Synthesis of Bicyclic ortho-Aminocarbonitrile Derivatives Catalyzed by 1,4-Diazabicyclo[2.2.2]octane

doi:10.6023/cjoc201901023

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (9): 2560-2566.DOI: 10.6023/cjoc201901023 Previous Articles Next Articles

ARTICLE

1,4-二氮杂双环[2.2.2]辛烷催化双环邻-氨基腈衍生物的合成

颜世强^a,b, 董道青^a, 解春文^b, 王文笙^b, 王祖利^a

a 青岛农业大学化学与药学院青岛 266109;
b 山东达因海洋生物制药股份有限公司威海 264300

收稿日期:2019-01-17 修回日期:2019-04-20 发布日期:2019-04-26
通讯作者: 王祖利 E-mail:wangzulichem@163.com
基金资助:
国家自然科学基金（Nos.81573340，21402103，21772107）、山东省自主创新及成果转化专项（No.2015ZDXX0302A02）及青岛农业大学高层次人才基金（No.631303）资助项目.

Synthesis of Bicyclic ortho-Aminocarbonitrile Derivatives Catalyzed by 1,4-Diazabicyclo[2.2.2]octane

Yan Shiqiang^a,b, Dong Daoqing^a, Xie Chunwen^b, Wang Wensheng^b, Wang Zuli^a

a Qingdao Agricultural University, College of Chemistry and Pharmaceutical Sciences, Qingdao, 266109;
b Shandong Dyne Marine Biopharmaceutical Co., Ltd., Weihai, 264300

Received:2019-01-17 Revised:2019-04-20 Published:2019-04-26
Contact: 10.6023/cjoc201901023 E-mail:wangzulichem@163.com
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 81573340, 21402103, 21772107), the Special Projects for Independent Innovation and Achievement Transformation of Shandong Province (No. 2015ZDXX0302A02) and the Research Fund of Qingdao Agricultural University Highlevel Person (No. 631303).

1. Synthesis of Bicyclic ortho-Aminocarbonitrile Derivatives Catalyzed by 1,4-Diazabicyclo[2.2.2]octane.PDF(7017KB)

Abstract

One-pot three-component reactions catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) for the synthesis of bicyclic ortho-aminocarbonitrile derivatives (21 examples, 68%~96%) have been developed. The reactions proceeded smoothly at room temperature and generated the corresponding products in short reaction time with high to excellent yields. Importantly, the desired products could be easily collected through simple filtration and washing with ethanol.

Key words: 1,4-diazabicyclo[2.2.2]octane (DABCO), multicomponent reaction, ortho-aminocarbonitrile derivatives, environmentally benign, ethanol

