Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams.

Herein we present the direct asymmetric synthesis of tetrazole-functionalized 1-deoxynojirimycin derivatives from simple sugars via a Schwartz's reagent-mediated reductive amide functionalization followed by a variant of the Ugi-azide multicomponent reaction. The anomeric configurations of two products were unambiguously confirmed by X-ray analysis. This work also describes examples of interesting further transformations of the title products.

General synthesis of 2,1-benzisoxazoles (anthranils) from nitroarenes and benzylic C-H acids in aprotic media promoted by combination of strong bases and silylating agents.

Carbanions of phenylacetonitriles, benzyl sulfones, and dialkyl benzylphosphonates add nitroarenes at the ortho-position to the nitro group to form [Formula: see text]-adducts that, upon treatment with trialkylchlorosilane and additional base (t-BuOK or DBU), transform into 3-aryl-2,1-benzisoxazoles in moderate-to-good yields.

Synthesis of pyrrolo[3,2-]phenazines from 5-nitroindoles and anilines.

Abstract: Anilines react with 5-nitroindoles in the presence of -BuOK in ,-dimethylformamide (DMF) to form 5-nitroso-4-arylaminoindoles that in turn when treated with ,-bis(trimethylsilyl)acetamide cyclize to pyrrolo[3,2-]phenazines. In an alternative approach pyrrolo[3,2-]phenazines are formed from aminoindoles and nitroarenes.