Efficient Ultrasound-Assisted Approach to N-Benzensulfonyl Phenylacetamide via CuSO4/NaAsc Catalysis in Water and Its Inhibition Activity of Seed Germination

doi:10.6023/cjoc202201010

Abstract

Substituted phenylene and benzenesulfonyl-azides were used as starting materials to obtain N-benzensulfonyl phenylacetamide abscisic mimics (PACs). 32 target compounds were efficiently and quickly obtained via cheap combination of CuSO₄/NaAsc (NaAsc, sodium ascorbate) catalysis under ultrasonic radiation in water (86%~95%). Furthermore, 22 target compounds could overwhelmingly inhibit soybean seed germination at the concentration of 50 and 25 µml/L. These results are benefit to discovering novel seed germination inhibitor agents.

Key words: CuSO₄/NaAsc, ultrasonic radiation, N-benzensulfonyl phenylacetamide, abscisic acid mimics, inhibition seed germination

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Zhiyou Huang, Zhezhi Li, Bo He, Wensheng Li, Ping Yang, Lijun Chen. Efficient Ultrasound-Assisted Approach to N-Benzensulfonyl Phenylacetamide via CuSO₄/NaAsc Catalysis in Water and Its Inhibition Activity of Seed Germination[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1667-1676.

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References 30

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Entry	Catalyst	Solvent	t/min	Yield/%
1	CuSO₄ (0.1 equiv.)/NaAsc (1.0 equiv.)	^tBuOH∶H₂O (V∶V=3∶1)	60	63
2	CuSO₄ (0.1 equiv.)/NaAsc (1.0 equiv.)	^tBuOH∶H₂O (V∶V=2∶1)	60	67
3	CuSO₄ (0.1 equiv.)/NaAsc (1.0 equiv.)	^tBuOH∶H₂O (V∶V=1∶2)	60	71
4	CuSO₄ (0.1 equiv.)/NaAsc (1.0 equiv.)	H₂O	60	83
5	CuSO₄ (0.1 equiv.)/NaAsc (0.5 equiv.)	H₂O	60	83
6	CuSO₄ (0.1 equiv.)/NaAsc (0.4 equiv.)	H₂O	60	83
7	CuSO₄ (0.1 equiv.)/NaAsc (0.3 equiv.)	H₂O	60	78
8	CuSO₄ (0.1 equiv.)/NaAsc (0.1 equiv.)	H₂O	60	46
9	CuSO₄ (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	60	83
10	CuSO₄ (0.02 equiv.)/NaAsc (0.4 equiv.)	H₂O	60	71
11^b	CuSO₄(0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	20	95
12^b	CuSO₄•5H₂O (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	20	95
13^b	Cu(OAc)₂•H₂O (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	20	93
14^b	Cu(OAc)₂ (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	20	93
15^b	CuS (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	20	< 5
16^b	CuI (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	20	45
17^b	Cu(CF₃SO₃)₂ (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	20	91
18^b,c	CuSO₄ (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	13	95
19^b,d	CuSO₄ (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	6	95

Entry	Catalyst	Solvent	t/min	Yield/%
1	CuSO₄ (0.1 equiv.)/NaAsc (1.0 equiv.)	^tBuOH∶H₂O (V∶V=3∶1)	60	63
2	CuSO₄ (0.1 equiv.)/NaAsc (1.0 equiv.)	^tBuOH∶H₂O (V∶V=2∶1)	60	67
3	CuSO₄ (0.1 equiv.)/NaAsc (1.0 equiv.)	^tBuOH∶H₂O (V∶V=1∶2)	60	71
4	CuSO₄ (0.1 equiv.)/NaAsc (1.0 equiv.)	H₂O	60	83
5	CuSO₄ (0.1 equiv.)/NaAsc (0.5 equiv.)	H₂O	60	83
6	CuSO₄ (0.1 equiv.)/NaAsc (0.4 equiv.)	H₂O	60	83
7	CuSO₄ (0.1 equiv.)/NaAsc (0.3 equiv.)	H₂O	60	78
8	CuSO₄ (0.1 equiv.)/NaAsc (0.1 equiv.)	H₂O	60	46
9	CuSO₄ (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	60	83
10	CuSO₄ (0.02 equiv.)/NaAsc (0.4 equiv.)	H₂O	60	71
11^b	CuSO₄(0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	20	95
12^b	CuSO₄•5H₂O (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	20	95
13^b	Cu(OAc)₂•H₂O (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	20	93
14^b	Cu(OAc)₂ (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	20	93
15^b	CuS (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	20	< 5
16^b	CuI (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	20	45
17^b	Cu(CF₃SO₃)₂ (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	20	91
18^b,c	CuSO₄ (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	13	95
19^b,d	CuSO₄ (0.05 equiv.)/NaAsc (0.4 equiv.)	H₂O	6	95

