Sc(OTf)3-Catalyzed Reaction of Purines with o-Hydroxybenzyl Alcohols for Construction of Acyclic Nucleosides

doi:10.6023/cjoc202106010

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4391-4399.DOI: 10.6023/cjoc202106010 Previous Articles Next Articles

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三氟甲磺酸钪催化嘌呤与邻羟基苄醇反应构建非环核苷

夏超^a, 王东超^b, 郭海明^a^,^b^,^*()

a 河南师范大学环境学院河南新乡 453007
b 河南师范大学化学化工学院绿色化学介质与反应教育部重点实验室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

收稿日期:2021-06-05 修回日期:2021-07-16 发布日期:2021-08-17
通讯作者: 郭海明
基金资助:
国家自然科学基金(22071046); 中原学者(212101510004); 中央引导地方科技发展专项资金(YDZX20204100001786)

Sc(OTf)₃-Catalyzed Reaction of Purines with o-Hydroxybenzyl Alcohols for Construction of Acyclic Nucleosides

Chao Xia^a, Dongchao Wang^b, Haiming Guo^a^,^b()

a School of Environment, Henan Normal University, Xinxiang, Henan 453007
b Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007

Received:2021-06-05 Revised:2021-07-16 Published:2021-08-17
Contact: Haiming Guo
Supported by:
National Natural Science Foundation of China(22071046); Zhongyuan Scholar(212101510004); National Government Guides Local Special Funds for the Development of Science and Technology(YDZX20204100001786)

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Abstract

Efficient alkylation of purines with ortho-hydroxybenzyl alcohols under mild condition has been achieved by Sc(OTf)₃ catalysis. This C—N bond formation process is proposed to proceed through an ortho-quinone methide intermediate. The reaction allows for efficient synthesis of various acyclic nucleoside analogs, with excellent yields of up to 96%, across a broad range of substrates and the yields were maintained as the reactions were scaled up.

Key words: purine acyclic nucleosides, ortho-quinone methide, scandium catalysis, alkylation reaction

Cite this article

Chao Xia, Dongchao Wang, Haiming Guo. Sc(OTf)₃-Catalyzed Reaction of Purines with o-Hydroxybenzyl Alcohols for Construction of Acyclic Nucleosides[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4391-4399.

