Novel compounds or salts thereof, catalysts, methods for preparing novel compounds or salts thereof, and methods for preparing Mannich products.

Abstract

This invention provides novel 1,3-diamine derivatives and their applications. [Solution] The compound is represented by formula (I) or a salt thereof. [Formula 1] TIFF2026519518000105.tif48144

Claims

1. A compound represented by formula (I) or a salt thereof. 【Chemistry 1】 During the ceremony, R １ and R ２ Each of these is independently selected from the group consisting of alkyl, alkenyl, alkynyl, heteroalkyl, heteroalkenyl, or heteroalkynyl, and these may be substituted with one or more substituents selected from the group consisting of aryl and heteroaryl, or R １ and R ２ together form -(CH ２ ) p -, and the -(CH ２ ) p - forms a ring in combination with the nitrogen atom to which both the said R １ and the said R ２ are attached, p is an integer between 2 and 8. The aforementioned - (CH ２ ) p The - may be interrupted by 1 to 3 heteroatoms, and may be substituted with one or more substituents selected from the group consisting of alkyl, aryl, and heteroaryl. R ３ Each of these is independently selected from the group consisting of alkyl and aryl, or Two adjacent R ３ These may form a ring together with the carbon atoms to which they are bonded. R ４ Each of these is independently selected from the group consisting of halogen atoms, alkyl, alkoxy, cyano, nitro, and acylamide, or Two adjacent R ４ These may form a ring together with the carbon atoms to which they are bonded. m is an integer from 0 to 8. n is an integer between 0 and 5.

2. A compound or salt thereof according to claim 1, represented by formula (1-1) or (1-2). 【Chemistry 2】 In the formula, R １ , R ２ , R ３ , R ４ m and n are as defined in claim 1.

3. A catalyst comprising the compound or salt thereof according to claim 1 or claim 2.

4. The catalyst according to claim 3, used in the Mannich reaction.

5. A method for preparing the compound or salt thereof described in claim 1, Converting the -NHMP portion of the compound represented by formula (II) to an amino group, and The carbonyl group of the compound represented by formula (II) is converted to an amino group by reductive amination, and then the introduced amino group is converted to a tertiary amino group -NR １ R ２ This includes forming a part, where R １ and R ２ A method as defined in claim 1. 【Transformation 3】 During the ceremony, PMP is a p-methoxyphenyl group, R ３ , R ４ m and n are as defined in claim 1.

6. A method for preparing a Mannich product, comprising reacting a compound represented by formula (VIII) with a compound represented by formula (VII) in the presence of the compound represented by formula (I) as described in claim 1. 【Chemistry 4】 During the ceremony, R ｃ is either a hydrogen atom or -P(=O)(OR ｄ )(OR ｅ ), -C(=O)R ｄ , -S(=O) ２ R ｄ , -C(=O)OR ｄ Or C(=O)NR ｆ R ｇ A monovalent carbon atom which may be substituted with Here, R ｄ It is an alkyl, R ｅ It is an alkyl, R ｆ is a hydrogen atom or an alkyl group, R ｇ is a hydrogen atom or an alkyl group; 【Transformation 5】 During the ceremony, R ａ Each of these is independently selected from the group consisting of alkyl, halogen atoms, alkoxy, and nitro, or Two adjacent R ａ These may form a ring together with the carbon atoms to which they are bonded. s is an integer between 0 and 4. R ｂ This is a hydrogen atom or an alkoxycarbonyl.

7. A method for preparing the Mannich product according to claim 6, comprising reacting a compound represented by formula (VII) with a compound represented by formula (VII) in the presence of a compound represented by formula (1-1) according to claim 2 to obtain a compound represented by formula (9-1), or reacting them in the presence of a compound represented by formula (1-2) according to claim 2 to obtain a compound represented by formula (9-2). 【Transformation 6】 During the ceremony, R ａ , R ｂ , R ｃ , and s are as defined in claim 6.

8. A method for preparing the Mannich product according to claim 6, comprising reacting a compound represented by formula (VII) with a compound represented by formula (VII') to obtain a compound represented by formula (9-3). 【Transformation 7】 During the ceremony, R ｈ is a hydrogen atom, -P(=O)(OR ｄ ) ( OR ｅ ), -C(=O)R ｄ , -S (=O) ２ R ｄ , -C (=O) OR ｄ , -C(=O)NR ｆ R ｇ , or -P (=O) (OR ｄ ) ( OR ｅ ), -C(=O)R ｄ , -S (=O) ２ R ｄ , -C (=O) OR ｄ Or -C(=O)NR ｆ R ｇ A monovalent hydrocarbon group which may be substituted with Here, R ｄ , R ｅ , R ｆ and R ｇ This is as defined in claim 6; 【Transformation 8】 During the ceremony, R ａ , R ｂ , and s are as defined in claim 6, R ｈ This is as defined above.

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