1,4-Diazabicyclo[2.2.2]octane (DABCO)-Catalyzed [4+2] Domino Reaction of Allenoates: Synthesis of Benzo[4,5]thieno-[3,2-b]pyran Derivatives

doi:10.6023/cjoc201904082

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (8): 2175-2182.DOI: 10.6023/cjoc201904082 Previous Articles Next Articles

Special Issue: 陈茹玉先生诞辰100周年

Articles

1,4-二氮杂二环[2.2.2]辛烷(DABCO)催化联烯的[4+2]串联反应:合成苯并噻吩并吡喃衍生物

贾继茹, 于爱敏, 刘旭光, 孟祥太

天津市有机太阳能电池与光化学转换重点实验室天津理工大学化学化工学院天津 300384

收稿日期:2019-04-30 修回日期:2019-06-25 发布日期:2019-07-09
通讯作者: 孟祥太 E-mail:xtmeng@tjut.edu.cn
基金资助:
国家自然科学基金（No.21403154）、天津市自然科学基金（No.17JCZDJC37700）、天津市教育委（No.20180KJ137）资助项目.

1,4-Diazabicyclo[2.2.2]octane (DABCO)-Catalyzed [4+2] Domino Reaction of Allenoates: Synthesis of Benzo[4,5]thieno-[3,2-b]pyran Derivatives

Jia Jiru, Yu Aimin, Liu Xuguang, Meng Xiangtai

Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin 300384 China

Received:2019-04-30 Revised:2019-06-25 Published:2019-07-09
Contact: 10.6023/cjoc201904082 E-mail:xtmeng@tjut.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21403154), the Natural Science Foundation of Tianjin City (No. 17JCZDJC37700) and the Tianjin Municipal Education Commission (No. 20180KJ137).

1. 1,4-Diazabicyclo[2.2.2]octane (DABCO)-Catalyzed [4+2] Domino Reaction of Allenoates: Synthesis of Benzo[4,5]thieno-[3,2-b]pyran Derivatives.PDF(2703KB)

Abstract

A 1,4-diazabicyclo[2.2.2]octane (DABCO)-catalyzed[4+2] annulation reaction between 2-alkylidenebenzothio phene-3(2H)-ones and allenoate has been developed. The substrate scope includes both electron-withdrawing and electron-donating groups on the benzothiophene moiety. This method can be carried out under mild conditions and gives a wide range of highly functionalized benzothiophene-fused γ-pyran derivatives in good yields with moderate selectivity.

