Divergent Synthesis of Ketone-Fused Indoles/Pyrroles via Metal-Guided Friedel-Crafts Cyclization

doi:10.6023/cjoc202105021

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (9): 3521-3531.DOI: 10.6023/cjoc202105021 Previous Articles Next Articles

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金属引导的发散型傅-克环化反应合成羰基稠合的吲哚/吡咯

罗和江^a, 曹同祥^a^,^*(), 祝诗发^a^,^b^,^*()

a 华南理工大学化学与化工学院广东省功能分子工程重点实验室广州 510640
b 中新国际合作研究院广州 510555

收稿日期:2021-05-11 修回日期:2021-06-03 发布日期:2021-06-07
通讯作者: 曹同祥, 祝诗发
基金资助:
中华人民共和国科技部(2016YFA0602900); 国家自然科学基金(21871096); 国家自然科学基金(22071062); 国家自然科学基金(22001077); 广东省科学技术基金(2018B030308007); 广东省科学技术基金(2018A030310359); 广东省科学技术基金(2021A1515012331); 中国博士后科学基金(2018M643062); 中国博士后科学基金(2019T120723)

Divergent Synthesis of Ketone-Fused Indoles/Pyrroles via Metal-Guided Friedel-Crafts Cyclization

Hejiang Luo^a, Tongxiang Cao^a(), Shifa Zhu^a^,^b()

a Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640
b China-Singapore International Joint Research Institute, Guangzhou 510555

Received:2021-05-11 Revised:2021-06-03 Published:2021-06-07
Contact: Tongxiang Cao, Shifa Zhu
Supported by:
Ministry of Science and Technology of the People's Republic of China(2016YFA0602900); National Natural Science Foundation of China(21871096); National Natural Science Foundation of China(22071062); National Natural Science Foundation of China(22001077); Guangdong Provincal Science and Technology Fund(2018B030308007); Guangdong Provincal Science and Technology Fund(2018A030310359); Guangdong Provincal Science and Technology Fund(2021A1515012331); China Postdoctoral Science Foundation(2018M643062); China Postdoctoral Science Foundation(2019T120723)

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Abstract

A metal-guided method for divergent synthesis of ketone-fused indoles/pyrroles from N-(2-alkynylaryl) lactam is described. The reaction is proposed to proceed through a regioswitchable Friedel-Crafts cyclization of acylium. The obvious advantages are wide substrate scopes, high atom economy and step economy, which have a great potential in the synthesis of structure-related bioactive compounds.

Key words: Friedel-Crafts cyclization, ketone-fused indoles/pyrroles, divergent synthesis

Cite this article

Hejiang Luo, Tongxiang Cao, Shifa Zhu. Divergent Synthesis of Ketone-Fused Indoles/Pyrroles via Metal-Guided Friedel-Crafts Cyclization[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3521-3531.

