Synthesis of 2-Substituted Cyclopenta[c]chromene Derivatives by α-C Insertion of Acetonitrile (Acetone)

doi:10.6023/cjoc202107043

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (1): 181-189.DOI: 10.6023/cjoc202107043 Previous Articles Next Articles

ARTICLES

乙腈(丙酮)α-C嵌入合成2-取代环戊烯并[c]色烯衍生物

钱宇亮, 许岚, 童义涵, 刘天怿, 夏盈盈, 胡顶茂, 荣良策^*()

江苏师范大学化学与材料科学学院江苏徐州 221116

收稿日期:2021-07-19 修回日期:2021-09-05 发布日期:2021-09-14
通讯作者: 荣良策
基金资助:
江苏省高校自然科学研究项目(18KJA150004); 大学生创新创业训练计划和江苏省高校品牌专业建设工程资助项目

Synthesis of 2-Substituted Cyclopenta[c]chromene Derivatives by α-C Insertion of Acetonitrile (Acetone)

Yuliang Qian, Lan Xu, Yihan Tong, Tianyi Liu, Yingying Xia, Dingmao Hu, Liangce Rong()

School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116

Received:2021-07-19 Revised:2021-09-05 Published:2021-09-14
Contact: Liangce Rong
Supported by:
Natural Science Foundation of the Jiangsu Higher Education Institutions(18KJA150004); Undergraduate Innovation and Entrepreneurship Training Program, and the Brand Major of Universities in Jiangsu Province

1. .pdf(2891KB)

Abstract

The efficient synthesis of 2-substituted cyclopenta[c]chromene derivatives was realized by α-C insertion of acetonitrile (acetone) with oxygen-linked 1,7-enynes catalyzed by cuprous bromide. The advantages of this reaction were wide range of substrates, high compatiblity of functional groups and good yield. The results showed that this was a radical reaction process, and it was also an effective way to construct oxygen-containing heterocycles. The X-ray diffraction analysis of 1-(4-fluorophenyl)-3a,8-dimethyl-2,3,3a,4-tetrahydrocyclopenta[c]chromene-2-carbonitrile (3am) further confirmed the structure of the product.

Key words: radical reaction, oxygen-linked 1,7-enyne, chromene, CuBr

Cite this article

Yuliang Qian, Lan Xu, Yihan Tong, Tianyi Liu, Yingying Xia, Dingmao Hu, Liangce Rong. Synthesis of 2-Substituted Cyclopenta[c]chromene Derivatives by α-C Insertion of Acetonitrile (Acetone)[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 181-189.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 4