Key words: domino reaction, allenoate, benzothiophene derivatives

Cite this article

Jia Jiru, Yu Aimin, Liu Xuguang, Meng Xiangtai. 1,4-Diazabicyclo[2.2.2]octane (DABCO)-Catalyzed [4+2] Domino Reaction of Allenoates: Synthesis of Benzo[4,5]thieno-[3,2-b]pyran Derivatives[J]. Chin. J. Org. Chem., 2019, 39(8): 2175-2182.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Scala, A.; Micale, N.; Piperno, A; Rescifina, A.; Schirmeister, T. Kesselring, J.; Grassi, G. RSC Adv. 2016, 6, 30628.
(b) Mishra, A.; Ma, C.-Q.; Bäuerle, P. Chem. Rev. 2009, 109, 1141.
(c) Rasmussen, S. C.; Evenson, S. J.; McCausland, C. B. Chem. Commun. 2015, 51, 4528.
(d) Gopalsamy, A.; Aplasca, A.; Ciszewski, G.; Park, K.; Ellingboe, J. W.; Orlowski, M.; Feld, B. Med. Chem. Lett. 2006, 16, 457.
[2] (a) Wright, J. B.; Johnson, H. G. J. Med. Chem. 1973, 16, 861.
(b) Gabbutt, C. D.; Heoworth, J. D.; Heron, B. M.; Thomas, J. L. Chem. Commun. 1999, 541.
[3] (a) Wang, Z.-G.; Yang, M.-F.; Yang, Y.-D. Org. Lett. 2018, 20, 3001.
(b) Tan, G.-Y.; You, Q.-L.; Lan, J.-B, You, J.-S. Angew. Chem., Int. Ed. 2018, 57, 6309.
(c) Qin, X.-R.; Li, X.-Y.; Huang, Q, Liu, H.; Wu, D.; Guo, Q.; Lan, J.-B.; Wang, R.-L.; You, J.-S. Angew. Chem. Int. Ed. 2015, 54, 7167.
[4] Pradhan, T. K.; De, A. Tetrahedron Lett. 2005, 46, 1493.
[5] (a) Caruana, L.; Forch, M.; Bernardi, L. Synlett. 2017, 28, 1530.
(b) Evans, C. S.; Davis, L. O. Molecules 2018, 23, 33.
(c) Chauhan, P.; Mahajan, S.; Enders, D. Acc. Chem. Res. 2017, 50, 2809.
(d) Volla, C. M.; Atodiresei, L.; Rueping, M. Chem. Rev. 2014, 114, 2390.
(e) Zheng, J.; He, M.; Xie, B.-H.; Yang, L.; Hu, Z.; Zhou, H.-B.; Dong, C. Org. Biomol. Chem. 2018, 16, 472.
[6] Ma, S.; Yu, A.; Zhang, L.; Meng, X. J. Org. Chem. 2018, 83, 5410.
[7] Ma, S.; Yu, A.; Meng, X. Org. Biomol. Chem. 2018, 16, 2885.
[8] (a) Jia, J.; Yu, A.; Ma, S.; Zhang, Y.; Li, K.; Meng, X. Org. Lett. 2017, 19, 6084.
(b) Zhang, Y.; Yu, A.; Jia, J.; Ma, S.; Li, K.; Wei, Y.; Meng, X. Chem. Commun. 2017, 53, 10672.
(c) Ding W.; Zhang, Y.; Yu, A.; Zhang, L.; Meng, X. J. Org. Chem. 2018, 83, 13821.
[9] Allenoate as one carbon synthon:(a) Meng, X.; Huang, Y.; Chen, R. Org. Lett. 2009, 11, 137.
(b) Xu, S.; Zhou, L.; Ma, R.; Song, H.; He, Z. Org. Lett. 2010, 12, 544.
[10] Selected examples of allenoate as two carbon synthon:(a) Gu, Y.; Li, F.; Hu, P.; Liao, D.; Tong, X. Org. Lett. 2015, 17, 1106.
(b) Yang, L.-J.; Li, S.; Wang, S.; Nie, J.; Ma, J.-A. J. Org. Chem. 2014, 79, 3547.
(c) Pei, C.-K.; Jiang, Y.; Wei, Y.; Shi, M. Angew. Chem., Int. Ed. 2012, 51, 11328.
(d) Liu, Y.; Du, Y.; Yu, A.; Qin, D.; Meng, X. Tetrahedron 2015, 71, 7706.
[11] Selected reviews for allenoates:(a) Li, Y.; Chen, X.; Chen, X.; Shen, X. Molecules 2018, 23, 3022.
(b) Chuang, S.-C.; Nallapati, B. S. Asian J. Org. Chem. 2018, 7, 1743.
(c) Wang, Q.-N.; Liu, Z. Q.; Lou, J, Yu, Z. Org. Lett. 2018, 20, 6007.
(d) Yu, Z.-Y.; Jin, Z.-C.; Duan, M, Bai, R.; Lu, Y.; Lan, Y. J. Org. Chem. 2018, 83, 9729.
(e) Vaishanv, N. K.; Gupta, A. K.; Kant, R.; Mohanan, K. J. Org. Chem. 2018, 83, 8759.
[12] Selected examples of allenoate as four carbon synthon:(a) Zhu, X.-F.; Lan, J.; Kwon, O. J. Am. Chem. Soc. 2003, 125, 4716.
(b) Villa, R. A.; Xu, Q.; Kwon, O. Org. Lett. 2012, 14, 4634.
(c) Wang, T.; Ye, S. Org. Lett. 2010, 12, 4168.
(d) Yuan, C.; Zhou, L.; Xia, M.; Sun, Z.; Wang, D.; Guo, H. Org. Lett. 2016, 18, 5644.
[13] CCDC-1913056(3a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam. ac.uk/data_request/cif.