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[1]	(a) Michael, J. P. The Alkaloids: Chemistry and Biology 2001, 55, 91.
	(b) Michael, J. P. The Alkaloids: Chemistry and Biology 2016, 75, 1.
[2]	Estévez, V.; Villacampa, M.; Menéndez, J. C. Chem. Soc. Rev. 2014, 43, 4633. doi: 10.1039/C3CS60015G
[3]	Huckaba, A. J.; Giordano, F.; McNamara, L. E.; Dreux, K. M.; Hammer, N. I.; Tschumper, G. S.; Zakeeruddin, S. M.; Grätzel, M.; Nazeeruddin, M. K.; Delcamp, J. H. Adv. Energy Mater. 2015, 5, 1401629. doi: 10.1002/aenm.201401629
[4]	(a) Lee, C.; Sohn, J. H.; Jang, J.-H.; Ahn, J. S.; Oh, H.; Baltrusaitis, J.; Hwang, I. H.; Gloer, J. B. J. Antibiot. 2015, 68, 715. doi: 10.1038/ja.2015.56 pmid: 16525547
	(b) van Wijngaarden, I.; Hamminga, D.; van Hes, R.; Standaar, P. J.; Tipker, J.; Tulp, M. T. M.; Mol, F.; Olivier, B.; de Jonge, A. J. Med. Chem. 1993, 36, 3693. pmid: 16525547
	(c) Dinsmore, A.; Mandy, K.; Michael, J. P. Org. Biomol. Chem. 2006, 4, 1032. pmid: 16525547
	(d) Sun, L.-R.; Li, X.; Wang, S.-X. J. Asian Nat. Prod. Res. 2005, 7, 127. doi: 10.1080/10286020310001625157 pmid: 16525547
[5]	(a) Johnson, T. O.; Ermolieff, J.; Jirousek, M. R. Nat. Rev. Drug Discov. 2002, 1, 696. doi: 10.1038/nrd895 pmid: 19410499
	(b) Vintonyak, V. V.; Antonchick, A. P.; Rauh, D.; Waldmann, H. Curr. Opin. Chem. Biol. 2009, 13, 272. doi: 10.1016/j.cbpa.2009.03.021 pmid: 19410499
[6]	(a) Peat, A. J.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 1028. doi: 10.1021/ja953080t pmid: 22260312
	(b) Liras, S.; Lynch, C. L.; Fryer, A. M.; Vu, B. T.; Martin, S. F. J. Am. Chem. Soc. 2001, 123, 5918. pmid: 22260312
	(c) Kato, K.; Ono, M.; Akita, H. Tetrahedron 2001, 57, 10055. doi: 10.1016/S0040-4020(01)01068-7 pmid: 22260312
	(d) Yadav, A. K.; Peruncheralathan, S.; Ila, H.; Junjappa, H. J. Org. Chem. 2007, 72, 1388. pmid: 22260312
	(e) Takaya, J.; Udagawa, S.; Kusama, H.; Iwasawa, N. Angew. Chem., Int. Ed. 2008, 47, 4906. pmid: 22260312
	(f) Stoffman, E. J. L.; Clive, D. L. J. Tetrahedron 2010, 66, 4452. doi: 10.1016/j.tet.2010.04.081 pmid: 22260312
	(g) Allan, K. M.; Kobayashi, K.; Rawal, V. H. J. Am. Chem. Soc. 2012, 134, 1392. doi: 10.1021/ja210793x pmid: 22260312
	(h) Quasdorf, K. W.; Huters, A. D.; Lodewyk, M. W.; Tantillo, D. J.; Garg, N. K. J. Am. Chem. Soc. 2012, 134, 1396. doi: 10.1021/ja210837b pmid: 22260312
	(i) Umezaki, S.; Yokoshima, S.; Fukuyama, T. Org. Lett. 2013, 15, 4230. doi: 10.1021/ol4019562 pmid: 22260312
	(j) Xu, X.-B.; Liu, J.; Zhang, J.-J.; Wang, Y.-W.; Peng, Y. Org. Lett. 2013, 15, 550. doi: 10.1021/ol303366u pmid: 22260312
	(k) Layek, M.; Reddy M, A.; Dhanunjaya Rao, A. V.; Alvala, M.; Arunasree, M. K.; Islam, A.; Mukkanti, K.; Iqbal, J.; Pal, M. Org. Biomol. Chem. 2011, 9, 1004. doi: 10.1039/C0OB00771D pmid: 22260312
	(l) Ni, Q.; Zhang, H.; Grossmann, A.; Loh, C. C. J.; Merkens, C.; Enders, D. Angew. Chem., Int. Ed. 2013, 52, 13562. doi: 10.1002/anie.201305957 pmid: 22260312
	(m) Park, J.; Kim, D.-H.; Das, T.; Cho, C.-G. Org. Lett. 2016, 18, 5098. pmid: 22260312
	(n) Li, W.; Dong, Z.; Zhang, Y.; Zeng, Z.; Usman, M.; Liu, W.-B. J. Org. Chem. 2019, 84, 7995. doi: 10.1021/acs.joc.9b00866 pmid: 22260312
	(o) Dong, Z.; Zhang, X.-W.; Li, W.; Li, Z.-M.; Wang, W.-Y.; Zhang, Y.; Liu, W.; Liu, W.-B. Org. Lett. 2019, 21, 1082. doi: 10.1021/acs.orglett.8b04128 pmid: 22260312
	(p) Yang, X.; Luo, G.; Zhou, L.; Liu, B.; Zhang, X.; Gao, H.; Jin, Z.; Chi, Y. R. ACS Catal. 2019, 9, 10971. doi: 10.1021/acscatal.9b03163 pmid: 22260312
