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We describe a new method for the preparation of dihydroquinazoline-2-thione and 4H-3,1-benzothiazine-2-thione derivatives by intramolecular heteroconjugate addition of carbodiimides or isothiocyanates bearing one o-substituted α,β-unsaturated carbonyl fragment promoted by the CS 2 /TBAF system.
Condensation of 1,1'-diacetylferrocene with o-azidobenzaldehyde under appropriate conditions leads either to the [5]-ferrocenophane 2 or the bis(azide) 3, as the only reaction products. Compound 2 undergoes an intramolecular aza-Wittig reaction to give the new type of cryptand 4. Bis(azide) 3 is converted into the macrocycle 5 by a Staudinger reaction with bis(diphenylphosphino)ethane; alternatively,...
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