References 21

[1]	Shi, Y.; Zhou, C.-H. Biomed. Chem. Lett. 2011, 21, 956. doi: 10.1016/j.bmcl.2010.12.059
[2]	Yang, G.-Y.; Wang, C.-X.; Huang, L.-T.; Xu, C.-L. Chin. J. Synth. Chem. 2011, 9, 337. (in Chinese)
	(杨国玉, 王彩霞, 黄立挺, 徐翠莲, 合成化学, 2011, 9, 337.)
[3]	Abdizadeh, T.; Kalani, M. R.; Abnous, K.; Tayarani, Z.; Khashyarmanesh, B. Z.; Abdizadeh, R.; Ghodsi, R.; Hadizadeh, F. Eur. J. Med. Chem. 2017, 132, 42. doi: S0223-5234(17)30180-0 pmid: 28340413
[4]	Daly, A. K. Arch. Toxicol. 2013, 87, 407. doi: 10.1007/s00204-013-1013-9 pmid: 23376975
[5]	Kirkiacharian, S.; Thuy, D. T.; Sicsic, S. Farmaco 2002, 57, 703. pmid: 12385519
[6]	Zhang, M.; Wang, N.; Xu, W.; Huang, Z.; Shi, D. Chin. J. Org. Chem. 2019, 39, 1085. (in Chinese)
	(张梦烨, 王宁, 徐文韬, 黄志斌, 史达清, 有机化学, 2019, 39, 1085.) doi: 10.6023/cjoc201809042
[7]	(a) Zheng, Y.-X.; Xun, Z.; Zhang, J.-J.; Huang, Z.-B.; Shi, D.-Q. Mol. Diversity 2017, 21, 293. doi: 10.1007/s11030-016-9723-6
	(b) Lin, W.; Zheng, Y.; Wang, Y.; Shi, D. Heterocycles 2016, 92, 2235. doi: 10.3987/COM-16-13567
	(c) Jin, P.-P.; Liu, X.-C.; Liu, D.-Q.; Huang, Z.-B.; Shi, D.-Q. J. Heterocycl. Chem. 2015, 52, 1625. doi: 10.1002/jhet.v52.6
[8]	Bai, Q.; He, J.; Zhu, X.; Feng, G.; Jin, C. Chin. J. Org. Chem. 2019, 39, 527. (in Chinese) doi: 10.6023/cjoc201807058
	(白其凡, 何静耀, 祝小青, 冯高峰, 金城安, 有机化学, 2019, 39, 527.) doi: 10.6023/cjoc201807058
[9]	Sun, W.; Mao, Y.; Jiang, J.; Yu, J.; Chen, L.; Hu, Y.; Zhang, S. Chin. J. Org. Chem. 2019, 39, 2525. (in Chinese) doi: 10.6023/cjoc201903034
	(孙婉婉, 毛玉键, 蒋静, 余靓, 陈凌云, 胡延维, 张士磊, 有机化学, 2019, 39, 2525.) doi: 10.6023/cjoc201903034
[10]	Wang, X.; Chen, P.; Zhi, S.; Hu, H.; Kan, Y.; Zhang, Z. Chin. J. Org. Chem. 2019, 39, 3299. (in Chinese) doi: 10.6023/cjoc201903032
	(王翔, 陈平, 支三军, 胡华友, 阚玉和, 张载超, 有机化学, 2019, 39, 3299.) doi: 10.6023/cjoc201903032
[11]	Yue, Y.; Xie, Z.; Chu, Y.; Xue, S. Chin. J. Org. Chem. 2020, 40, 501. (in Chinese) doi: 10.6023/cjoc201907033
	(岳永双, 解正峰, 褚义成, 薛松松, 有机化学, 2020, 40, 501.) doi: 10.6023/cjoc201907033
[12]	Chen, W.; Yuan, R.; Fang, Y.; Dong, H.; Yasen, B.; Su, L.; Ren, X.; Zhou, H.; Wan, Y.; Zhang, P.; Zhou, S.; Wu, H. Chin. J. Org. Chem. 2020, 40, 988. (in Chinese) doi: 10.6023/cjoc201908029
	(陈雯, 苑睿, 房越, 董宏瑞, 布麦热叶木•亚生, 苏柳娟, 任璇璇, 周杭, 宛瑜张鹏周生亮, 有机化学, 2020, 40, 988.) doi: 10.6023/cjoc201908029
[13]	Zang, W.; Wei, Y.; Shi, M. Chem. Commun. 2019, 55, 8126. doi: 10.1039/C9CC03735G
[14]	Chen, J.; Han, X.; Lu, X. Org. Lett. 2019, 21, 8153. doi: 10.1021/acs.orglett.9b02412
[15]	(a) Gu, Y.; Dai, L.; Mao, K.; Zhang, J.; Wang, C.; Zhao, L.; Rong, L. Org. Lett. 2020, 22, 2956. doi: 10.1021/acs.orglett.0c00682
	(b) Gu, Y.; Dai, L.; Zhang, J.; Lu, X.; Liu, X.; Wang, C.; Zhang, J.; Rong, L. J. Org. Chem. 2021, 86, 2173. doi: 10.1021/acs.joc.0c02275
[16]	Qiu, J.-K.; Jiang, B.; Zhu, Y.-L.; Hao, W.-J.; Wang, D.-C.; Sun, J.; Wei, P.; Tu, S.-J.; Li, G. J. Am. Chem. Soc. 2015, 137, 8928. doi: 10.1021/jacs.5b05735 pmid: 26131954
[17]	Wu, C.; Liao, J.; Ge, S. Angew. Chem., Int. Ed. 2019, 58, 8882. doi: 10.1002/anie.v58.26
[18]	Sun, K.; Si, Y.-F.; Chen, X.-L.; Lv, Q.-Y.; Jiang, N.; Wang, S.-S.; Peng, Y.-Y.; Qu, L.-B.; Yu, B. Adv. Synth. Cata. 2019, 361, 4483.
[19]	Liu, Q.; Mei, Y.; Wang, L.; Ma, Y.; Li, P. Adv. Synth. Catal. 2020, 362, 5669. doi: 10.1002/adsc.v362.24
[20]	Hu, M.; Li, M.; Tan, F.-L.; Song, R.-J.; Xie, Y.-X.; Li, J.-H. Adv. Synth. Catal. 2017, 359, 120. doi: 10.1002/adsc.v359.1
[21]	(a) Mao, K.; Bian, M.; Dai, L.; Zhang, J.; Yu, Q.; Wang, C.; Rong, L. Org. Lett. 2021, 23, 218. doi: 10.1021/acs.orglett.0c03946
	(b) Mao, K.; Dai, L.; Chen, A.; Liu, Y.; Liu, X.; Wang, C.; Rong, L. Asian J. Org. Chem. 2021, 10, 851. doi: 10.1002/ajoc.v10.4

乙腈(丙酮)α-C嵌入合成2-取代环戊烯并[c]色烯衍生物

Synthesis of 2-Substituted Cyclopenta[c]chromene Derivatives by α-C Insertion of Acetonitrile (Acetone)

