- Three-component strategy toward 5-membered heterocycles from isocyanide dibromides.
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A three-component strategy starting from isocyanides allows a straightforward synthesis of five-membered ring heterocycles. New cascades were developed involving the addition of a nitrogenated nucleophile-an azide or a tetrazole-on isocyanide dibromides,
- Kaim, Laurent El,Grimaud, Laurence,Patil, Pravin
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- Synthesis of Bis(α-alkylaminobenzylidene)hydrazines and their Transformation into 4-Alkyl-4H-1,2,4-triazoles
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Sterically hindered 4-alkyl-3,5-diphenyl-4H-1,2,4-triazoles have been prepared by reacting bis(α-chlorobenzylidene)hydrazine with alkylamines.Under mild conditions this reaction gives, as intermediates, bis(α-alkylaminobenzylidene)hydrazines, a new class of compound.The stability of these compounds appeared to increase with increasing bulk of the alkyl substituent.Upon being heated the compounds, either neat or in a variety of solvents, were transformed into the corresponding triazoles in high yields.Bis(α-alkylaminobenzylidene)hydrazines with sterically bulky groups, e.g. tert-butyl or 1-adamantyl, undergo cyclization in conjuction with elimination to form, as the major product, 3,5-diphenyl-1H-1,2,4-triazole.
- Gautun, Odd Reidar,Carlsen, Per H. J.
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p. 609 - 615
(2007/10/02)
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