4.5 Article

Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

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BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 19, 期 -, 页码 1677-1693

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BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.19.123

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[3+2] cycloaddition; decarboxylation; 1,3-dipolar; double cycloaddition; one-pot synthesis; multicomponent reaction; semi-stabilized azomethine ylide

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This article highlights recent work on the development of alpha-amino acid-based [3 + 2] cycloaddition reactions of N-H-type AMYs in multicomponent, one-pot, and stepwise reactions for the synthesis of diverse heterocycles related to some bioactive compounds and natural products.
The [3 + 2] cycloadditions of stabilized azomethine ylides (AMYs) derived from amino esters are well-established. However, the reactions of semi-stabilized AMYs generated from decarboxylative condensation of alpha-amino acids with arylaldehydes are much less explored. The [3 + 2] adducts of alpha-amino acids could be used for a second [3 + 2] cycloaddition as well as for other post-con-densation modifications. This article highlights our recent work on the development of alpha-amino acid-based [3 + 2] cycloaddition reactions of N-H-type AMYs in multicomponent, one-pot, and stepwise reactions for the synthesis of diverse heterocycles related to some bioactive compounds and natural products.

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