Cite this article

Yan Shiqiang, Dong Daoqing, Xie Chunwen, Wang Wensheng, Wang Zuli. Synthesis of Bicyclic ortho-Aminocarbonitrile Derivatives Catalyzed by 1,4-Diazabicyclo[2.2.2]octane[J]. Chin. J. Org. Chem., 2019, 39(9): 2560-2566.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Tang, M.; Wu Y.; Liu Y.; Cai M.; Xia F.; Liu S.; Hu W.; Wu, Y. Acta Chim. Sinica 2016, 74, 54(in Chinese). (唐敏, 吴永, 刘源, 蔡茂强, 夏飞, 刘顺英, 胡文浩, 化学学报, 2016, 74, 54.)
(b) Yu, S.; Fu, X.; Liu, G.; Qiu, H.; Hu, W. Acta Chim. Sinica 2018, 76, 895(in Chinese). (余思凡, 傅祥, 刘耿鑫, 邱晃, 胡文浩, 化学学报, 2018, 76, 895.)
(c) Lu, L.-H.; Zhou, S.-J.; Sun, M.; Chen, J.-L.; Xia, W.; Yu, X.; Xu, X.; He, W.-M. ACS Sustainable Chem. Eng. 2019, 7, 1574.
(d) Wu, C.; Xiao, H.-J.; Wang, S.-W.; Tang, M.-S.; Tang, Z.-L.; Xia, W.; Li, W.-F.; Cao, Z.; He, W.-M. ACS Sustainable Chem. Eng. 2019, 7, 2169.
(e) Wu, C.; Hong, L.; Shu, H.; Zhou, Q.-H.; Wang, Y.; Su, N.; Jiang, S.; Cao, Z.; He, W.-M. ACS Sustainable Chem. Eng. 2019, 7, 8798.
(f) Wang, Z.; Yang, L.; Liu, H.-L.; Bao, W.-H.; Tan, Y.-Z.; Wang, M.; Tang, Z.; He, W.-M. Chin. J. Org. Chem. 2018, 38, 2639(in Chinese). (王峥, 杨柳, 刘慧兰, 谭英芝, 包文虎, 汪明, 唐子龙, 何卫民, 有机化学, 2018, 38, 2639.)
(g) Liu, Q.; Wang, L.; Yue, H.; Li, J.-S.; Luo, Z.; Wei, W. Green Chem. 2019, 21, 1609.
(h) Wei, W.; Cui, H.; Yue, H.; Yang, D. Green Chem. 2018, 20, 3197.
(i) Wang, L.; Bao, P.; Liu, W.; Liu, S.; Hu, C.; Yue, H.; Yang, D.; Wei, W. Chin. J. Org. Chem. 2018, 38, 3189(in Chinese). (王雷雷, 鲍鹏丽, 刘维伟, 刘思彤, 胡昌松, 岳会兰, 杨道山, 魏伟, 有机化学, 2018, 38, 3189.)
(j) Yue, H.; Bo, P.; Wang, B. L.; Lv, X.; Yang, D.; Wei, W. Chin. J. Org. Chem. 2019, 39, 463(in Chinese). (岳会兰, 鲍鹏丽, 王雷雷, 吕晓霞, 杨道山, 王桦, 魏伟, 有机化学, 2019, 39, 463.)
(k) Xie, L.-Y.; Peng, S.; Fan, T.-G.; Liu, Y.-F.; Sun, M.; Jiang, L.-L.; Wang, X.-X.; Cao, Z.; He, W.-M. Sci. China Chem. 2019, 62, 460.
(l) Li, G.; Gan, Z.; Kong, K.; Dou, X.; Yang, D. Adv. Synth. Catal. 2019, 361, 1808.
(m) Zong, Y.; Lang, Y.; Yang, M.; Li, X.; Fan, X.; Wu, J. Org. Lett. 2019, 21, 1935.
[2] (a) Tan, J.; Guo, Y.; Zeng, F.; Chen, G.; Xie, L.; He, W. Chin. J. Org. Chem. 2018, 38, 1740(in Chinese). (谭家希, 郭也, 曾飞, 陈观荣, 谢龙勇, 何卫民, 有机化学, 2018, 38, 1740.)
(b) Sha, H.-K.; Liu, F.; Lu, J.; Liu, Z.-Q.; Hao, W.-J.; Tang, J.-L.; Tu, S.-J.; Jiang, B. Green Chem. 2018, 20, 3476.
(c) Fan, W.; Chen, K.-Y.; Chen, Q.-P.; Li, G.; Jiang, B. Org. Biomol. Chem. 2017, 15, 6493.
(d) Xie, L.-Y.; Peng, S.; Tan, J.-X.; Sun, R.-X.; Yu, X.; Dai, N.-N.; Tang, Z.-L.; Xu, X.; He, W.-M. ACS Sustainable Chem. Eng. 2018, 6, 16976.
