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US 11,873,315 B2Granted
Chiral n-heterocyclic phosphorodiamidic acids (NHPAS) and derivatives as novel Brønsted acid catalysts
AssigneeThe Board of Regents of the Nevada System of Higher Education On Behalf of the University of Nevada, Las Vegas
InventorsJun Yong Kang, Hai Huang
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Abstract
Provided herein are diaryl and arylalkyl phosphonates, useful as intermediates in, for example, the synthesis of leukocyte elastase inhibitors, potassium channel modulators, chemiluminescence materials, and flame retardants, and methods for making same. Also provided are N-heterocyclic phosphorodiamidic acids (NHPAs) useful in reactions such as, for example, in the preparation of diaryl and arylalkyl phosphonates. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
Claims9
A compound having a structure represented by a formula:
- wherein n is selected from 0 and 1;
- wherein R101a is —OH;
- wherein R101b is independently selected from hydrogen, halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino, provided that at least one of R101a and R101b is —OH, —SH, or C1-C4 alkylamino;
- wherein each of R102a, R102b, and R102c is independently selected from hydrogen, halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino;
- wherein R103 is selected from C4-C8 alkyl and Ar101, provided that when R103 is C4-C8 alkyl, then R101b is —SH, —OH, or C1-C4 alkylamino;
- wherein Ar101, when present, is selected from C6-C10 aryl and C5-C6 heteroaryl, and is substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and phenyl;
- wherein R104 is selected from C1-C4 alkoxy and phenyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino;
- and
- wherein R105 is C1-C4 alkyl,
- provided that when n is 0, R101b is —OH, and R103 is C6 aryl or C6 heteroaryl, then either:
- (a) each of R102a and R102b is hydrogen, or
- (b) one of R102a and R102b is hydrogen and R104 is not the same as —OR5,
- or a pharmaceutically acceptable salt thereof.
10 more elements
A compound selected from:
A compound having a structure represented by a formula:
- wherein n is selected from 0 and 1;
- wherein each of R101a and R101b is independently selected from hydrogen, halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino, provided that at least one of R101a and R101b is —OH, —SH, or C1-C4 alkylamino;
- wherein each of R102a, R102b, and R102C is independently selected from hydrogen, halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino;
- wherein R103 is selected from C4-C8 alkyl and Ar101, provided that when R103 is C4-C8 alkyl, then either
- (a) at least one of R101a and R101b is —SH or C1-C4 alkylamino, or
- (b) R101b is —OH;
- wherein Ar101, when present, is selected from C6-C10 aryl and C5-C6 heteroaryl, and is substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and phenyl;
- wherein R104 is unsubstituted phenyl;
- and
- wherein R105 is C1-C4 alkyl,
- provided that when n is 0, R101b is —OH, and R103 is C6 aryl or C6 heteroaryl, then either:
- (c) each of R102a and R102b is hydrogen, or
- (d) one of R102a and R102b is hydrogen,
- or a pharmaceutically acceptable salt thereof.
11 more elements
Dependencies are inferred from the claim text.