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US 2022/0017494 A1Published application
Methods for synthesizing vinylidenes and alkenes
AssigneeThe Board of Trustees of The University of Alabama
InventorsJason Edward Bara, Kathryn Elizabeth O'Harra
Life of this patent
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Abstract
The present disclosure provide synthetic methods for the synthesis of N-substituted vinylidene and alkene compounds in addition to compounds formed from such methods.
Claims20
A method for synthesizing a compound of Formula VI
- the method comprising reacting a compound of Formula II
- with a compound of Formula VII
- or an acetal derivative or a polyacetal derivative thereof, at elevated temperature to form the compound of Formula VI;
- wherein:
- R1 is selected from hydrogen, alkyl, cycloalkyl, heterocycle, aryl, heteroaryl, OR3, SR3, and NR4R5, each of which may be optionally substituted with one or more Z groups;
- R2 is NR6R7;
- R3 is selected from alkyl, cycloalkyl, heterocycle, aryl, and heteroaryl, each of which may be optionally substituted with one or more Z groups;
- R4 and R5 are independently selected from hydrogen, alkyl, cycloalkyl, heterocycle, aryl, and heteroaryl, each of which may be optionally substituted with one or more Z groups;
- or
- R4 and R5 may be brought together with the nitrogen to which they are attached to form a heterocycle ring or a heteroaryl ring, wherein said heterocycle ring or heteroaryl ring may be optionally substituted with one or more Z groups;
- R6 and R7 are independently selected hydrogen, alkyl, cycloalkyl, heterocycle, aryl, and heteroaryl, each of which may be optionally substituted with one or more Z groups;
- or
- R6 and R7 may be brought together with the nitrogen to which they are attached to form a heterocycle ring or a heteroaryl ring, wherein said heterocycle ring or heteroaryl ring may be optionally substituted with one or more Z groups;
- R20 is selected from hydrogen, alkyl, cycloalkyl, heterocycle, aryl, and heteroaryl, each of which may be optionally substituted with one or more Z groups;
- and
- Z is independently selected at each occurrence from alkyl, haloalkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycle, aldehyde, amino, carboxylic acid, ester, ether, halo, hydroxy, keto, nitro, cyano, azido, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, sulfonylamino, and thiol.
13 more elements
A compound of Formula I-a or Formula VI-a:
- wherein:
- X1, X2, X3, X4, X5, and X6 are each selected from N, CH, or C—Z,
- wherein at least one of X1, X2, X3, X4, X5, and X6 is C—Z,
- wherein no more than one of X1, X2, and X3 is N;
- wherein no more than one of X4, X5, and X6 is N;
- R20 is selected from hydrogen, alkyl, cycloalkyl, heterocycle, aryl, and heteroaryl, each of which may be optionally substituted with one or more Z groups;
- and
- Z is independently selected at each occurrence from alkyl, haloalkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycle, aldehyde, amino, carboxylic acid, ester, ether, halo, hydroxy, keto, nitro, cyano, azido, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, sulfonylamino, and thiol.
5 more elements
A compound of Formula III or Formula III-a
- and one or more anions balancing the charge of the compound of Formula III or Formula III-a;
- wherein:
- R10 and R11 are independently selected from alkyl, cycloalkyl, aryl, or heteroaryl, each of which may be optionally substituted with one or more Z groups;
- X1, X2, X3, X4, X5 and X6 are independently selected from N, C—H, or C—Z;
- wherein no more than one of X1, X2, and X3 are N;
- wherein no more than one of X4, X5, and X6 are N;
- R20 is selected from hydrogen, alkyl, cycloalkyl, heterocycle, aryl, and heteroaryl, each of which may be optionally substituted with one or more Z groups;
- and
- Z is independently selected at each occurrence from alkyl, haloalkyl, alkoxy, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycle, aldehyde, amino, carboxylic acid, ester, ether, halo, hydroxy, keto, nitro, cyano, azido, silyl, sulfo-oxo, sulfonyl, sulfone, sulfoxide, sulfonylamino, and thiol.
6 more elements
Dependencies are inferred from the claim text.