Michel Legraverend

Microwave-assisted Pd/Cu-catalyzed C-8 direct alkenylation of purines and related azoles: an alternative access to 6,8,9-trisubstituted purines.

An efficient microwave-assisted palladium/copper comediated C-8 direct alkenylation of purines with styryl bromides has been developed. The method is regioselective, functional group tolerant, rapid, and compatible with other related azoles. Combined with subsequent nucleophilic substitution, it provides an easy access to new 6,8,9-trisubstituted purines.

Synthesis of 6,7,8-Trisubstituted Purines via a Copper-Catalyzed Amidation Reaction

We report herein an efficient method for the synthesis of 6,7,8-trisubstituted purines via a copper-catalyzed amidation reaction from easily accessible starting materials. Furthermore, the resulting 6-benzylsulfanyl-substituted purine derivatives may be readily oxidized for substitution by nucleophiles to give access to 6,7,8-trisubstituted purines for biological screening purposes.

Synthesis of Ring-enlarged Cyclobut-A and Cyclobut-G Analogues as HIV Inhibitors. Part 4

Two ring-expanded analogues (compouds 13 and 14)of the anti-HIV agents cyclobut-A and cyclobut-G are described. They were synthesized from trans-3,4-bis-(hydroxymethyl)cyclobutylamine which was obtained from threo-3,4-bis(methoxycarbonyl)-hexane dioic acid. Neither compound (13, 14) was able to provide protection to CEM cells against HIV-1 infection

High-Yielding Two-Step Synthesis of 6,8-Disubstituted N-9-Unprotected Purines

We report herein a convenient method for the synthesis of libraries of 6,8-disubstituted-9-H-purines in two steps, including cyclization of 6-chloro-4,5-diaminopyrimidine with various arylcarboxylic acids or chlorides, followed by S(N)Ar with amines and alkoxides or Pd-catalyzed amidations at C-6. These reactions were highly efficient and allowed the synthesis of a 32-member library of 6,8-disubstituted purines.

Synthesis of Carbocyclic Oxetanocin Analogues as Potential Anti-HIV Agents. Part 3

Two new carbocyclic oxetanocin analogues have been prepared from 1-amino-3-methylenecyclobutane. The results of biological testing against HIV-1 2 in vitro are presented