316173-79-2Relevant academic research and scientific papers
Diastereoselective aziridination of cyclic dienes with 3-acetoxyaminoquinazolin-4(3H)-ones: Competitive formation of insertion products from cyclohexadienes
Atkinson,Meades
, p. 7769 - 7772 (2000)
Aziridination of cyclopentadiene and cycloheptadiene with 3-acetoxyamino-2-[(S)-1-hydroxy-2,2-dimethylpropyl]quinazolin-4(3H)-one 1 in the presence of titanium(IV) tert-butoxide gave the corresponding vinyl aziridines highly diastereoselectively: the corresponding aziridination product of cyclohexa-1,3-diene is formed less diastereoselectively and is accompanied by a by-product 9 from formal insertion into an allylic C-H bond, a previously unobserved reaction type for 3-acetoxyaminoquinazolinones. (C) 2000 Elsevier Science Ltd.
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 (2007/10/03)
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.
