydroxypropyl]quinazolin-4(3H)-one 2 (Q1NHOAc) in the presence of titanium(IV) t-butoxide, insertion into cyclohexa-1,3-diene takes place completely diastereoselectively and the configuration at the cyclohexadienyl ring carbon has been correlated with that at the 6-position of the major aziridine diastereoisomer co-produced in the reaction. A mechanism involving concerted insertion into the C-H bond of the diene by QNHOAc is proposed with endo-overlap of both double bonds of the diene with the Q group in the transition state.
Catalyst-free synthesis of quinazolinones by oxidative cyclization under visible light in the absence of additives
Yang, Jiangnan,Xie, Zongbo,Chen, Zhongsheng,Jin, Liang,Li, Qian,Le, Zhanggao
, p. 1496 - 1501 (2021/05/03)
A general metal-free oxidative cyclization route was developed to synthesize quinazolinones under visible light. A series of substituted 2-aminobenzamides were reacted with aldehydes or ketones to produce the desired quinazolinones in good yields. Most importantly, the reaction did not require excess oxidant or high temperatures.
Visible-light-mediated minisci C-H alkylation of heteroarenes with 4-alkyl-1,4-dihydropyridines using O2as an oxidant
Dong, Jianyang,Liu, Yuxiu,Song, Hongjian,Wang, Qingmin,Xu, Wentao,Yue, Fuyang
supporting information, p. 5599 - 5604 (2020/09/21)
Herein, we report a protocol for direct visible-light-mediated Minisci C-H alkylation reactions of N-heteroarenes with 4-alkyl-1,4-dihydropyridines at room temperature with molecular oxygen as an oxidant. The protocol permits efficient functionalization of various N-heteroarenes with a broad range of cyclic and acyclic primary, secondary, and tertiary alkyl groups and is scalable to the gram level. This mild protocol uses an inexpensive, green oxidant and is suitable for late-stage C-H alkylation of complex nitrogen-containing molecules. We demonstrated its utility by preparing or functionalizing several pharmaceuticals and natural products.
