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US 12,662,499 B2Granted
Phosphorus compounds and methods thereof
AssigneeAgency for Science, Technology and Research
InventorsMartin Van Meurs, James David Nobbs, Sigit Sugiarto
Life of this patent
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Abstract
The disclosure concerns phosphorus compounds of formula (I), (II) and (III) and methods of synthesising these compounds. The phosphorus compound can be a cyclic phosphorus compound. The method comprises reacting a compound having two Michael acceptor groups with a hypophosphite ester, acid, salt or solvate thereof and an optional organosilicon compound. The diene can be a cyclodiene.
Claims17
A method of synthesising a phosphorus compound of Formula (I), a salt, solvate or isomer thereof:
- wherein Y is selected from an optionally substituted C1-10 alkylene, optionally substituted C1-10 alkenylene, optionally substituted silylene, optionally substituted aminoylene, acylene, thioacylene, sulfinylene, sulfonylene, —P(O)(OZ)— or —P+(R9R10)—;
- Z is selected from H, optionally substituted alkyl or a metal cation;
- R1, R2, R7 and R8 are independently selected from oxo, halo, optionally substituted alkyl;
- optionally substituted alkenyl;
- optionally substituted haloalkyl;
- optionally substituted alkynyl;
- optionally substituted oxyalkyl;
- optionally substituted amino, optionally substituted thio, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted heterocyclyl, optionally substituted heteroaryl, and optionally substituted aryl;
- wherein R1 and R5 can be linked to form an optionally substituted cycloalkyl;
- R3, R4, R5, and R6 are independently selected from H, oxo, halo, optionally substituted alkyl;
- optionally substituted alkenyl;
- optionally substituted haloalkyl;
- optionally substituted alkynyl;
- optionally substituted oxyalkyl;
- optionally substituted amino, optionally substituted thio, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted heterocyclyl, optionally substituted heteroaryl, and optionally substituted aryl;
- R9 and R10 are independently selected from H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted heterocycloyl, optionally substituted aryl, optionally substituted heteroaryl;
- the method comprising:
- a) reacting a compound of Formula (A) with a hypophosphite ester, acid, salt or solvate thereof and an optional organosilicon compound, the compound of Formula (A) is
- wherein Y is selected from an optionally substituted C1-10 alkylene, optionally substituted C1-10 alkenylene, optionally substituted silylene, optionally substituted amino, acylene, thioacylene, sulfinylene, sulfonylene, —P(O)(OZ)— or —P+(R13R14)—;
- wherein R1, R2, R7 and R8 are independently selected from oxo, halo, optionally substituted alkyl;
- optionally substituted alkenyl;
- optionally substituted haloalkyl;
- optionally substituted alkynyl;
- optionally substituted oxyalkyl;
- optionally substituted amino, optionally substituted thio, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted heterocyclyl, optionally substituted heteroaryl, and optionally substituted aryl;
- wherein R1 and R8 can be linked to form an optionally substituted cyclo moiety;
- R3 and R5 are independently selected from H, oxo, halo, optionally substituted alkyl;
- optionally substituted alkenyl;
- optionally substituted haloalkyl;
- optionally substituted alkynyl;
- optionally substituted oxyalkyl;
- optionally substituted amino, optionally substituted thio, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted heterocyclyl, optionally substituted heteroaryl, and optionally substituted aryl;
- and
- wherein R13 and R14 are independently selected from H, optionally substituted C1-C10 alkyl, optionally substituted C3-C10 cycloalkyl, optionally substituted C3-C10 heterocyclyl, optionally substituted aryl, or optionally substituted heteroaryl.
31 more elements
Dependencies are inferred from the claim text.