(e) Xie, L.-Y.; Peng, S.; Liu, F.; Liu, Y.-F.; Sun, M.; Tang, Z.-L.; Jiang, S.; Cao, Z.; He, W.-M. ACS Sustainable Chem. Eng. 2019, 7, 7193.
(g) Liu, K.-J.; Fu, Y.-L.; Xie, L.-Y.; Wu, C.; He, W.-B.; Peng, S.; Wang, Z.; Bao, W.-H.; Cao, Z.; Xu, X.; He, W.-M. ACS Sustainable Chem. Eng. 2018, 6, 4916.
[3] (a) Enders, D.; Huettl, M. R. M.; Grondal, C.; Raabe, G. Nature 2006, 441, 861.
(b) Padwa, A. Chem. Soc. Rev. 2009, 38, 3072.
(c) Takumi, M.; Noriaki, O.; Takatoshi, I.; Toshiyuki, M. Tetrahedron Lett. 2000, 41, 1051.
(d) Takumi, M.; Yoshio, I. Tetrahedron 2002, 58, 3155.
(e) Saddiqa, A.; Bukhari, I. H.; Tahir, M. N.; Ahmad, M.; Shafiq, M.; Arshad, M. N. Asian J. Chem. 2015, 27, 969.
[4] (a) Wan, Y.; Zhang, X.; Zhao, L.; Wang, C.; Chen, L.; Liu, G.; Huang, S.; Yue, S.; Zhang, W.; Wu, H. J. Heterocycl. Chem. 2015, 52, 623.
(b) Lohar, T.; Kumbhar, A.; Barge, M.; Salunkhe, R. J. Mol. Liq. 2016, 224, 1102.
(c) Gaikwad, D. S.; Undale, K. A.; Patil, D. B.; Patravale, A. A.; Kamble, A. A. J. Iran. Chem. Soc. 2018, 15, 1175.
(d) Wang, X. S.; Wu, J. R.; Zhou, J.; Zhang, M. M. J. Heterocycl. Chem. 2011, 48, 1056.
(e) Zhang, M. M.; Wu, J. R.; Zhou, J.; Wang, X. S. Synth. Commun. 2012, 42, 599.
[5] (a) Mojtahedi, M. M.; Pourabdi, L.; Abaee, M. S.; Jami, H.; Dini, M.; Halvagar, M. R. Tetrahedron 2016, 72, 1699.
(b) Elinson, M. N.; Ilovaisky, A. I.; Merkulova, V. M.; Barba, F.; Batanero, B. Tetrahedron 2013, 69, 7125.
(c) Khan, M. N.; Pal, S.; Karamthulla, S.; Choudhury, L. H. RSC Adv. 2014, 4, 3732.
(d) Wang, J.; Li, Q.; Qi, C.; Liu, Y.; Ge, Z.; Li, R. Org. Biomol. Chem. 2010, 8, 4240.
(e) Babu, T. H.; Joseph, A. A.; Muralidharan, D.; Perumal, P. T. Tetrahedron Lett. 2010, 51, 994.
(f) Elinson, M. N.; Vereshchagin, A. N.; Nasybullin, R. F.; Bobrovsky, S. I.; Ilovaisky, A. I.; Merkulova, V. M.; Bushmarinov, I. S.; Egorov, M. P. RSC Adv. 2015, 5, 50421.
[6] Das, P.; Butcher, R. J.; Mukhopadhyay, C. Green Chem. 2012, 14, 1376.
[7] Zhang, L.; Wan, Y.; Zhang, X.; Cui, H.; Zou, H.; Zhou, Q. Wu, H. Tetrahedron Lett. 2015, 56, 4934.
[8] Maleki, B.; Rooky, R.; Rezaei-Seresht, E.; Tayebee R. Org. Prep. Proced. Int. 2017, 49, 557.
[9] (a) Wang, X.; Zhang, M.; Li, Q.; Yao, C.; Tu, S. Tetrahedron 2007, 63, 5265.
(b) Wang, X. S.; Zhou, J.; Yang, K.; Zhang, M. M. Synth. Commun. 2010, 40, 1065.
[10] Molla, A.; Hussain, S. RSC Adv. 2014, 4, 29750.
[11] Azizi, N.; Ahooie, T. S.; Hashemi, M. M.; Azizi, N.; Ahooie, T. S.; Hashemi, M. M. J. Mol. Liq. 2017, 246, 221.
[12] Huang, X. F.; Zhang, Y. F.; Qi, Z. H.; Li, N. K.; Geng, Z. C.; Li, K.; Wang, X. W. Org. Biomol. Chem. 2014, 12, 4372.
