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US 2017/0253580 A1Published application
Organic reactions
AssigneeArizona Board of Regents on Behalf of the University of Arizona
InventorsJon T. Njardarson, Isaac Chogii, David Townsend Smith, Edon Vitaku
Life of this patent
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Abstract
The present invention relates to various organic reactions including a method for producing heterocyclic compounds using a [3+2] annulation; a method for producing fluorinated heteroaromatic compounds; and a method for alkylating a meta-position of a phenolic compound.
Claims15
A method for producing a 3-pyrroline compound of the formula:
- said method comprising:
- deprotonating an α,β-unsaturated compound of the formula:
- with a base under condition sufficient to produce a deprotonated intermediate;
- and
- reacting said deprotonated intermediate an imine compound of the formula:
- under conditions sufficient to produce said 3-pyrroline compound,
- wherein
- R is hydrogen, alkyl, haloalkyl, aryl, aralkyl, alkenyl, aralkenyl, cycloalkyl, heteroalkyl, heteroaryl or ester functional group;
- X is a leaving group;
- Y is an auxiliary group;
- and
- Z is an electron withdrawing conjugated group.
9 more elements
A process for producing a fluoroalkyl-substituted heteroaryl compound of the formula:
- comprising
- contacting an aromatic compound of the formula:
- with hexafluoroacetylacetone (Hfacac) under conditions sufficient to produce an intermediate;
- and
- contacting said intermediate with an acid under conditions sufficient to produce a fluoroalkyl-substituted compound of Formula IA,
- wherein
- R is alkyl;
- X is —NRa—, wherein Ra is hydrogen, alkyl or a nitrogen protecting group;
- and
- each of R1, R2 and R3 is independently hydrogen, alkyl, haloalkyl, halide, vinyl, alkynyl, CHO, C(═O)Rb (ketone), CO2Rc (ester), ORd, OSO2Re, aryl and heteroaryl, wherein each of Rb, Rc, Rd, and Re is independently alkyl or aryl.
7 more elements
A process for producing a fluoroalkyl-substituted heteroaryl compound of the formula:
- comprising
- adding hexafluoroacetylacetone (Hfacac) to a solution of phenyliodine diacetate to produce a reactive intermediate solution;
- (ii) adding an aromatic compound of the formula:
- to said reactive intermediate solution under conditions sufficient to produce an intermediate;
- and
- (iii) contacting said intermediate with an acid under conditions sufficient to produce a fluoroalkyl-substituted compound of Formula IA,
- wherein
- R is alkyl;
- X is —NRa—, wherein Ra is hydrogen, alkyl or a nitrogen protecting group;
- and
- each of R1, R2 and R3 is independently hydrogen, alkyl, haloalkyl, halide, vinyl, alkynyl, CHO, C(═O)Rb (ketone), CO2Rc (ester), ORd, OSO2Re, aryl and heteroaryl, wherein each of Rb, Rc, Rd, and Re is independently alkyl or aryl.
8 more elements
15-23. (canceled)
Dependencies are inferred from the claim text.