Aluminum selenide reaction with nitriles

In Older to avoid the handling of poisonous hydrogen selenide, two other useful syntheses have been devised. One method uses the reaction of aromatic nitriles with aluminum selenide in the presence of pyridine, triethylamine and water (Scheme 24), while the other is performed by the reaction of nitriles with selenium, carbon monoxide and water in the presence of triethylamine (Scheme 25). These methods are exceedingly convenient in terms of manipulation without the isolation of hydrogen selenide for the preparation of selenoamides. Using these methods, a variety of aromatic and heterocyclic selenoamides can be obtained from the corresponding nitriles in high yields. 

Advancements in the Hantzsch method have appeared in the literature since 1982. An improved synthesis of the aryl- and alkylselenoamide precursors by reaction of the nitrile with aluminum selenide <85JOC384> or NaHSe prepared in situ from NaBH4 and selenium <93S870> has been reported. In particular the latter method aids in the synthesis of 2-alkylselenazoles because of the instability... 

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