Efficient Synthesis of Spirocyclic Nucleosides via Michael Addition-Initiated Intermolecular Cyclopropanation Reaction

doi:10.6023/cjoc201904074

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3237-3243.DOI: 10.6023/cjoc201904074 Previous Articles Next Articles

通过Michael加成引发分子间的环丙烷化反应高效合成螺环嘧啶核苷

郝二军^a, 张庆^a, 张齐英^a*(), 渠桂荣^a, 杨西宁^b, 郭海明^a*()

^a河南师范大学化学化工学院精细化学品绿色制造河南省协同创新中心河南省有机功能分子与药物创新重点实验室河南新乡 453007
^b 新乡拓新药业股份有限公司河南新乡 453000

收稿日期:2019-04-30 发布日期:2019-06-24
通讯作者: 张齐英,郭海明 E-mail:zhangqiying@htu.edu.cn;ghm@htu.edu.cn
基金资助:
国家自然科学基金(21602045);国家自然科学基金(U1604283);河南省博士后科学基金(2015071);高等学校学科创新引智计划(111计划);高等学校学科创新引智计划(D17007)

Efficient Synthesis of Spirocyclic Nucleosides via Michael Addition-Initiated Intermolecular Cyclopropanation Reaction

Hao Erjun^a, Zhang Qing^a, Zhang Qiying^a*(), Qu Guirong^a, Yang Xining^b, Guo Haiming^a*()

^aHenan Key Laboratory of Organic Functional Molecules and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
^b Xinxiang Tuoxin Pharmaceutical Co., Ltd., Xinxiang, Henan 453000

Received:2019-04-30 Published:2019-06-24
Contact: Zhang Qiying,Guo Haiming E-mail:zhangqiying@htu.edu.cn;ghm@htu.edu.cn
Supported by:
the National Natural Science Foundation of China(21602045);the National Natural Science Foundation of China(U1604283);the Henan Postdoctoral Science Foundation Funded Project(2015071);Overseas Expertise Introduction Project for Discipline Innovation(111计划);Overseas Expertise Introduction Project for Discipline Innovation(D17007)

1. .pdf(3096KB)

Abstract

Cite this article

Hao Erjun, Zhang Qing, Zhang Qiying, Qu Guirong, Yang Xining, Guo Haiming. Efficient Synthesis of Spirocyclic Nucleosides via Michael Addition-Initiated Intermolecular Cyclopropanation Reaction[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3237-3243.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 5

References 10

[1]	(a) Paquette, L. A.; Owen, D. R.; Bibart, R. T.; Seekamp, C. K. Org. Lett. 2001, 3, 4043.
	(b) Paquette, L. A.; Bibart, R. T.; Seekamp, C. K.; Kahane, A. L. Org. Lett. 2001, 3, 4039.
	(c) Tang, Y. B.; Li, Z. R. Chin. J. Biochem. Pharm. 2004, 25, 44 (in Chinese).
	(汤雁波, 李卓荣, 中国生化药物杂志, 2004, 25, 44.)
	(d) Rungta, P.; Mangla, P.; Maikhuri, V. K.; Singh, S. K.; Prasad. A. K. ChemistrySelect 2017, 2, 7808.
[2]	(a) Prota, A.; Vogt, J.; Pilger, B.; Perozzo, R.; Wurth, C.; Marquez, V. E.; Russ, P.; Schulz, G. E.; Folkers, G.; Scapozza, L. Biochemistry 2000, 39, 9597. doi: 10.1021/bi000668q
	(b) Jacobson, K. A.; Ji, X.; Li, A.; Melman, N.; Siddiqui, M. A.; Shin, K. J.; Marquez, V. E.; Ravi, R. G. J. Med. Chem. 2000, 43, 2196. doi: 10.1021/bi000668q
	(c) Nandanan, E.; Jang, S.-Y.; Moro, S.; Kim, H. O.; Siddiqui, M. A.; Russ, P.; Marquez, V. E.; Busson, R.; Herdewijn, P.; Harden, T. K.; Boyer, J. L.; Jacobson, K. A. J. Med. Chem. 2000, 43, 829. doi: 10.1021/bi000668q
[3]	(a) Lemaire, S.; Diène, C.; Gavryushin, A.; Jourdin, X. M. D.; Paolini, L.; Jusseau, X.; Knochel, P.; Farina, V. J. Org. Chem. 2019, 84, 4910. doi: 10.1021/acs.joc.8b02784
	(b) Kumar, R.; Kumar, M.; Singh, A.; Singh, N.; Maity, J.; Prasad, A. K. Carbohydr. Res. 2017, 445, 88. doi: 10.1021/acs.joc.8b02784
	(c) Cobb, A. J. A.; Del'Isola, A.; Abdulsattar, B. O.; McLachlan, M. M. W.; Neuman, B. W.; Müller, C.; Shankland, K.; Al-Mulla, H. M. N.; Binks, A. W. D.; Elvidgeb, W. New J. Chem. 2018, 42, 18363. doi: 10.1021/acs.joc.8b02784
	(d) Lebreton, J.; Escudier, J.-M.; Arzel, L.; Len, C. Chem. Rev. 2010, 110, 3371. doi: 10.1021/acs.joc.8b02784
[4]	Li H.; Yoo J. C.; Hong J. H. Bull. Korean Chem. Soc. 2011, 32 1146. doi: 10.5012/bkcs.2011.32.4.1146
[5]	Zeng D.; Zhang R.; Nie Q.; Cao L.; Shang L.; Yin Z. ACS Med. Chem. Lett. 2016, 7 1197. doi: 10.1021/acsmedchemlett.6b00270
[6]	Jonckers T. H. M.; Lin T.; Buyck C.; Lachau-Durand S.; Vandyck K.; Hoof S. V.; Vandekerckhove L. A. M.; Hu L.; Berke J. M.; Vijgen L.; Dillen L. L. A.; Cummings M. D.; de Kock H.; Nilsson M.; Sund C.; Rydegård C.; Samuelsson B.; RosenquistÅ.; Fanning G.; Emelen K. V.; Simmen K.; Raboisson P. J. Med. Chem. 2010, 53 8150. doi: 10.1021/jm101050a
[7]	de Castro S.; Lozano A.; Jimeno M.-L.; Pérez-Pérez M.-J.; San-Félix A.; Camarasa M.-J.; Velázquez S. J. Org. Chem. 2006, 71 1407. doi: 10.1021/jo0520588
[8]	Paquette L. A.; Seekamp C. K.; Kahane A. L. J. Org. Chem. 2003, 68 8614. doi: 10.1021/jo0301954
[9]	(a) Dang, S.; Sun, J.; Xu, X.; Wang, P.; Wu, J. Chem. Res. Chin. Univ. 2008, 24, 473.
	(b) Wu, W. M.S. Thesis, Jilin University, Changchun, 2014 (in Chinese).
	(吴为, 硕士论文, 吉林大学, 长春, 2014.)
[10]	Selected examples: (a) Xie, M.-S.; Zhou, P.; Niu, H.-Y.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2016, 18, 4344. doi: 10.1021/acs.orglett.6b02104
	(b) Li, J.-P.; Zhao, G.-F.; Wang, H.-X.; Xie, M.-S.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2017, 19, 6494. doi: 10.1021/acs.orglett.6b02104
	(c) Huang, K.-X.; Xie, M.-S.; Zhang, Q.-Y.; Niu, H.-Y.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2018, 20, 5398. doi: 10.1021/acs.orglett.6b02104
	(d) Guo, Z.; Xie, M.; Han, R.; Qu, G.; Guo, H. Chin. J. Org. Chem. 2018, 38, 112 (in Chinese). doi: 10.1021/acs.orglett.6b02104
	(郭真, 谢明胜, 韩瑞杰, 渠桂荣, 郭海明, 有机化学, 2018, 38, 112.) doi: 10.1021/acs.orglett.6b02104
	(e) Zhang, Y.-M.; Zhang, Q.-Y.; Wang, D.-C.; Xie, M.-S.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2019, 21, 2998. doi: 10.1021/acs.orglett.6b02104


