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US 2014/0350246 A1Published application
Nitrogen-containing heterocyclic compounds and methods of making the same
AssigneeBoard of Regents of the Nevada System of Higher Education, on behalf of the University of Nevada
InventorChristopher S. Jeffrey
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Abstract
The present invention relates to 7-membered nitrogen-containing heterocyclic compounds and methods of making the same. Using a novel aza-[4+3] cycloaddition reaction, the 7-membered heterocyclic compounds are synthesized by reacting a first reactant and a second reactant. Exemplary first reactants and second reactants include α-halohydroxamates and dienes, respectively.
Claims3
A heterocyclic compound represented by structural Formula (I):
- wherein
- R1 and R2 are the same or different and are independently selected from hydrogen, halide, a substituted or un-substituted alkyl, acyl, aryl, alkaryl, alkenyl, alkynyl, cycloalkyl, heteroalkyl, heterocycle, amino, amido, alkoxy, acyloxy, thio, or silyl, or R1 and R2 in combination form a cycloalkyl or a heterocycle;
- R3 is a substituted or unsubstituted alkyl, aryl, alkaryl, alkenyl, alkynyl, cycloalkyl, heteroalkyl, heterocycle, sulfinyl, sulfonyl, or silyl;
- R4 and R6 are the same or different and are independently selected from hydrogen, halide, a substituted or un-substituted alkyl, acyl, aryl, alkaryl, alkenyl, alkynyl, cycloalkyl, heteroalkyl, heterocycle, amino, amido, alkoxy, acyloxy, thio, or silyl;
- R5 and R7 combine to form a bridging moiety in a cyclic substructure, the bridging moiety including at least one of carbon, oxygen, nitrogen, or sulfur, wherein optionally R4 or R5 are covalently bonded to R1 or R2, or wherein optionally R6 or R7 are covalently bonded to R3;
- R8 and R9 are the same or different and are independently selected from hydrogen, halide, a substituted or un-substituted alkyl, acyl, aryl, alkaryl, alkenyl, alkynyl, cycloalkyl, heteroalkyl, heterocycle, amino, amido, alkoxy, acyloxy, thio, or silyl, or R8 and R9 combine to form a carbon-containing cyclic substructure;
- and
- Y is O, S, SO, or NR10, wherein R10 is a hydrogen, acyl, a substituted or unsubstituted alkyl, aryl, alkaryl, alkenyl, alkynyl, cycloalkyl, heteroalkyl, heterocycle, sulfinyl, sulfonyl, or silyl;
- wherein optionally R10 is covalently bonded to R6 or R7.
6 more elements
A [4+3] cycloaddition reaction product of
- a first reactant represented by general formula R1R2XC—CO—NHYR3, wherein R1 and R2 are the same or different and independently selected from hydrogen, halide, a substituted or un-substituted alkyl, acyl, aryl, alkaryl, alkenyl, alkynyl, cycloalkyl, heteroalkyl, heterocycle, amino, amido, alkoxy, acyloxy, thio, or silyl, or R1 and R2 in combination form a cycloalkyl or a heterocycle;
- R3 is a substituted or unsubstituted alkyl, acyl, aryl, alkaryl, alkenyl, alkynyl, cycloalkyl, heteroalkyl, heterocycle, sulfinyl, sulfonyl, or silyl;
- X is a leaving group;
- and Y is O, S, SO, or NR10, wherein R10 is a hydrogen, a substituted or unsubstituted alkyl, acyl, aryl, alkaryl, alkenyl, alkynyl, cycloalkyl, heteroalkyl, heterocycle, sulfinyl, sulfonyl, or silyl;
- and
- a second reactant having a diene moiety.
3 more elements
A method of making a 7-membered nitrogen-containing heterocyclic compound via a [4+3] cycloaddition reaction, the method comprising:
- combining a first reactant, a second reactant, and an activator to form a reaction mixture, the first reactant represented by general formula R1R2XC—CO—NHYR3, wherein R1 and R2 are the same or different and are independently selected from hydrogen, halide, a substituted or un-substituted alkyl, acyl, aryl, alkaryl, alkenyl, alkynyl, cycloalkyl, heteroalkyl, heterocycle, amino, amido, alkoxy, acyloxy, thio, or silyl, or R1 and R2 in combination form a cycloalkyl or a heterocycle;
- R3 is a substituted or unsubstituted alkyl, acyl, aryl, alkaryl, alkenyl, alkynyl, cycloalkyl, heteroalkyl, heterocycle, sulfinyl, sulfonyl, or silyl;
- X is a leaving group;
- and Y is O, S, SO, or NR10, wherein R10 is a hydrogen, a substituted or unsubstituted alkyl, acyl, aryl, alkaryl, alkenyl, alkynyl, cycloalkyl, heteroalkyl, heterocycle, sulfinyl, sulfonyl, or silyl;
- the second reactant having a diene moiety;
- and
- reacting the first reactant and the second reactant in the presence of the activator to form the nitrogen-containing heterocyclic compound.
4 more elements
Dependencies are inferred from the claim text.