Dearomatising rearrangements of lithiated thiophenecarboxamides.
Thiophene-3-carboxamides bearing allyl or benzyl substituents at nitrogen undergo dearomatising cyclisation on treatment with LDA. Rearrangements transform the dearomatised products into pyrrolinones, azepinones or partially saturated azepinothiophenes.
Clayden
Jonathan
J
Department of Chemistry, University of Manchester, Oxford Road, Manchester, UK M13 9PL. j.p.clayden@man.ac.uk
Turnbull
Rachel
R
Helliwell
Madeleine
M
Pinto
Ivan
I
D018360:Crystallography, X-Ray; D008094:Lithium / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013876:Thiophenes / Q000737:chemistry*
D009942:Organometallic Compounds; D013876:Thiophenes; D008094:Lithium