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Literature DB >> 29760536

A Method for C2 Acylation of 1,3-Indandiones.

Brian J Larsen¹, Robert J Rosano¹, Thomas A Ford-Hutchinson², Allen B Reitz², Jay E Wrobel².

Abstract

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%.

Entities: CellLine Chemical Disease Species

Year: 2018 PMID： 29760536 PMCID： PMC5947957 DOI： 10.1016/j.tet.2018.04.041

Source DB: PubMed Journal: Tetrahedron ISSN： 0040-4020 Impact factor: 2.457

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References

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9 in total

A Method for C2 Acylation of 1,3-Indandiones.

1. Synthesis and evaluation of indenopyrazoles as cyclin-dependent kinase inhibitors. 3. Structure activity relationships at C3(1,2).

2. Synthesis and evaluation of indenopyrazoles as cyclin-dependent kinase inhibitors. 2. Probing the indeno ring substituent pattern.

3. Potent, selective and orally bioavailable leucine-rich repeat kinase 2 (LRRK2) inhibitors.

4. A novel cell-permeable, selective, and noncompetitive inhibitor of KAT3 histone acetyltransferases from a combined molecular pruning/classical isosterism approach.

5. Synthesis of and tautomerism in 3-acyltetramic acids.

Review 6. The molecular diversity scope of 1,3-indandione in organic synthesis.

7. Isomeric solid enols on ring- and amide-carbonyls of substituted 2-carbanilido-1,3-indandiones.

8. SmCl3-catalyzed C-acylation of 1,3-dicarbonyl compounds and malononitrile.

9. Palladium-Catalyzed Carbonylative Annulation Reactions Using Aryl Formate as a CO Source: Synthesis of 2-Substituted Indene-1,3(2H)-dione Derivatives.