Synthesis of 9-Cyanoanthracene Derivatives by Tandem Reaction of Aryne with ortho-Arylformylphenylacetonitrile

doi:10.6023/cjoc202503005

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (10): 3816-3823.DOI: 10.6023/cjoc202503005 Previous Articles Next Articles

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苯炔与邻芳基甲酰苯乙腈串联反应合成9-氰基蒽衍生物

李双俊, 龚潩, 张放, 杜广芬, 何林^*()

石河子大学化学化工学院新疆石河子 832000

收稿日期:2025-03-06 修回日期:2025-05-11 发布日期:2025-06-11
基金资助:
新疆天山研究项目(2023TSYCCX0122); 石河子大学国际合作项目(GJHZ202204); 石河子大学引导(2022ZD021); 石河子大学引导(2022ZD067)

Synthesis of 9-Cyanoanthracene Derivatives by Tandem Reaction of Aryne with ortho-Arylformylphenylacetonitrile

Shuangjun Li, Yi Gong, Fang Zhang, Guangfen Du, Lin He^*()

School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832000

Received:2025-03-06 Revised:2025-05-11 Published:2025-06-11
Contact: * helin@shzu.edu.cn
Supported by:
Tianshan Talent Research Project of Xinjiang(2023TSYCCX0122); International Cooperation Project of Shihezi University (No. GJHZ202204, and the Guidance Project of Shihezi University(2022ZD021); International Cooperation Project of Shihezi University (No. GJHZ202204, and the Guidance Project of Shihezi University(2022ZD067)

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Abstract

A new method for constructing 9-cyanoanthracene compounds by reacting aryne with ortho-arylformylphenyl-acetonitrile under mild conditions was introduced. Using 2-(trimethylsilicone)phenyltrifluoromethanesulfonate as the aryne precursor, KF/18-C-6 as the fluorine source, and ^tBuONa as the base, the aryne in situ generated can undergo a tandem cyclization/aromatization reaction triggered by carbon nucleophilic attack with ortho-arylformylphenylacetonitrile, and 20 differently substituted 9-cyanoanthracene products were synthesized in 47%~95% yields.

Key words: aryne, ortho-arylformylphenylacetonitrile, 9-cyanoanthracene

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Shuangjun Li, Yi Gong, Fang Zhang, Guangfen Du, Lin He. Synthesis of 9-Cyanoanthracene Derivatives by Tandem Reaction of Aryne with ortho-Arylformylphenylacetonitrile[J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3816-3823.

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References 23

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Entry	Fluoride source	Base	Additive	Solvent	Yield^b/%
1	KF/18-C-6			THF	16
2	KF/18-C-6	Cs₂CO₃		THF	34
3	CsF	Cs₂CO₃		THF	12
4	CsF/18-C-6	Cs₂CO₃		THF	17
5	TBAF•3H₂O	Cs₂CO₃		THF	44
6	TMAF•4H₂O	Cs₂CO₃		THF	40
7	TBAF•3H₂O	Cs₂CO₃	4 Å MS	THF	65
8	TMAF•4H₂O	Cs₂CO₃	4 Å MS	THF	58
9	KF/18-C-6	Cs₂CO₃	4 Å MS	THF	69
10	KF/18-C-6	K₂CO₃	4 Å MS	THF	41
11	KF/18-C-6	^tBuOK	4 Å MS	THF	68
12	KF/18-C-6	^tBuONa	4 Å MS	THF	88
13	KF/18-C-6	^tBuONa	4 Å MS	DME	47
14	KF/18-C-6	^tBuONa	4 Å MS	Toluene	59
15	KF/18-C-6	^tBuONa	4 Å MS	DCM	21
16	KF/18-C-6	^tBuONa	4 Å MS	CH₃CN	28
17^c	KF/18-C-6	^tBuONa	4 Å MS	THF	53
18^d	KF/18-C-6	^tBuONa	4 Å MS	THF	40
19^e	KF/18-C-6	^tBuONa	4 Å MS	THF	50
20^f	KF/18-C-6	^tBuONa	4 Å MS	THF	61
21^g	KF/18-C-6	^tBuONa	4 Å MS	THF	64
22^h	KF/18-C-6	^tBuONa	4 Å MS	THF	49
23ⁱ	KF/18-C-6	^tBuONa	4 Å MS	THF	36

Entry	Fluoride source	Base	Additive	Solvent	Yield^b/%
1	KF/18-C-6			THF	16
2	KF/18-C-6	Cs₂CO₃		THF	34
3	CsF	Cs₂CO₃		THF	12
4	CsF/18-C-6	Cs₂CO₃		THF	17
5	TBAF•3H₂O	Cs₂CO₃		THF	44
6	TMAF•4H₂O	Cs₂CO₃		THF	40
7	TBAF•3H₂O	Cs₂CO₃	4 Å MS	THF	65
8	TMAF•4H₂O	Cs₂CO₃	4 Å MS	THF	58
9	KF/18-C-6	Cs₂CO₃	4 Å MS	THF	69
10	KF/18-C-6	K₂CO₃	4 Å MS	THF	41
11	KF/18-C-6	^tBuOK	4 Å MS	THF	68
12	KF/18-C-6	^tBuONa	4 Å MS	THF	88
13	KF/18-C-6	^tBuONa	4 Å MS	DME	47
14	KF/18-C-6	^tBuONa	4 Å MS	Toluene	59
15	KF/18-C-6	^tBuONa	4 Å MS	DCM	21
16	KF/18-C-6	^tBuONa	4 Å MS	CH₃CN	28
17^c	KF/18-C-6	^tBuONa	4 Å MS	THF	53
18^d	KF/18-C-6	^tBuONa	4 Å MS	THF	40
19^e	KF/18-C-6	^tBuONa	4 Å MS	THF	50
20^f	KF/18-C-6	^tBuONa	4 Å MS	THF	61
21^g	KF/18-C-6	^tBuONa	4 Å MS	THF	64
22^h	KF/18-C-6	^tBuONa	4 Å MS	THF	49
23ⁱ	KF/18-C-6	^tBuONa	4 Å MS	THF	36

苯炔与邻芳基甲酰苯乙腈串联反应合成9-氰基蒽衍生物

Synthesis of 9-Cyanoanthracene Derivatives by Tandem Reaction of Aryne with ortho-Arylformylphenylacetonitrile

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