A method for C2 acylation of 1,3-indandiones

The 1,3-indandione scaffold is an important structural motif used in the preparation of a large number of industrial chemical and pharmaceutical compounds. However, few approaches allow for the direct C2 acylation on these building blocks. A method was developed using DMAP and EDCI, which is mild in...

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Bibliographic Details
Published in:Tetrahedron 2018-05, Vol.74 (22), p.2762-2768
Main Authors: Larsen, Brian J., Rosano, Robert J., Ford-Hutchinson, Thomas A., Reitz, Allen B., Wrobel, Jay E.
Format: Article
Language:English
Subjects:
2-Acyl-1,3-indandione
Acylation
Carboxylic acid
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Summary:The 1,3-indandione scaffold is an important structural motif used in the preparation of a large number of industrial chemical and pharmaceutical compounds. However, few approaches allow for the direct C2 acylation on these building blocks. A method was developed using DMAP and EDCI, which is mild in reactivity, covers a diverse range of carboxylic acid acylating agents, is compatible with electron releasing and withdrawing substituents on the 1,3-indandione partner, and performs well in a polar aprotic solvent (for solubility reasons) This method cleanly afforded twenty five different products in yields of 32–96%. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.04.041