[13] For selected reactions catalyzed by DABCO see:(a) Maher, D.; Connon, S. Tetrahedron Lett. 2004, 45, 1301.
(b) Luca, C.; Francesco, D. S.; Fabrizio, M. Eur. J. Org. Chem. 2006, 4852.
(c) Baidya, M.; Kobayashi, S.; Brotzel, F.; Schmidhammer, U.; Riedle, E.; Mayr, H. Angew. Chem., Int. Ed. 2007, 46, 6176.
(d) Chandrasekhar, S.; Narsihmulu, C.; Saritha, B.; Sultana, S. Tetrahedron Lett. 2004, 45, 5865.
(e) Murthy, S. N.; Madhav, B.; Nageswar, Y. V. D. Tetrahedron Lett. 2010, 51, 5252.
(f) Zhang, W.; Xu, H. D.; Xu, H.; Tang, W. P. J. Am. Chem. Soc. 2009, 131, 3832.
(g) Meshram, H.M.; Kumar, G. S.; Ramesh, P.; Reddy, B. C. Tetrahedron Lett. 2010, 51, 2580.
(h) Fan, M.; Li, G.; Liang, Y. Tetrahedron 2006, 62, 6782.
(i) Wu, J.; Sun, X. Y.; Li, Y. Z. Eur. J. Org. Chem. 2005, 4271.
[14] Li, M.; Zhou, Z.; Wen, L.; Qiu, Z. J. Org. Chem. 2011, 76, 3054.
[15] Singh, M. S.; Nandi, G. C.; Samai, S. Green Chem. 2012, 14, 447.
[16] Liu, Y. F.; Du, Y. L.; Yu, A. M.; Mu, H. F.; Meng, X. T. Org. Biomol. Chem. 2016, 14, 1226.
[17] Chinchkar, S. M.; Patil, J. D.; Korade, S. N.; Gokavi, G. S.; Shejawal, R. V.; Pore, D. M. Lett. Org. Chem. 2017, 14, 403.
[18] (a) Dong, D.-Q.; Chen, W.-J.; Chen, D.-M.; Li, L.-X.; Li, G.-H.; Wang, Z.-L.; Deng, Q.; Long, S. Chin. J. Org. Chem. 2019, 39, DOI:10.6023/cjoc201904070(in Chinese). (董道青, 陈文静, 陈德茂, 李丽霞, 李光辉, 王祖利, 邓企, 龙姝, 有机化学, 2019, 39, DOI:10.6023/cjoc201904070.)
(b) Dong, D.-Q.; Li, L.-X.; Li, G.-H.; Deng, Q.; Wang, Z.-L.; Long, S. Chin. J. Catal. 2019, 1494.
(c) Xu, X.-M.; Chen, D.-M.; Wang, Z.-L. Chin. J. Org. Chem. 2019, 39, DOI:10.6023/cjoc201904068(in Chinese). (徐鑫明, 陈德茂, 王祖利, 有机化学, 2019, 39, DOI:10.6023/cjoc201904068.)
(d) Hao, S. H.; Zhang, X. Y.; Dong, D. Q.; Wang, Z. L. Chin. Chem. Lett. 2015, 26, 599.
(e) Zhang, H.; Dong, D.-Q.; Hao, S.-H.; Wang, Z. L. RSC Adv. 2016, 6, 8465.
(f) Yan, S. Q.; Ding, N.; Zhang, W.; Wang, P.; Li, Y. X.; Li, M. Carbohydr. Res. 2012, 354, 6.
(g) Chun, Y. X.; Yan, S. Q.; Li, X. P.; Ding, N.; Zhang, W.; Wang, P.; Li, M.; Li, Y. X. Tetrahedron Lett. 2011, 52, 6196.
(h) Yan, S. Q.; Ding, N.; Zhang, W.; Wang, P.; Li, Y. X.; Li, M. J. Carbohydr. Chem. 2012, 31, 571.
(i) Hao, S.; Li, L.; Dong, D. Q.; Wang, Z. L.; Yu, X. Tetrahedron Lett. 2018, 59, 4073.
(j) Li, G. H.; Dong, D. Q.; Yang, Y.; Yu, X. Y.; Wang, Z. L. Adv. Synth. Catal. 2019, 361, 832.
(k) Li, G.-H.; Dong, D.-Q.; Yu, X.-Y.; Wang, Z.-L. New J. Chem. 2019, 43, 1667.
(l) Dong, D.-Q.; Chen, W.-J.; Yang, Y.; Gao, X.; Wang, Z.-L. ChemistrySelect 2019, 4, 2480.