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References 13

[1]	(a) Willis, N. J.; Bray, C. D. Chem.-Eur. J. 2012, 18, 9160. doi: 10.1002/chem.201200619 pmid: 27513764
	(b) Bai, W.-J.; David, J. G.; Feng, Z.-G.; Weaver, M. G.; Wu, K.-L.; Pettus, T. R. R. Acc. Chem. Res. 2014, 47, 3655. doi: 10.1021/ar500330x pmid: 27513764
	(c) Jaworski, A. A.; Scheidt, K. A. J. Org. Chem. 2016, 81, 10145. pmid: 27513764
	(d) Yang, B.; Gao, S. Chem. Soc. Rev. 2018, 47, 7926. doi: 10.1039/C8CS00274F pmid: 27513764
[2]	(a) Meisinger, N.; Roiser, L.; Monkowius, U.; Himmelsbach, M.; Robiette, R.; Waser, M. Chem.-Eur. J. 2017, 23, 5137. doi: 10.1002/chem.201700171 pmid: 30407018
	(b) Suneja, A.; Schneider, C. Org. Lett. 2018, 20, 7576. doi: 10.1021/acs.orglett.8b03311 pmid: 30407018
	(c) Pandit, R. P.; Kim, S. T.; Ryu, D. H. Angew. Chem., Int. Ed. 2019, 58, 13427. doi: 10.1002/anie.v58.38 pmid: 30407018
[3]	(a) Bu, H.-Z.; Li, H.-H.; Luo, W.-F.; Luo, C.; Qian, P.-C.; Ye, L.-W. Org. Lett. 2020, 22, 648. doi: 10.1021/acs.orglett.9b04421
	(b) Feng, S.; Yang, B.; Chen, T.; Wang, R.; Deng, Y.-H.; Shao, Z. J. Org. Chem. 2020, 85, 5231. doi: 10.1021/acs.joc.9b03302
	(c) Huang, H.-M.; Wu, X.-Y.; Leng, B.-R.; Zhu, Y.-L.; Meng, X.-C.; Hong, Y.; Jiang, B.; Wang, D.-C. Org. Chem. Front. 2020, 7, 414. doi: 10.1039/C9QO01343A
	(d) Shi, H.; Wang, L.; Li, S.-S.; Liu, Y.; Xu, L. Org. Chem. Front. 2020, 7, 747. doi: 10.1039/D0QO00038H
	(e) Tanaka, K.; Asada, Y.; Hoshino, Y.; Honda, K. Org. Biomol. Chem. 2020, 18, 8074. doi: 10.1039/D0OB01151G
	(f) Tu, M.-S.; Liu, S.-J.; Zhong, C.; Zhang, S.; Zhang, H.; Zheng, Y.-L.; Shi, F. J. Org. Chem. 2020, 85, 5403. doi: 10.1021/acs.joc.0c00119
	(g) You, Y.; Li, T.-T.; Yuan, S.-P.; Xie, K.-X.; Wang, Z.-H.; Zhao, J.-Q.; Zhou, M.-Q.; Yuan, W.-C. Chem. Commun. 2020, 56, 439. doi: 10.1039/C9CC08316B
[4]	(a) Mei, G.-J.; Zhu, Z.-Q.; Zhao, J.-J.; Bian, C.-Y.; Chen, J.; Chen, R.-W.; Shi, F. Chem. Commun. 2017, 53, 2768. doi: 10.1039/C6CC09775H
	(b) Lam, H.; Qureshi, Z.; Wegmann, M.; Lautens, M. Angew. Chem., Int. Ed. 2018, 57, 16185. doi: 10.1002/anie.v57.49
	(c) Sun, M.; Ma, C.; Zhou, S.-J.; Lou, S.-F.; Xiao, J.; Jiao, Y.; Shi, F. Angew. Chem., Int. Ed. 2019, 58, 8703. doi: 10.1002/anie.v58.26
	(d) Suneja, A.; Loui, H. J.; Schneider, C. Angew. Chem., Int. Ed. 2020, 59, 5536. doi: 10.1002/anie.v59.14
	(e) Yan, R.-J.; Liu, B.-X.; Xiao, B.-X.; Du, W.; Chen, Y.-C. Org. Lett. 2020, 22, 4240. doi: 10.1021/acs.orglett.0c01283
	(f) Zhou, S.-J.; Sun, M.; Wang, J.-Y.; Yu, X.-Y.; Lu, H.; Zhang, Y.-C.; Shi, F. Eur. J. Org. Chem. 2020, 4301.
[5]	Xia, C.; Wang, D.-C.; Qu, G.-R.; Guo, H.-M. Org. Chem. Front. 2020, 7, 1474. doi: 10.1039/D0QO00128G
[6]	(a) Wang, Y.; Zhang, C.; Wang, H.; Jiang, Y.; Du, X.; Xu, D. Adv. Synth. Catal. 2017, 359, 791. doi: 10.1002/adsc.v359.5 pmid: 29420039
	(b) Wu, J.-L.; Wang, J.-Y.; Wu, P.; Mei, G.-J.; Shi, F. Org. Chem. Front. 2017, 4, 2465. doi: 10.1039/C7QO00649G pmid: 29420039
	(c) Zhou, J.; Huang, W.-J.; Jiang, G.-F. Org. Lett. 2018, 20, 1158. doi: 10.1021/acs.orglett.8b00025 pmid: 29420039
	(d) Wu, Q.; Li, G.-L.; Yang, S.; Shi, X.-Q.; Huang, T.-Z.; Du, X.-H.; Chen, Y. Org. Biomol. Chem. 2019, 17, 3462. doi: 10.1039/C9OB00283A pmid: 29420039
	(e) Chu, M.-M.; Chen, X.-Y.; Wang, Y.-F.; Qi, S.-S.; Jiang, Z.-H.; Xu, D.-Q.; Xu, Z.-Y. J. Org. Chem. 2020, 85, 9491. doi: 10.1021/acs.joc.9b03479 pmid: 29420039
	(f) Zhang, Y.-Z.; Sheng, F.-T.; Zhu, Z.; Li, Z.-M.; Zhang, S.; Tan, W.; Shi, F. Org. Biomol. Chem. 2020, 18, 5688. doi: 10.1039/D0OB01230K pmid: 29420039
[7]	Lai, Z.; Wang, Z.; Sun, J. Org. Lett. 2015, 17, 6058. doi: 10.1021/acs.orglett.5b03072
[8]	(a) Guo, W.; Wu, B.; Zhou, X.; Chen, P.; Wang, X.; Zhou, Y.-G.; Liu, Y.; Li, C. Angew. Chem., Int. Ed. 2015, 54, 4522. doi: 10.1002/anie.201409894
