The synthesis and biological evaluation as antiviral agents of a series of racemic 4-aryl-1,2,3-triazolo-2',3'-dideoxy-2'-iodocarbanucleosides and 4-aryl-1,2,3-triazolo-2',3'-dideoxy-2',3'-didehydrocarbanucleosides is presented. These compounds were produced using a click chemistry approach, with the iodoazide 13a as the key intermediary.

Nucleic acids U 0700Synthesis of 4-Substituted-1,2,3-triazole Carbanucleoside Analogues of Ribavirin via Click Chemistry. -The route to the title triazoles involves a haloazidation reaction of pentene (I) that affords the desired relative stereochemistry with regard to the hydroxymethyl group in the key intermediate (III) (major product). In the presence of a catalytic amount of CuI, it reacts with arylalkynes (IV) to give only one of the possible regioisomers, i.e. the desired iodotriazoles (V). Dehydroiodination with DABCO also generates only one of the possible regioisomers in all cases. Most of the products do not exhibit any specific antiviral effects against several viruses. -(PEREZ-CASTRO, I.; CAAMANO*, O.; FERNANDEZ, F.; GARCIA, M. D.; LOPEZ, C.; DE CLERCQ, E.; Org. Biomol. Chem. 5 (2007) 23, 3805-3813; Dep. Quim. Org., Fac. Farm.

Dedicated to Professor Benito Alcaide on the occasion of his 60th birthday AbstractThe synthesis and biological evaluation as antiviral agents of a series of racemic 4-aryl-1,2,3-triazolyl carbanucleosides of type (±)-10/(±)-11 related to the broad spectrum antiviral agent ribavirin 1 are described. These compounds were produced using a "click chemistry" strategy starting from readily available protected alcohol 13b. The synthetic approach made use of olefinbased organic reactions for the stereoselective construction of the appropriately functionalized cyclopentane ring moiety followed by copper (I) catalyzed Huisgen 1,3-dipolar cycloaddition of azides and alkynes for the regioselective construction of the heterocyclic triazole moiety.

Cyclocondensation of (±)-exo,exo-5,6-(Isopropylidenedioxy)-3-(pyrrolidinomethylene)bicyclo[2.2.1]heptan-2-one with N-C-N Dinucleophiles (±)-2-P h e n y l-6 , 7-d i h y d r o-5 H-c y c l o p e n t a [ d ] p y r i m i d i n e-5 , 7-d i m e t h a n o l

Two new 6-aryl-substituted 1¢(N)-homocarbanucleosides were prepared by Suzuki-Miyaura reactions of the protected 6-halopurine derivatives with phenylboronic acids. Additionally, 1¢(N)-homocarbanucleosides of 6-chloropurine, 2-amino-6-chloropurine and 3-benzoyluracil were prepared by Mitsunobu reaction with a protected diol. From the uracil derivative, the corresponding 5-bromo-and 5-iodouracil compounds were also obtained.