Direct Assembly of Polysubstituted Benzenes via Base-Catalyzed Benzannulation Reaction of α-Cyano-β-methylalkenyl-(hetero)aryl Ketones

doi:10.6023/cjoc202104056

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (9): 3625-3632.DOI: 10.6023/cjoc202104056 Previous Articles Next Articles

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碱催化α-氰基-β-甲基烯基(杂)芳基酮苯增环反应合成多取代苯

安逸, 张放, 蔡志华, 杜广芬^*()

石河子大学化工学院新疆兵团化工绿色过程重点实验室新疆石河子 832000

收稿日期:2021-04-27 修回日期:2021-06-07 发布日期:2021-06-29
通讯作者: 杜广芬
基金资助:
国家自然科学基金(21662029); 兵团优秀青年教师(2017CB001); 兵团优秀青年教师(CZ027203); 石河子大学国际合作(GJHZ201801)

Direct Assembly of Polysubstituted Benzenes via Base-Catalyzed Benzannulation Reaction of α-Cyano-β-methylalkenyl-(hetero)aryl Ketones

Yi An, Fang Zhang, Zhihua Cai, Guangfen Du()

Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832000

Received:2021-04-27 Revised:2021-06-07 Published:2021-06-29
Contact: Guangfen Du
Supported by:
National Natural Science Foundation of China(21662029); Excellent Young Teachers Plan of Bingtuan(2017CB001); Excellent Young Teachers Plan of Bingtuan(CZ027203); International Cooperation Project of Shihezi University(GJHZ201801)

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Abstract

A mild and transition-metal free method for rapid construction of benzene frameworks has been developed. Under the catalysis of 10 mol% Cs₂CO₃, a variety of α-cyano-β-methylalkenyl(hetero)aryl ketones undergo [4+2] annulation with different dialkyl butynedioates efficiently to produce 1,2-diesteryl-3-(hetero)aryl-4-cyanobenzene derivatives in 62%~94% yields.

Key words: α-cyano-β-methylalkenyl(hetero)aryl ketones, dialkyl butynedioates, [4+2] annulation, 1,2-diesteryl-3-(hetero)- aryl-4-cyanobenzene derivatives

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Yi An, Fang Zhang, Zhihua Cai, Guangfen Du. Direct Assembly of Polysubstituted Benzenes via Base-Catalyzed Benzannulation Reaction of α-Cyano-β-methylalkenyl-(hetero)aryl Ketones[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3625-3632.

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References 13

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Entry	Base	Time/h	Solvent	Yield ^b/%
1	Cs₂CO₃ (20 mol%)	3	CH₃CN	84
2	Na₂CO₃ (20 mol%)	5	CH₃CN	73
3	K₂CO₃ (20 mol%)	5	CH₃CN	80
4	NaOH (20 mol%)	5	CH₃CN	75
5	KOH (20 mol%)	5	CH₃CN	83
6	Et₃N (20 mol%)	4	CH₃CN	72
7	DIPEA (20 mol%)	12	CH₃CN	83
8	DBU (20 mol%)	5	CH₃CN	90
9	AcONa (20 mol%)	36	CH₃CN	85
10	CS₂CO₃ (50 mol%)	3	CH₃CN	77
11	CS₂CO₃ (10 mol%)	3	CH₃CN	94
12	Et₃N (10 mol%)	5	CH₃CN	89
13	DBU (10 mol%)	5	CH₃CN	92
14	Cs₂CO₃ (5 mol%)	5	CH₃CN	75
15	Cs₂CO₃ (10 mol%)	24	Toluene	30
16	Cs₂CO₃ (10 mol%)	5	CH₂Cl₂	70
17	Cs₂CO₃ (10 mol%)	3	ClCH₂CH₂Cl	70
18	Cs₂CO₃ (10 mol%)	4	1,4-Dioxane	78
19^c	Cs₂CO₃ (10 mol%))	3	CH₃CN	93
20	No base	24	CH₃CN	0

Entry	Base	Time/h	Solvent	Yield ^b/%
1	Cs₂CO₃ (20 mol%)	3	CH₃CN	84
2	Na₂CO₃ (20 mol%)	5	CH₃CN	73
3	K₂CO₃ (20 mol%)	5	CH₃CN	80
4	NaOH (20 mol%)	5	CH₃CN	75
5	KOH (20 mol%)	5	CH₃CN	83
6	Et₃N (20 mol%)	4	CH₃CN	72
7	DIPEA (20 mol%)	12	CH₃CN	83
8	DBU (20 mol%)	5	CH₃CN	90
9	AcONa (20 mol%)	36	CH₃CN	85
10	CS₂CO₃ (50 mol%)	3	CH₃CN	77
11	CS₂CO₃ (10 mol%)	3	CH₃CN	94
12	Et₃N (10 mol%)	5	CH₃CN	89
13	DBU (10 mol%)	5	CH₃CN	92
14	Cs₂CO₃ (5 mol%)	5	CH₃CN	75
15	Cs₂CO₃ (10 mol%)	24	Toluene	30
16	Cs₂CO₃ (10 mol%)	5	CH₂Cl₂	70
17	Cs₂CO₃ (10 mol%)	3	ClCH₂CH₂Cl	70
18	Cs₂CO₃ (10 mol%)	4	1,4-Dioxane	78
19^c	Cs₂CO₃ (10 mol%))	3	CH₃CN	93
20	No base	24	CH₃CN	0

Entry	Ketone	Product	3, Yield^b/% of 3
1			3a, 94 (92)^c
2			3b, 75
3			3c, 91
4			3d, 89
5			3e, 90
6			3f, 84
7			3g, 90
8			3h, 75
Entry	Ketone	Product	3, Yield^b/% of 3
9			3i, 89
10			3j, 82
11			3k, 73
12			3l, 81
13			3m, 80
14			3n, 75
15			3o, 72
16			3p, 87
17			3q, 80
Entry	Ketone	Product	3, Yield^b/% of 3
18			3r, 81
19			3s, 92
20			3t, 90
21^d		—	ND
22		—	ND
23		—	ND
24		—	ND

Entry	Ketone	Product	3, Yield^b/% of 3
1			3a, 94 (92)^c
2			3b, 75
3			3c, 91
4			3d, 89
5			3e, 90
6			3f, 84
7			3g, 90
8			3h, 75
Entry	Ketone	Product	3, Yield^b/% of 3
9			3i, 89
10			3j, 82
11			3k, 73
12			3l, 81
13			3m, 80
14			3n, 75
15			3o, 72
16			3p, 87
17			3q, 80
Entry	Ketone	Product	3, Yield^b/% of 3
18			3r, 81
19			3s, 92
20			3t, 90
21^d		—	ND
22		—	ND
23		—	ND
24		—	ND

碱催化α-氰基-β-甲基烯基(杂)芳基酮苯增环反应合成多取代苯

Direct Assembly of Polysubstituted Benzenes via Base-Catalyzed Benzannulation Reaction of α-Cyano-β-methylalkenyl-(hetero)aryl Ketones

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