Entry	Base	Solvent	Temp.	Yield^c/%
1	Na₂CO₃	CH₃CN	r.t.	Trace
2	Et₃N	CH₃CN	r.t.	Trace
3	DBU	CH₃CN	r.t.	39
4	K₂CO₃	CH₃CN	r.t.	44
5	Cs₂CO₃	CH₃CN	r.t.	56
6	KO^tBu	CH₃CN	r.t.	60
7	KO^tBu	CH₂Cl₂	r.t.	8
8	KO^tBu	MeOH	r.t.	51
9	KO^tBu	THF	r.t.	17
10	KO^tBu	Toluene	r.t.	Trace
11	KO^tBu	Dioxane	r.t.	12
12	KO^tBu	CH₃CN	35	37
13	KO^tBu	CH₃CN	15	62
14	KO^tBu	CH₃CN	0	66
15	KO^tBu	CH₃CN	－10	73
16	KO^tBu	CH₃CN	－20	84
17	KO^tBu	CH₃CN	－30	79
18^d	KO^tBu	CH₃CN	－20	58
19^e	KO^tBu	CH₃CN	－20	84
20^f	KO^tBu	CH₃CN	－20	82
21^g	KO^tBu	CH₃CN	－20	83


Entry	Base	Solvent	Temp.	Yield^c/%
1	Na₂CO₃	CH₃CN	r.t.	Trace
2	Et₃N	CH₃CN	r.t.	Trace
3	DBU	CH₃CN	r.t.	39
4	K₂CO₃	CH₃CN	r.t.	44
5	Cs₂CO₃	CH₃CN	r.t.	56
6	KO^tBu	CH₃CN	r.t.	60
7	KO^tBu	CH₂Cl₂	r.t.	8
8	KO^tBu	MeOH	r.t.	51
9	KO^tBu	THF	r.t.	17
10	KO^tBu	Toluene	r.t.	Trace
11	KO^tBu	Dioxane	r.t.	12
12	KO^tBu	CH₃CN	35	37
13	KO^tBu	CH₃CN	15	62
14	KO^tBu	CH₃CN	0	66
15	KO^tBu	CH₃CN	－10	73
16	KO^tBu	CH₃CN	－20	84
17	KO^tBu	CH₃CN	－30	79
18^d	KO^tBu	CH₃CN	－20	58
19^e	KO^tBu	CH₃CN	－20	84
20^f	KO^tBu	CH₃CN	－20	82
21^g	KO^tBu	CH₃CN	－20	83

通过Michael加成引发分子间的环丙烷化反应高效合成螺环嘧啶核苷

Efficient Synthesis of Spirocyclic Nucleosides via Michael Addition-Initiated Intermolecular Cyclopropanation Reaction

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 5

References 10

Related Articles 0

Recommended Articles

Metrics

Comments