	(b) Lai, Z.; Sun, J. Synlett 2016, 27, 555. doi: 10.1055/s-00000083
	(c) Roy, D.; Panda, G. Tetrahedron 2018, 74, 6270. doi: 10.1016/j.tet.2018.09.009
[9]	(a) Huang, H.; Kang, J. Y. Org. Lett. 2017, 19, 5988. doi: 10.1021/acs.orglett.7b03019 pmid: 29064709
	(b) Gu, X.; Yuan, H.; Jiang, J.; Wu, Y.; Bai, W.-J. Org. Lett. 2018, 20, 7229. doi: 10.1021/acs.orglett.8b03158 pmid: 29064709
[10]	(a) Chen, M.; Han, Y.; Ma, D.; Wang, Y.; Lai, Z.; Sun, J. Chin. J. Chem. 2018, 36, 587. doi: 10.1002/cjoc.v36.7
	(b) Pelayo, S. G.; López, L. A. Eur. J. Org. Chem. 2017, 2017, 6003. doi: 10.1002/ejoc.201701183
	(c) Chen, L.-M.; Zhao, J.; Xia, A.-J.; Guo, X.-Q.; Gan, Y.; Zhou, C.; Yang, Z.-J.; Yang, J.; Kang, T.-R. Org. Biomol. Chem. 2019, 17, 8561. doi: 10.1039/C9OB01780A
	(d) Osyanin, V. A.; Osipov, D. V.; Nakushnov, V. Y.; Zemtsova, M. N.; Klimochkin, Y. N. Chem. Heterocycl. Compd. 2015, 51, 984. doi: 10.1007/s10593-016-1808-8
[11]	(a) Kelley, J. L.; Kelsey, J. E.; Hall, W. R.; Krochmal, M. P.; Schaeffer, H. J. J. Med. Chem. 1981, 24, 753. pmid: 30939009
	(b) Vandenriessche, F.; Snoeck, R.; Janssen, G.; Hoogmartens, J.; Aerschot, A. V.; Clercq, E. D.; Herdewijn, P. J. Med. Chem. 1992, 35, 1458. doi: 10.1021/jm00086a015 pmid: 30939009
	(c) Sekiyama, T.; Hatsuya, S.; Tanaka, Y.; Uchiyama, M.; Ono, N.; Iwayama, S.; Oikawa, M.; Suzuki, K.; Okunishi, M.; Tsuji, T. J. Med. Chem. 1998, 41, 1284. pmid: 30939009
	(d) Hakimelahi, G. H.; Ly, T. W.; Movahedi, A. A. M.; Jain, M. L.; Zakerinia, M.; Davari, H.; Mei, H.-C.; Sambaiah, T.; Moshfegh, A. A.; Hakimelahi, S. J. Med. Chem. 2001, 44, 3710. pmid: 30939009
	(e) Hernández, A.-I.; Balzarini, J.; Karlsson, A.; Camarasa, M.-J.; Pérez, M.-J. J. Med. Chem. 2002, 45, 4254. doi: 10.1021/jm011128+ pmid: 30939009
	(f) Clercq, E. D. J. Med. Chem. 2019, 62, 7322. doi: 10.1021/acs.jmedchem.9b00175 pmid: 30939009
[12]	(a) Palazzolo, M. A.; Nigro, M. J.; Iribarren, A. M.; Lewkowicz, E. S. Eur. J. Org. Chem. 2016, 2016, 921. pmid: 28829913
	(b) Derudas, M.; Vanpouille, C.; Carta, D.; Zicari, S.; Andrei, G.; Snoeck, R.; Brancale, A.; Margolis, L.; Balzarini, J.; McGuigan, C. J. Med. Chem. 2017, 60, 7876. doi: 10.1021/acs.jmedchem.7b01009 pmid: 28829913
	(c) Lee, S.-J.; Ahn, J.-G.; Seo, J.; Ha, H.-J.; Cho, C.-W. Org. Biomol. Chem. 2018, 16, 9477. doi: 10.1039/C8OB02754D pmid: 28829913
	(d) Zhang, H.; Xie, M.; Qu, G.; Chang, J. Org. Lett. 2019, 21, 120. doi: 10.1021/acs.orglett.8b03555 pmid: 28829913
	(e) Baddi, L.; Ouzebla, D.; Mansouri, A.-E.; Smietana, M.; Vasseur, J.-J.; Lazrek, H. B. Nucleosides, Nucleotides Nucleic Acids 2021, 40, 43. doi: 10.1080/15257770.2020.1826516 pmid: 28829913
[13]	(a) Sun, H.-L.; Chen, F.; Xie, M.-S.; Guo, H.-M.; Qu, G.-R.; He, Y.-M.; Fan, Q.-H. Org. Lett. 2016, 18, 2260. doi: 10.1021/acs.orglett.6b00869 pmid: 28901778
	(b) Zhou, P.; Xie, M.-S.; Qu, G.-R.; Li, R.-L.; Guo, H.-M. Asian J. Org. Chem. 2016, 5, 1100. doi: 10.1002/ajoc.201600251 pmid: 28901778
	(c) Liang, L.; Xie, M.-S.; Qin, T.; Zhu, M.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2017, 19, 5212. doi: 10.1021/acs.orglett.7b02482 pmid: 28901778
	(d) Wang, H.-X.; Yu, L.-L.; Xie, M.-S.; Wu, J.; Qu, G-R.; Ding, K.-L.; Guo, H.-M. Chem.-Eur. J. 2018, 24, 1425. doi: 10.1002/chem.v24.6 pmid: 28901778
	(e) Liang, T.; Xie, M.-S.; Qu, G.-R.; Guo, H.-M. Asian J. Org. Chem. 2019, 8, 1405. doi: 10.1002/ajoc.201900227 pmid: 28901778
	(f) Hao, E.-J.; Li, G.-X.; Liang, Y.-R.; Xie, M.-S.; Wang, D.-C.; Jiang, X.-H.; Cheng, J.-Y.; Shi, Z.-X.; Wang, Y.; Guo, H.-M. J. Med. Chem. 2021, 64, 2077. doi: 10.1021/acs.jmedchem.0c01717 pmid: 28901778
	(g) Xia, C.; Wang, D.-C.; Qu, G.-R.; Guo, H.-M. Org. Chem. Front. 2021, 8, 2569. doi: 10.1039/D1QO00272D pmid: 28901778

