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US 2023/0339879 A1Published application
Substituted chromanes, analogs thereof, and methods of use and synthesis
AssigneeNorthwestern University
InventorsKarl A. Scheidt, Rick C. Betori, Benjamin R. McDonald
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Abstract
Disclosed are chromane compounds, analogs thereof, and methods of their synthesis and use. The compounds may be synthesized by methods involving reductive annulations of arylidene malonates with unsaturated electrophiles using photoredox/Lewis acid cooperative catalysis. The compounds may be formulated in a pharmaceutical composition for treating one of the aforementioned diseases or disorders.
Claims18
1-16. (canceled)
A method of synthesizing a compound of formula,
- or a salt or hydrate thereof,
- the method comprising reacting reagents comprising:
- (a) a compound having a formula selected from
- wherein:
- R1 and R2 are independently selected from hydrogen, alkyl, alkoxy, carboxy, and carboxyalkyl;
- R3 and R4 are independently selected from hydrogen, alkyl, alkoxy, carboxy, carboxyalkyl, aryl, carboxyalkylaryl (e.g., carboxybenzyl ester), and cyano;
- Optionally, wherein at least one of R1, R2, R3, and R4, is not hydrogen;
- R5, R6, R7, and R8 are independently selected from hydrogen, alkyl, alkoxy, halo and optionally R7 and R8 form an aryl group;
- X is selected from oxygen, nitrogen (NH), and carbon (CH2);
- and
- n is an integer selected from 0-1;
- (b) a photocatalyst;
- and
- (c) a Lewis acid;
- wherein the reagents react in a cooperative Lewis acid/photoredox reductive enolate annulation reaction.
12 more elements
Dependencies are inferred from the claim text.