254115-37-2Relevant academic research and scientific papers
N-heterocyclic carbene-catalyzed hydroacylation of unactivated double bonds
Hirano, Keiichi,Biju, Akkattu T.,Piel, Isabel,Glorius, Frank
supporting information; experimental part, p. 14190 - 14191 (2010/02/15)
(Chemical Equation Presented) An intramolecular N-heterocyclic carbene (NHC)-catalyzed hydroacylation of unactivated double bonds is reported. Systematic variation of the catalyst structure revealed an N- mesitylthiazolylidene annulated with a seven-membered ring to be especially reactive. This NHC enables a unique C-C bond-forming reaction to afford substituted chroman-4-ones in moderate to excellent yields, even ones containing all-carbon quaternary centers.
SYNTHESIS OF 2-AMINO-SUBSTITUTED 4-OXO-4H-CHROMEN-8.YL-TRIFLUORO-METHANESULFONIC ACID ESTERS
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Page/Page column 34, (2008/06/13)
A method of synthesising a compound of formula (I): wherein RN1 and RN2 are independently selected from hydrogen, an optionally substituted C1-7 alkyl group, C3-20 heterocyclyl group, or C5-20 aryl group, or may together form, along with the nitrogen atom to which they are attached, an optionally substituted heterocyclic ring having from 4 to 8 ring atoms; from a compound of formula (III): comprising the steps of: (a) removing the allyl group from the compound of formula (III) with appropriate reaction conditions to yield a compound of formula (II):; and (b) reacting the compound of formula (II) with a triflating agent to yield a compound of formula (I).
Judicious application of allyl protecting groups for the synthesis of 2-Morpholin-4-yl-4-oxo-4H-chromen-8-yl triflate, a key precursor of DNA-dependent protein kinase inhibitors
Aristegui, Sonsoles Rodriguez,El-Murr, Marine Desage,Golding, Bernard T.,Griffin, Roger J.,Hardcastle, Ian R.
, p. 5927 - 5929 (2007/10/03)
(Chemical Equation Presented) 2-Morpholin-4-yl-4-oxo-4H-chromen-8-yl 2,2,2-trifluoromethanesulfonate is a key intermediate for the synthesis of the DNA-dependent protein kinase (DNA-PK) inhibitor 8-dibenzothiophen-4-yl-2- morpholin-4-yl-chromen-4-one (NU7441). Two improved methods for the synthesis of this triflate have been developed: (A) in 35% overall yield, through modification of the published route, and (B) in 15% overall yield, by a new route employing a Baker-Venkataraman rearrangement to enable generation of the chromenone scaffold. Both syntheses depend on the judicious use of allyl protecting groups.
