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Efficient synthesis of 4-substituted-ortho-phthalaldehyde analogues: toward the emergence of new building blocks.

ABSTRACT: 4-Methoxy-ortho-phthalaldehyde and 4-hydroxy-ortho-phthalaldehyde are potentially useful molecules for fluorimetric analysis of a variety of amines and for the elaboration of complex molecular architectures. Nevertheless, literature generally describes their synthesis in very low yield (below 5%), mainly due to the inefficiency of the last oxidation step. In this paper, we report a reliable synthesis of 4-substituted-ortho-phthalaldehyde analogues in 51% overall yield owing to the addition of a protecting step of the unstable key intermediate 4,5-dihydroisobenzofuran-5-ol. Oxidation and deprotection steps were also studied in order to provide an effective availability of these two dialdehyde compounds that may increase their future applications.

SUBMITTER: Moitessier C

PROVIDER: S-EPMC6444388 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Efficient synthesis of 4-substituted-ortho-phthalaldehyde analogues: toward the emergence of new building blocks.

Moitessier Clémence C Rifai Ahmad A Danjou Pierre-Edouard PE Mallard Isabelle I Cazier-Dennin Francine F

Beilstein journal of organic chemistry 20190319

4-Methoxy-ortho-phthalaldehyde and 4-hydroxy-ortho-phthalaldehyde are potentially useful molecules for fluorimetric analysis of a variety of amines and for the elaboration of complex molecular architectures. Nevertheless, literature generally describes their synthesis in very low yield (below 5%), mainly due to the inefficiency of the last oxidation step. In this paper, we report a reliable synthesis of 4-substituted-ortho-phthalaldehyde analogues in 51% overall yield owing ...[more]

PMID: 30992719

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