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 4

References 21

Related Articles 15

Recommended Articles

Metrics

Comments

Entry	Cat.	Oxidant	Temp./℃	Time/h	Yield^b/%
1	CuCl	DTBP	120	8	60
2	Cu₂O	DTBP	120	8	59
3	CuBr	DTBP	120	8	65 (dr>20∶1)
4	CuI	DTBP	120	8	45
5	CuCl₂	DTBP	120	8	51
6	Cu(OAc)₂	DTBP	120	8	48
7	Cu(OTf)₂	DTBP	120	8	37
8	CuBr	BPO	120	8	43 (dr>20∶1)
9	CuBr	TBPB	120	8	51 (dr>20∶1)
10	CuBr	K₂S₂O₈	120	8	36 (dr>20∶1)
11	CuBr	DTBP	120	10	70 (dr>20∶1)
12	CuBr	DTBP	120	12	74 (dr>20∶1)
13	CuBr	DTBP	120	14	73 (dr>20∶1)
14	CuBr	DTBP	130	12	70 (dr>20∶1)
15	CuBr	DTBP	140	12	65 (dr>20∶1)
16	CuBr	DTBP	100	12	42 (dr>20∶1)
17	CuBr	DTBP	90	12	30 (dr>20∶1)
18^c	CuBr	DTBP	120	12	45 (dr>20∶1)
19^d	CuBr	DTBP	120	12	53 (dr>20∶1)
20^e	CuBr	DTBP	120	12	41 (dr>20∶1)
21	—	DTBP	120	12	10
22	CuBr	—	120	12	0

[1]	Fen Huang, Weiwei Luo, Jun Zhou. Research Progress of Polychloroalkylation Based on C—H Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2368-2390.
[2]	Jinxiao Zhao, Tonghui Wei, Sen Ke, Yi Li. Visible Light-Catalyzed Synthesis of Difluoroalkylated Polycyclic Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1102-1114.
[3]	Zhaoming Hu, Jihong Wu, Jingjing Wu, Fanhong Wu. Research Progress on Direct Trifluoromethylselenylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 36-56.
[4]	Jiling Yi, Kangqi Shi, Binglin Wu, Wanshan Li, Guangying Chen. Study on Secondary Metabolites of Marine-Derived Fungus Eutypella sp. F0219 [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 295-298.
[5]	Shiwei Yu, Zhaohua Chen, Qi Chen, Shuting Lin, Jinping He, Guanshen Tao, Zhaoyang Wang. Research Progress in Synthesis and Application of Thiosulfonates [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2322-2330.
[6]	Lizhi Zhang, Yongjian Liao, Ning Chen, Lei Huang, Min Zhou. Cyclization and Coupling Reactions Promoted by Potassium tert-Butoxide [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1950-1959.
[7]	Yadong Li, Pengju Wu, Zhiyong Yang. Synthesis of 2-Aryl Benzoxazoles from Benzoxazoles and α-Ketoic Acids by Photoredox Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1770-1777.
[8]	Baitong Yue, Xinxin Wu, Chen Zhu. Recent Advances in Vinyl Radical-Mediated Hydrogen Atom Transfer [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 458-470.
[9]	Yamin Sun, Xiyong Li, Jinwei Yuan, Jialin Yu, Shuainan Liu. CuI-Catalyzed Regioselective Synthesis of 3-Arylcoumarins with Arylamines under Mild Conditions [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 631-640.
[10]	Yaohui Xu, Zhen Wu, Xinxin Wu, Chen Zhu. Transition-Metal Free Radical-Mediated C—H Bond Alkynylation and Allylation of Ethers, Aldehydes and Amides [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4340-4349.
[11]	Pan-Pan Gao, Wen-Jing Xiao, Jia-Rong Chen. Recent Progresses in Visible-Light-Driven Alkene Synthesis [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 3923-3943.
[12]	Mengqi Zhang, Guangming Nan, Xiaohui Zhao, Wei Wei. Visible-Light-Mediated C3-H Acetalation of Quinoxalin-2(1H)-ones [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4315-4322.
[13]	Hao Xu, Jie Zhang, Junze Zuo, Fengxiao Wang, Jian Lü, Xu Hun, Daoshan Yang. Recent Advances in Visible-Light-Catalyzed C—C Bonds and C—Heteroatom Bonds Formation Using Sulfonium Salts [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4037-4059.
[14]	Qian Xiao, Qing-Xiao Tong, Jian-Ji Zhong. Recent Progress on the Synthesis of Benzazepine Derivatives via Radical Cascade Cyclization Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 3979-3994.
[15]	Yechun Wu, Jintao Yu. Recent Advances in the Decarboxylative Acylation/Cyclization of α-Keto Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3606-3619.