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US 6,660,871 B2Granted
Synthesis of 4H-chromene derivatives
AssigneeThomas Jefferson Unversity
InventorZiwei Huang
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Abstract
Substituted 4H-chromene derivatives are a new class of compounds that bind to Bcl-2 protein and induce apoptosis in tumor cells. The present invention is directed to an efficient synthetic method for the preparation of these compounds from salicylaldehyde derivatives and alkyl cyanoacetates under solid phase.
Claims10
A method for preparing a 4H-chromene derivative comprising the steps
- a) combining a salicylaldehyde derivative, an alkyl cyanoacetate and a suitable molecular sieve to form said 4H-chromene derivative;
- and
- b) isolating said 4H-chromene derivative.
A method of preparing a 4H-chromene derivative of a formula:
- from a salicylaldehyde derivative of a formula:
- and an alkyl cyanoacetate of a formula:
- NC—CH2—COOR3
- wherein,
- R1 and R2 are selected from the group consisting of hydrogen, CH2CH═CH2, CF2Br, OCH3, NO2, Cl, and Br;
- and
- R3 is selected from the group consisting of hydrogen, CH2CH3, CH2CH2CH2CH3, C(CH3)3, CH2Ph and CH2CH2OCH3;
- comprising the steps of
- a) suspending said salicylaldehyde derivative in a first solvent;
- b) combining said salicylaldehyde derivative suspension with said alkyl cyanoacetate to form a first reaction mixture;
- c) adding a molecular sieve into said first reaction mixture to form a second reaction mixture;
- d) stirring said second reaction mixture;
- e) filtering off said molecular sieve from said second reaction mixture;
- f) washing said filtered molecular sieve from step e) at least one time with a second solvent and collecting filtrates;
- g) removing said second solvent from said filtrates from step f) to form a residue;
- h) solidifying said residue;
- and
- i) crystallizing said solidified residue.
15 more elements
Dependencies are inferred from the claim text.