Detection of Isotopic Atropisomerism Based on ortho-H/D Discrimination.

Racemic and optically active 3-(2-deuteriophenyl)-2-(1-phenylpropan-2-yl)quinazoline-4-thiones were prepared. The nuclear magnetic resonance spectra clearly show that they exist as a 1:1 mixture of diastereomers due to the isotopic atropisomerism based on ortho-H/D discrimination (N-C axial chirality) and a chiral carbon.

Thionation of Optically Pure N-C Axially Chiral Quinazolin-4-one Derivatives with Lawesson's Reagent.

The reaction of various optically pure N-C axially chiral quinazolin-4-one derivatives with Lawesson's reagent proceeded without a marked decrease in optical purity to give optically active quinazoline-4-thione derivatives (93-99% ee) possessing a high rotational barrier in good yields.

A catalyst-free bis(triflyl)ethylation/benzannulation reaction: rapid access to carbazole-based superacidic carbon acids from alkynols.

Carbazoles possessing Tf2CHCH2 groups were obtained by the reaction of 1-(indol-2-yl)but-3-yn-1-ols with in situ-generated Tf2C[double bond, length as m-dash]CH2 through vicinal difunctionalisation of the alkyne moiety, where the vinyl-type carbocation intermediate was selectively attacked by the indole moiety and not by the carbanion moiety.