Synthesis of N-Alkyl-1,3-dihydro-2,1-benzisoxazoles

Title	Synthesis of N-Alkyl-1,3-dihydro-2,1-benzisoxazoles
Authors	Thomas D. Beckler, David Crich
Magazine	Organic Letters
Date	11/05/2024
DOI	10.1021/acs.orglett.4c03509
Introduction	This study outlines an efficient synthesis method for N-alkyl-1,3-dihydro-2,1-benzisoxazoles and their precursors derived from methyl 2-nitrobenzoates. The process involves partial nitro reduction using hydrazine and rhodium on carbon to produce hydroxylamines, followed by base-induced cyclization to form benzisoxazol-3(1H)-ones. Alkylation under basic conditions precedes the reduction step, which employs lithium aluminium hydride in the presence of trimethylsilyl chloride to yield the final 1,3-dihydrobenzisoxazoles.
Quote	Thomas D. Beckler and David Crich. Synthesis of N-alkyl-1,3-dihydro-2,1-benzisoxazoles. Org. Lett. 2024. DOI: 10.1021/acs.orglett.4c03509
Element	Carbon (C) , Rhodium (Rh) , Hydrogen (H) , Lithium (Li)
Materials	Chemical Compounds
Industry	Chemical Manufacturing

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