Entry	R¹	R²	3	Yield/%	Entry	R¹	R²	3	Yield/%
1	4-CH₃	H	3a	95	16	H	4-CH₃	3aa	95
2	4-CH₃	4-F	3b	90	17	4-OCH₃	4-CH₃	3ab	93
3	4-CH₃	4-Cl	3c	91	18	4-F	4-CH₃	3ac	92
4	4-CH₃	4-Br	3d	90	19	4-Cl	4-CH₃	3ad	92
5	4-CH₃	4-I	3e	89	20	4-Br	4-CH₃	3ae	91
6	4-CH₃	4-OCF₃	3f	90	21	4-OCF₃	4-CH₃	3af	90
7	4-CH₃	4-CN	3g	86	22	4-COOCH₃	4-CH₃	3ag	88
8	4-CH₃	2-OCH₃	3h	92	23	3-F	4-CH₃	3ah	92
9	4-CH₃	2-F	3i	88	24	3-Cl	4-CH₃	3ai	91
10	4-CH₃	2-Cl	3j	89	25	3-Br	4-CH₃	3aj	92
11	4-CH₃	2-Br	3k	90	26	3-NO₂	4-CH₃	3ak	87
12	4-CH₃	2,4-Cl₂	3l	90	27	2-CH₃	4-CH₃	3al	90
13	4-CH₃	2-Br-4-F	3m	87	28	2-F	4-CH₃	3am	90
14	4-CH₃	3-F-4-OCH₃	3n	91	29	2-Cl	4-CH₃	3an	91
15			3o	88	30	2-Br	4-CH₃	3ao	89
					31	2-CF₃	4-CH₃	3ap	86
					32			3aq	87

Entry	R¹	R²	3	Yield/%	Entry	R¹	R²	3	Yield/%
1	4-CH₃	H	3a	95	16	H	4-CH₃	3aa	95
2	4-CH₃	4-F	3b	90	17	4-OCH₃	4-CH₃	3ab	93
3	4-CH₃	4-Cl	3c	91	18	4-F	4-CH₃	3ac	92
4	4-CH₃	4-Br	3d	90	19	4-Cl	4-CH₃	3ad	92
5	4-CH₃	4-I	3e	89	20	4-Br	4-CH₃	3ae	91
6	4-CH₃	4-OCF₃	3f	90	21	4-OCF₃	4-CH₃	3af	90
7	4-CH₃	4-CN	3g	86	22	4-COOCH₃	4-CH₃	3ag	88
8	4-CH₃	2-OCH₃	3h	92	23	3-F	4-CH₃	3ah	92
9	4-CH₃	2-F	3i	88	24	3-Cl	4-CH₃	3ai	91
10	4-CH₃	2-Cl	3j	89	25	3-Br	4-CH₃	3aj	92
11	4-CH₃	2-Br	3k	90	26	3-NO₂	4-CH₃	3ak	87
12	4-CH₃	2,4-Cl₂	3l	90	27	2-CH₃	4-CH₃	3al	90
13	4-CH₃	2-Br-4-F	3m	87	28	2-F	4-CH₃	3am	90
14	4-CH₃	3-F-4-OCH₃	3n	91	29	2-Cl	4-CH₃	3an	91
15			3o	88	30	2-Br	4-CH₃	3ao	89
					31	2-CF₃	4-CH₃	3ap	86
					32			3aq	87

Compd.	50 μmol•L^–1		25 μmol•L^–1		Compd.	50 μmol•L^–1			25 μmol•L^–1
Compd.	发芽率/%	抑制率/%	发芽率/%	抑制率/%	Compd.	发芽率/%	抑制率/%		发芽率/%	抑制率/%
3a	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	3ac	0.0±0.0	100.0±0.0		0.0±0.0	100.0±0.0
3b	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	3ad	0.0±0.0	100.0±0.0		0.0±0.0	100.0±0.0
3c	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	3ae	0.0±0.0	100.0±0.0		0.0±0.0	100.0±0.0
3d	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	3af	0.0±0.0	100.0±0.0		5.6±1.9	88.9±3.8
3e	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	3ag	0.0±0.0	100.0±0.0		0.0±0.0	100.0±0.0
3f	0.0±0.0	100.0±0.0	4.4±1.9	91.1±3.8	3ah	0.0±0.0	100.0±0.0		0.0±0.0	100.0±0.0
3g	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	3ai	0.0±0.0	100.0±0.0		0.0±0.0	100.0±0.0
3h	0.0±0.0	100.0±0.0	12.2±3.8	75.6±7.7	3aj	0.0±0.0	100.0±0.0		0.0±0.0	100.0±0.0
3i	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	3ak	0.0±0.0	100.0±0.0		0.0±0.0	100.0±0.0
3j	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	3al	0.0±0.0	100.0±0.0		5.6±1.9	88.9±3.8
3k	0.0±0.0	100.0±0.0	12.2±3.8	75.6±7.7	3am	0.0±0.0	100.0±0.0		0.0±0.0	100.0±0.0
3l	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	3an	0.0±0.0	100.0±0.0		0.0±0.0	100.0±0.0
3m	0.0±0.0	100.0±0.0	7.8±1.9	84.4±3.8	3ao	0.0±0.0	100.0±0.0		8.9±1.9	82.2±3.8
3n	0.0±0.0	100.0±0.0	5.6±1.9	88.9±3.8	3ap	0.0±0.0	100.0±0.0		6.7±0.0	86.7±0.0
3o	0.0±0.0	100.0±0.0	4.4±1.9	91.1±3.8	3aq	0.0±0.0	100.0±0.0		6.7±0.0	86.7±0.0
3aa	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	ABA	0.0±0.0	100.0±0.0		6.7±0.0	86.7±0.0
3ab	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	CK			50.0±3.3 (0.5% DMSO)

超声促进CuSO₄/NaAsc水相中高效催化合成N-苯磺酰基苯乙酰胺及其抑制种子萌发的研究

Efficient Ultrasound-Assisted Approach to N-Benzensulfonyl Phenylacetamide via CuSO₄/NaAsc Catalysis in Water and Its Inhibition Activity of Seed Germination

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超声促进CuSO4/NaAsc水相中高效催化合成N-苯磺酰基苯乙酰胺及其抑制种子萌发的研究