[1]	Shuo Li, Mingliang Wang, Laiyun Zhou, Lanzhi Wang. Magnetic Nano-Supported p-Toluenesulfonic Acid Catalyzed Synthesis of Fused Polycyclic 1,5-Benzoxazepines via Domino Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3977-3988.
[2]	Kai Yang, Meijuan Liu, Yu'na Zhang, Jiaqi Zhan, Luxuan Deng, Xuejie Zheng, Yongjun Zhou, Zhaoyang Wang. Progress in the Synthesis of Benzoheterocycles from 2-Halobenzamides [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2175-2187.
[3]	Futao Peng, Liliang Huang, Junhai Huang, Huangdi Feng. Double aza-Morita-Baylis-Hillman Domino Reaction to Access Amino Derived 1,6-Dienes [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2001-2007.
[4]	Fengcheng Jia, Na Luo, Cheng Xu, Anxin Wu. Recent Advances in the Synthesis of Benzoheterocyclic Compounds Involving Isatins [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1527-1542.
[5]	Xueying Wang, Yee Lin Phang, Changwu Zheng, Hongxi Xu. Studies toward the Total Synthesis of Xanthochymol [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4421-4427.
[6]	Wang Xiang, Chen Ping, Zhi Sanjun, Hu Huayou, Kan Yuhe, Zhang Zaichao. N-Chloro-succinimide-Promoted Efficient Synthesis of Naphthofuran-4,9-dione Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2526-2530.
[7]	Zhao Yu, Wang Weiwei, Liu Xinlei, Geng Rui, Wang Ming'an. Catalyst-Free Domino Reaction of Ethyl 4-Hydroxyalkyl-2-ynoate with N-Heteroarylmethyl-N-2,2-difluoroethan-1-amine [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 694-703.
[8]	Sun Jing, Cao Jun, Han Ying, Yan Chao-Guo. Progress in Multicomponent Reactions Involving 1,3-Indanedione [J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4122-4146.
[9]	Ma Rong, Song Gege, Xi Qiuzhen, Yang Liu, Li Er-Qing, Duan Zheng. Phosphine-Catalyzed[3+2] Annulations with γ-Methyl Allenoates [J]. Chin. J. Org. Chem., 2019, 39(8): 2196-2202.
[10]	Liang Tingting, Jiang Lan, Gan Miaomiao, Su Xin, Li Zhengning. Domino Reactions Initialized by Copper-Catalyzed Hydrocupration of C-C Unsaturated Bonds [J]. Chin. J. Org. Chem., 2017, 37(12): 3096-3111.
[11]	Rao Yin, Liu Meilin, Yin Guodong. Domino Synthesis of Novel Chromene-Indanedione Derivatives [J]. Chin. J. Org. Chem., 2015, 35(3): 719-723.
[12]	Yan Nan, Xiong Yunkui, Xia Jianhui, Rui Peixin, Lei Zhiwei, Liao Weilin, Xiong Bin. Green Synthesis of Novel Spirooxindole Derivatives in Deep Eutectic Solvent [J]. Chin. J. Org. Chem., 2015, 35(2): 384-389.
[13]	Zhu Hui, Ye Changqing, Chen Zhiyuan. Recent Advances in the Norbornene Mediated Palladium-Catalyzed Domino-Type Catellani Reaction [J]. Chin. J. Org. Chem., 2015, 35(11): 2291-2300.
[14]	Feng Yadong, Zhang Hong, Cheng Guolin, Cui Xiuling. Synthesis of Indole Derivatives via Domino Reactions [J]. Chin. J. Org. Chem., 2014, 34(8): 1499-1508.
[15]	Han Ying, Sun Jing, Sun Yan, Gao Hong, Yan Chaoguo. Development of Domino Reactions with β-Enamino Esters as Key Intermediates [J]. Chin. J. Org. Chem., 2012, 32(9): 1577-1586.

1,4-二氮杂二环[2.2.2]辛烷(DABCO)催化联烯的[4+2]串联反应:合成苯并噻吩并吡喃衍生物

1,4-Diazabicyclo[2.2.2]octane (DABCO)-Catalyzed [4+2] Domino Reaction of Allenoates: Synthesis of Benzo[4,5]thieno-[3,2-b]pyran Derivatives

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments