Production method for hemiaminal compound and production method for heterocyclic compound

Patent metadata

Field	Value
Publication number	US-12264136-B2
Application number	US-202117480822-A
Country	US
Kind code	B2
Filing date	Sep 21, 2021
Priority date	Mar 28, 2019
Publication date	Apr 1, 2025
Grant date	Apr 1, 2025

Abstract

In a production method for a hemiaminal compound, a compound represented by Formula (1), a compound represented by Formula (2), and an oxidizing agent are mixed. A hemiaminal compound represented by Formula (3) is obtained. In a production method for a heterocyclic compound, a hemiaminal compound is mixed with a base.

First claim

What is claimed is:

1. A production method for a hemiaminal compound, comprising:
mixing a compound represented by Formula (1), a compound represented by Formula (2), and an oxidizing agent to obtain a hemiaminal compound represented by Formula (3),

in the formulae, R 1 represents a hydrocarbon group which may have a substituent,
the hydrocarbon group has 1 to 30 carbon atoms,
the substituent is a group selected from a substituent group W,
the group selected from the substituent group W may be further substituted with a group selected from the substituent group W,
the substituent group W includes a halogen atom, a heteroaryl group, a cyano group, a hydroxyl group, a carboxyl group, a nitro group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic an oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an ammonio group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfamoyl group, an alkyl or arylsulfinyl group, an alkyl or arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an aryl or heterocyclic azo group, an imide group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, a phosphono group, a silyl group, a hydrazino group, an ureido group, and a boronic acid group, and
R 2 and R 3 each independently represent a hydrocarbon group substituted with a halogen atom, a cyano group, a nitro group, an acyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, a dialkylsulfamoyl group, a dialkylamide group, or a heterocyclic group.

2. The production method according to claim 1 ,
wherein R 2 and R 3 each independently represent a fluorinated alkyl group having 1 to 10 carbon atoms.

3. The production method according to claim 1 ,
wherein the compound represented by Formula (1), the compound represented by Formula (2), and the oxidizing agent are mixed in a presence of a halogenated solvent.

4. The production method according to claim 2 ,
wherein the compound represented by Formula (1), the compound represented by Formula (2), and the oxidizing agent are mixed in a presence of a halogenated solvent.

5. The production method according to claim 1 ,
wherein R 1 represents a hydrocarbon group having a leaving group, and
the leaving group is a halogen atom, an alkylsulfonyloxy group which may have a group selected from the substituent group W, an arylsulfonyloxy group which may have a group selected from the substituent group W, an alkylsulfonyl group which may have a group selected from the substituent group W, an arylsulfonyl group which may have a group selected from the substituent group W, a methoxy group, an aryl ester group, or a nitro group.

6. The production method according to claim 2 ,
wherein R 1 represents a hydrocarbon group having a leaving group, and
the leaving group is a halogen atom, an alkylsulfonyloxy group which may have a group selected from the substituent group W, an arylsulfonyloxy group which may have a group selected from the substituent group W, an alkylsulfonyl group which may have a group selected from the substituent group W, an arylsulfonyl group which may have a group selected from the substituent group W, a methoxy group, an aryl ester group, or a nitro group.

7. The production method according to claim 3 ,
wherein R 1 represents a hydrocarbon group having a leaving group, and
the leaving group is a halogen atom, an alkylsulfonyloxy group which may have a group selected from the substituent group W, an arylsulfonyloxy group which may have a group selected from the substituent group W, an alkylsulfonyl group which may have a group selected from the substituent group W, an arylsulfonyl group which may have a group selected from the substituent group W, a methoxy group, an aryl ester group, or a nitro group.

8. The production method according to claim 5 ,
wherein the leaving group is a halogen atom.

9. The production method according to claim 1 ,
wherein the oxidizing agent is selected from the group consisting of an organic nitroxyl radical and an N-hydroxyl form of an organic nitroxyl radical.

10. The production method according to claim 2 ,
wherein the oxidizing agent is selected from the group consisting of an organic nitroxyl radical and an N-hydroxyl form of an organic nitroxyl radical.

11. The production method according to claim 3 ,
wherein the oxidizing agent is selected from the group consisting of an organic nitroxyl radical and an N-hydroxyl form of an organic nitroxyl radical.

12. The production method according to claim 4 ,
wherein the oxidizing agent is selected from the group consisting of an organic nitroxyl radical and an N-hydroxyl form of an organic nitroxyl radical.

13. The production method according to claim 1 ,
wherein the oxidizing agent is selected from the group consisting of a compound represented by Formula (4), a compound represented by Formula (5), and a compound represented by Formula (6),

in the formulae, R 4 represents an oxyradical group or a hydroxyl group, R 5 and R 6 each independently represent a hydrogen atom or a methyl group, and R 7 represents a hydrogen atom, a halogen atom, a hydroxyl group, an acyloxy group, an alkoxy group, an alkoxycarbonyl group, an amino group, an oxo group, a sulfonyloxy group, an N-alkylcarbamoyloxy group, a carboxyl group, a cyano group, an isocyanato group, or an isothiocyanato group.

14. The production method according to claim 13 ,
further comprising mixing a reoxidizing agent.

15. The production method according to claim 14 ,
wherein the reoxidizing agent is a hypervalent iodine compound or an azodicarboxylic acid diester compound.

16. The production method according to claim 14 ,
wherein the reoxidizing agent is a hypervalent iodine compound.

17. The production method according to claim 1 ,
wherein the compound represented by Formula (1) is a compound represented by Formula (7), and
the hemiaminal compound represented by Formula (3) is a hemiaminal compound represented by Formula (8),

in Formulae, R 8 and R 9 each independently represent a hydrogen atom or a hydrocarbon group which may have a substituent, the hydrocarbon group has 1 to 30 carbon atoms, the substituent is a group selected from a substituent group W,

the group selected from the substituent group W may be further substituted with a group selected from the substituent group W,
the substituent group W includes a halogen atom, a heteroaryl group, a cyano group, a hydroxyl group, a carboxyl group, a nitro group, an alkoxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, an ammonio group, an acylamino group, an aminocarbonylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sul

Assignees

• Fujifilm Corp

Inventors

• USHIYAMA Aina

Classifications

• C07C231/12

  by reactions not involving the formation of carboxamide groups · CPC title

• C07C231/08

  from amides by reaction at nitrogen atoms of carboxamide groups · CPC title

• C07D265/06 Primary

  not condensed with other rings · CPC title

• C07C233/47

  having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton · CPC title

• C07C233/22

  having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings · CPC title