1,4-二氮杂双环[2.2.2]辛烷催化双环邻-氨基腈衍生物的合成

Synthesis of Bicyclic ortho-Aminocarbonitrile Derivatives Catalyzed by 1,4-Diazabicyclo[2.2.2]octane

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yurong Zhang, Han Wang, Yongjun Mao, Shiliang Shi. Ni-Catalyzed Three-Component Coupling Reaction of Butadiene,Aldimines and Alkenylboronic Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1198-1209.
[2]	Siyu Mu, Hongxia Li, Zhilin Wu, Junmei Peng, Jinyang Chen, Weimin He. Electrocatalytic Three-Component Synthesis of 4-Bromopyrazoles from Acetylacetone, Hydrazine and Diethyl Bromomalonate [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4292-4299.
[3]	Ting Wang, Jingchao Chen, Lun Wang, Zheting Wang, Baomin Fan. Asymmetric Transfer Hydrogenation of α-Aryl Amidates Using Methanol as Hydrogen Source [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3693-3703.
[4]	Honghao Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Using 2-Indolylmethanols as Platform Molecules [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3351-3372.
[5]	Weiqing Ma, Ying Han, Jin Sun, Chaoguo Yan. Three-Component Reaction for Efficient Synthesis of Functionalized Spiro[cyclopentane-1,3'-indolines] [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3180-3191.
[6]	Yu-Qing Li, Shi-Liang Shi. Nickel-Catalyzed Multicomponent Coupling of Butadiene, Aldehydes, Alkynes and Schwartz Reagent to Form 1,4-Dienes [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1939-1948.
[7]	Rong Wang, Lichen Xu, Yi Lu, Bo Jiang, Wenjuan Hao. Sc(OTf)₃-Catalyzed Dearomatization of Indoles for the Synthesis of 3,3'-Bisindoles [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1582-1590.
[8]	Guodong Yin, Yuan Li, Ling Fan. ZrCl4-Catalyzed Synthesis of Pyrimido[4,5-b]quinolin-2,4-(1H,3H)- diones and 11H-Indeno[1,2-b]quinolin-11-ones [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1234-1240.
[9]	Qiang Yan, Rong Fan, Binbin Liu, Shuaisong Su, Bo Wang, Tuanli Yao, Jiajing Tan. Recent Progress in Aryne Participated Dearomatization Reactions [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 455-470.
[10]	Xiao Liwei, Liu Guangxian, Li Zheng, Ren Ping, Ren Lilei, Kong Jie. Synthesis of N-Substituted Decahydroacridine-1,8-diones Promoted by Deep Eutectic Solvents [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2988-2993.
[11]	Zhou Cong, Li Miao, Yu Jintao, Sun Song, Cheng Jiang. Recent Progress in the Carboxylation/Cyclization Reactions Using Carbon Dioxide as the C1 Source [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2221-2231.
[12]	Yan Feng, Cai Shuang, Wen Wu, Wen Wei, Li Bojie, Wang Liansheng, Zhu Lei. Recent Advances and Applications in N-Methylation of Amines and Imines [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1874-1890.
[13]	Yan Lijun, Yan Yuxin, Chen Xuebing, Wang Yongchao. Advances in Multicomponent Asymmetric Cascade Synthesis Involving Hydrogen-Bond-Activated Nitroolefins [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 856-872.
[14]	Yan Lijun, Xu Han, Wang Yan, Dong Jianwei, Wang Yongchao. Advances in Multicomponent Asymmetric Cascade Synthesis Involving Nitroolefin Catalyzed by Diarylprolinol Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 284-299.
[15]	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.