Research for the Reaction of Base-Catalyzed Selective Hydrogen- Deuterium Exchange in Mono-1-substituted 1,2,3-Triazoles

doi:10.6023/cjoc202204024

Abstract

An effective and selective deuteration of mono-1-substituted 1,2,3-triazoles using base-catalyzed hydrogen-deuterium exchange is proposed. The H/D exchange was selectively conducted at C5 position of 1,2,3-triazoles with catalytic amount of t-BuOK, t-BuONa or Cs₂CO₃ in dimethyl sulfoxide DMSO-d₆. From corresponding 1,2,3-triazoles via H/D exchange process, 5-deutero and 4-deutero mono-1-substituted 1,2,3-triazoles were given from corresponding 1,2,3-triazoles respectively. In addition, the triazole-induced deuteration on phenyl ring was observed.

Key words: H/D exchange, labeling compounds, mono-1-substituted 1,2,3-triazoles, base-catalysis

Cite this article

Dongying Li, Shanguang Qiu, Yuxue Chen, Yanmei Zhao, Yunlong Wei, Luyong Wu, Wenhao Chen. Research for the Reaction of Base-Catalyzed Selective Hydrogen- Deuterium Exchange in Mono-1-substituted 1,2,3-Triazoles[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2898-2905.

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Entry	Solvent	Base (x equiv.)	Temperature	Time/h	Yield^b/%	D content^c/%
1	DMSO-d₆	Cs₂CO₃ (0.2 equiv.)	80 ℃	6	98	98
2	DMSO-d₆	K₂CO₃ (0.2 equiv.)	80 ℃	6	99	7
3	DMSO-d₆	Cs₂CO₃ (0.2 equiv.)	40 ℃	6	98	71
4	DMSO-d₆	LiO^tBu (0.2 equiv.)	r.t.	6	97	60
5	DMSO-d₆	NaO^tBu (0.2 equiv.)	r.t.	6	99	89
6	DMSO-d₆	NaO^tBu (0.1 equiv.)	r.t.	6	97	97
7	DMSO-d₆	KO^tBu (0.2 equiv.)	r.t.	6	98	98
8	DMSO-d₆	KO^tBu (0.1 equiv.)	r.t.	6	98	97
9	Acetone-d₆	KO^tBu (0.1 equiv.)	r.t.	6	98	0
10	D₂O	KO^tBu (0.1 equiv.)	r.t.	6	99	0
11	CDCl₃	KO^tBu (0.1 equiv.)	r.t.	6	97	0
12	DMSO-d₆	Without	r.t.	6	98	0

Entry	Solvent	Base (x equiv.)	Temperature	Time/h	Yield^b/%	D content^c/%
1	DMSO-d₆	Cs₂CO₃ (0.2 equiv.)	80 ℃	6	98	98
2	DMSO-d₆	K₂CO₃ (0.2 equiv.)	80 ℃	6	99	7
3	DMSO-d₆	Cs₂CO₃ (0.2 equiv.)	40 ℃	6	98	71
4	DMSO-d₆	LiO^tBu (0.2 equiv.)	r.t.	6	97	60
5	DMSO-d₆	NaO^tBu (0.2 equiv.)	r.t.	6	99	89
6	DMSO-d₆	NaO^tBu (0.1 equiv.)	r.t.	6	97	97
7	DMSO-d₆	KO^tBu (0.2 equiv.)	r.t.	6	98	98
8	DMSO-d₆	KO^tBu (0.1 equiv.)	r.t.	6	98	97
9	Acetone-d₆	KO^tBu (0.1 equiv.)	r.t.	6	98	0
10	D₂O	KO^tBu (0.1 equiv.)	r.t.	6	99	0
11	CDCl₃	KO^tBu (0.1 equiv.)	r.t.	6	97	0
12	DMSO-d₆	Without	r.t.	6	98	0

Entry	R	Product	Method	Yield^b/%	D content^c/ %
1	Ph	2a	A, 6 h	96	97
2	p-CH₃C₆H₄	2b	B, 6 h	96	93
3	m-CH₃C₆H₄	2c	A, 6 h	98	96
4	p-CH₃OC₆H₄	2d	B, 12 h	97	98
5	o-CH₃OC₆H₄	2e	B, 8 h	95	100
6	o-EtOC₆H₄	2f	A, 6 h	93	96
7	p-EtOC₆H₄	2g	C, 6 h	95	96
8	p-CNC₆H₄	2h	C, 6 h	95	96
9	m-CNC₆H₄	2i	B, 2.5 h	96	93
10	p-ClC₆H₄	2j	B, 3.5 h	97	99
11	o-ClC₆H₄	2k	A, 6 h	97	70
12	p-BrC₆H₄	2l	C, 6 h	96	96
13	m-BrC₆H₄	2m	B, 4 h	98	99
14	m-CF₃C₆H₄	2n	B, 2.5 h	98	97
15	n-C₉H₁₉	2o	B, 6 h	95	96
16	PhCH₂	2p	B, 6 h	93	100 (α-D: 98)

Entry	R	Product	Method	Yield^b/%	D content^c/ %
1	Ph	2a	A, 6 h	96	97
2	p-CH₃C₆H₄	2b	B, 6 h	96	93
3	m-CH₃C₆H₄	2c	A, 6 h	98	96
4	p-CH₃OC₆H₄	2d	B, 12 h	97	98
5	o-CH₃OC₆H₄	2e	B, 8 h	95	100
6	o-EtOC₆H₄	2f	A, 6 h	93	96
7	p-EtOC₆H₄	2g	C, 6 h	95	96
8	p-CNC₆H₄	2h	C, 6 h	95	96
9	m-CNC₆H₄	2i	B, 2.5 h	96	93
10	p-ClC₆H₄	2j	B, 3.5 h	97	99
11	o-ClC₆H₄	2k	A, 6 h	97	70
12	p-BrC₆H₄	2l	C, 6 h	96	96
13	m-BrC₆H₄	2m	B, 4 h	98	99
14	m-CF₃C₆H₄	2n	B, 2.5 h	98	97
15	n-C₉H₁₉	2o	B, 6 h	95	96
16	PhCH₂	2p	B, 6 h	93	100 (α-D: 98)

碱催化下单-1-取代-1,2,3-三唑选择性氢-氘交换反应研究