Entry	LA (x)	Solvent	t/h	Yield^b/%
1	In(OTf)₃ (20)	DCM	12	75
2	Cu(OTf)₂ (20)	DCM	12	68
3	Fe(OTf)₃ (20)	DCM	12	71
4	Sc(OTf)₃ (20)	DCM	12	95
5	Y(OTf)₃ (20)	DCM	12	18
6	Mg(OTf)₂ (20)	DCM	12	10
7	Zn(OTf)₂ (20)	DCM	12	NR
8	TfOH (10)	DCM	12	20
9	Sc(OTf)₃ (10)	DCM	5	94
10	Sc(OTf)₃ (5)	DCM	10	94
11	Sc(OTf)₃ (2.5)	DCM	24	68
12^c	Sc(OTf)₃ (2.5)	DCM	24	58
13^d	Sc(OTf)₃ (2.5)	DCM	24	61
14^e	Sc(OTf)₃ (2.5)	DCM	24	55
15	Sc(OTf)₃ (5)	Toluene	10	74
16	Sc(OTf)₃ (5)	Et₂O	10	NR
17	Sc(OTf)₃ (5)	Acetone	10	81
18	Sc(OTf)₃ (5)	THF	10	NR
19	Sc(OTf)₃ (5)	EA	10	78

Entry	LA (x)	Solvent	t/h	Yield^b/%
1	In(OTf)₃ (20)	DCM	12	75
2	Cu(OTf)₂ (20)	DCM	12	68
3	Fe(OTf)₃ (20)	DCM	12	71
4	Sc(OTf)₃ (20)	DCM	12	95
5	Y(OTf)₃ (20)	DCM	12	18
6	Mg(OTf)₂ (20)	DCM	12	10
7	Zn(OTf)₂ (20)	DCM	12	NR
8	TfOH (10)	DCM	12	20
9	Sc(OTf)₃ (10)	DCM	5	94
10	Sc(OTf)₃ (5)	DCM	10	94
11	Sc(OTf)₃ (2.5)	DCM	24	68
12^c	Sc(OTf)₃ (2.5)	DCM	24	58
13^d	Sc(OTf)₃ (2.5)	DCM	24	61
14^e	Sc(OTf)₃ (2.5)	DCM	24	55
15	Sc(OTf)₃ (5)	Toluene	10	74
16	Sc(OTf)₃ (5)	Et₂O	10	NR
17	Sc(OTf)₃ (5)	Acetone	10	81
18	Sc(OTf)₃ (5)	THF	10	NR
19	Sc(OTf)₃ (5)	EA	10	78

三氟甲磺酸钪催化嘌呤与邻羟基苄醇反应构建非环核苷

Sc(OTf)₃-Catalyzed Reaction of Purines with o-Hydroxybenzyl Alcohols for Construction of Acyclic Nucleosides

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Entry	Yield^b/%	ee^c/%
1	33	20
2	NR	—
3	41	55

Entry	Yield^b/%	ee^c/%
1	33	20
2	NR	—
3	41	55