Hydrazide fixed to a resin and derivatives thereof, and a method for synthesizing pyrazolones in solid phase
AssigneeJapan Science and Technology Corporation
InventorsShu Kobayashi, Hidekazu Oyamada
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Abstract
Hydrazide fixed to a resin represented by the following formula: P—Q—CO—NH—NH2 (I) where P represents a main chain of a resin polymer and Q represents a hydrocarbon side chain optionally having a substituent which may be bonded via a heteroatom, and a hydrazone derived therefrom and fixed to a resin P—Q—CO—NH—N═CH—R1 (II) are provided, and solid phase synthesis of pyrazolone is conducted using the same, thereby enabling synthesis of pyrazolones by the application of the Mannich type reaction based on the solid phase synthesis and efficient construction of libraries for various kinds of them.
Claims3
β-hydrazino ester fixed to a resin represented by the following formula (III):
- where P represents a main chain of a resin polymer, Q represents a hydrocarbon side chain optionally having a substituent which may be boned via a heteroatom, R1, R2, R3 and R4 each represents a hydrocarbon group or a heterocyclic group optionally having a substituent.
A production process for a β-hydrazino ester fixed to a resin as defined in claim 3, wherein the process comprises reacting a hydrazone fixed to a resin represented by the following formula:
- P—Q—CO—NH—N═CH—R1 (II)
- where P represents a main chain of a resin, Q represents a hydrocarbon side chain optionally having a substituent which may be boned via a heteroatom and R1 represents a hydrocarbon group or a heterocyclic group optionally having a substituent, with a ketene silyl acetal represented by the following formula:
- where R2, R3 and R4 each represents a hydrocarbon group or a heterocyclic group which may have a substituent and R6 represents a hydrocarbon group.
A method of synthesizing pyrazolones which comprises reacting a hydrazone fixed to a resin represented by the following formula:
- P—Q—CO—NH—N═CH—R1 (II)
- where P represents a main chain of a resin, Q represents a hydrocarbon side chain optionally having substituent which may be bonded via a heteroatom and R1 represents a hydrocarbon group or a heterocyclic group optionally having a substituent, with ketene silyl acetals represented by the following formula:
- where R2, R3 and R4 each represents a hydrocarbon group or a heterocyclic group which may have a substituent respectively and R6 represents a hydrocarbon group, to synthesize a β-hydrazino ester fixed to a resin represented by the following formula:
- where P, Q, R1, R2, R3 and R4 have the same meanings as described above, which is then cut out from the solid phase and put to cyclizing reaction, to synthesize pyrazolones represented by at least one of the following formulae (A), (B)
- where R1, R2 and R3 have the same meanings as described above.
Dependencies are inferred from the claim text.