The reaction of primary, secondary, allylic and benzylic trityl ethers 1 with lithium powder and a catalytic amount of naphthalene led to reductive cleavage of the trityl-oxygen bond, affording the corresponding alcohols 2 in good to excellent yields under very mild reaction conditions. The detritylation process could successfully be extended to several hydroxy, alkoxy and amino functionalised trityl ethers. This methodology represents a new and efficient detritylation procedure under non-acidic reaction conditions.

No abstract

No abstract

On treatment with indium metal in MeOH/THF, the trityl group undergo reductive removal from 1-H protected tetrazoles; (including aliphatic, aromatic and heteroaromatic substituents), affording the corresponding free tetrazoles in excellent yields, without any decomposition of the tetrazole ring or reduction of any other group.

Abstract:The reaction of N-tritylated tetrazoles (bearing aliphatic, aromatic and heteroaromatic substituents, including a functionalised one) with lithium powder and a catalytic amount of naphthalene led to reductive removal of the trityl group, affording the corresponding free tetrazoles in excellent yields without decomposition of the tetrazole ring. The detritylation process could successfully be extended to several tetrazoles that are components of Sartans, which are an interesting kind of drugs. The chemoselectivity between the trityl-tetrazol and the trityl-amine bond cleavages was also studied. This methodology represents an efficient deprotection of tritylated tetrazole under non-acidic reaction conditions.