	(q) Harada, S.; Yanagawa, M.; Nemoto, T. ACS Catal. 2020, 10, 11971. doi: 10.1021/acscatal.0c03940 pmid: 22260312
	(r) Occhiato, E. G.; Prandi, C.; Ferrali, A.; Guarna, A. J. Org. Chem. 2005, 70, 4542. pmid: 22260312
	(s) Schwier, T.; Sromek, A. W.; Yap, D. M. L.; Chernyak, D.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 9868. pmid: 22260312
	(t) Lu, S.-C.; Wang, W.-X.; Gao, P.-L.; Zhang, W.; Tu, Z.-F. Org. Biomol. Chem. 2012, 10, 232. doi: 10.1039/C1OB05954H pmid: 22260312
	(u) Jiang, B.; Li, Y.; Tu, M.-S.; Wang, S.-L.; Tu, S.-J.; Li, G. J. Org. Chem. 2012, 77, 7497. doi: 10.1021/jo301323r pmid: 22260312
	(v) Jiang, B.; Li, Q.-Y.; Zhang, H.; Tu, S.-J.; Pindi, S.; Li, G. Org. Lett. 2012, 14, 700. doi: 10.1021/ol203166c pmid: 22260312
	(w) Alford, J. S.; Spangler, J. E.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 11712. doi: 10.1021/ja405043g pmid: 22260312
	(x) Zheng, Z.; Tu, H.; Zhang, L. Chem. Eur. J. 2014, 20, 2445. doi: 10.1002/chem.v20.9 pmid: 22260312
	(y) Chen, J.; Chang, D.; Xiao, F.; Deng, G.-J. J. Org. Chem. 2019, 84, 568. doi: 10.1021/acs.joc.8b02410 pmid: 22260312
	(z) Li, W.; Usman, M.; Wu, L.-Y.; Liu, W.-B. J. Org. Chem. 2019, 84, 15754. doi: 10.1021/acs.joc.9b02672 pmid: 22260312
	(aa) Sun, K.; Lei, J.; Liu, Y.; Liu, B.; Chen, N. Adv. Synth. Catal. 2020, 362, 3709. doi: 10.1002/adsc.v362.18 pmid: 22260312
	(ab) Xu, X.; Chen, J.; Ke, J.; Zhang, K.; Wu, P.; Wang, S. Chin. J. Org. Chem. 2021, 41, 206. (in Chinese). doi: 10.6023/cjoc202005018 pmid: 22260312
	( 徐学涛, 陈洁, 柯俊杰, 张焜, 吴盼盼, 王少华, 有机化学, 2021, 41, 206.) pmid: 22260312
	(ac) Du, Y.; Xiao, Y.; Tian, F.; Han, L.; Gu, Y.; Zhu, N. Chin. J. Org. Chem. 2021, 41, 521. (in Chinese). doi: 10.6023/cjoc202007014 pmid: 22260312
	( 杜玉英, 肖业元, 田福利, 韩利民, 顾彦龙, 竺宁, 有机化学, 2021, 41, 521.) pmid: 22260312
	(ad) Zhou, B.; Liang, R.; Cao, Z.; Zhou, P.; Jia, Y. Acta Chim. Sinica 2021, 79, 176. (in Chinese). doi: 10.6023/A20110520 pmid: 22260312
	( 周波, 梁仁校, 曹中艳, 周平海, 贾义霞, 化学学报, 2021, 79, 176.) pmid: 22260312
	(ae) Liu, Y.-H.; Song, H.; Zhang, C.; Liu, Y.-J.; Shi, B.-F. Chin. J. Chem. 2020, 38, 1545. doi: 10.1002/cjoc.v38.12 pmid: 22260312
[7]	(a) Li, G.; Huang, X.; Zhang, L. Angew. Chem., Int. Ed. 2008, 47, 346. doi: 10.1002/(ISSN)1521-3773 pmid: 18954058
	(b) Peng, Y.; Yu, M.; Zhang, L. Org. Lett. 2008, 10, 5187. doi: 10.1021/ol802159v pmid: 18954058
[8]	(a) Liu, L.; Wang, Y.; Zhang, L. Org. Lett. 2012, 14, 3736. doi: 10.1021/ol301593w
	(b) Zheng, Z.; Touve, M.; Barnes, J.; Reich, N.; Zhang, L. Angew. Chem., Int. Ed. 2014, 53, 9302. doi: 10.1002/anie.201402268
[9]	(a) Zhang, C.; Jiang, H.; Zhu, S. Chem. Commun. 2017, 53, 2677. doi: 10.1039/C7CC00218A
	(b) Zhu, S.; Zhang, Z.; Huang, X.; Jiang, H.; Guo, Z. Chem.-Eur. J. 2013, 19, 4695. doi: 10.1002/chem.201300232
	(c) Luo, K.; Cao, T.; Jiang, H.; Chen, L.; Zhu, S. Org. Lett. 2017, 19, 5856. doi: 10.1021/acs.orglett.7b02834
	(d) Luo, H.; Liang, R.; Chen, L.; Jiang, H.; Zhu, S. Org. Chem. Front. 2018, 5, 1160. doi: 10.1039/C7QO01122A
	(e) Cao, T.; Chen, L.; Zhu, S. Org. Lett. 2019, 21, 90. doi: 10.1021/acs.orglett.8b03519
	(f) Luo, H.; He, C.; Jiang, H.; Jiang, Zhu, S. Chin. J. Chem. 2020, 38, 1052. doi: 10.1002/cjoc.v38.10
	(g) Zhang, L.; Shi, Q.; Cao, T.; Zhu, S. Chem. Commun. 2020, 56, 9533. doi: 10.1039/D0CC04309E
	(h) Guan, Z.; Zhu, H. Chin. J. Org. Chem. 2020, 40, 1398. (in Chinese). doi: 10.6023/cjoc202000024
	( 关正辉, 祝海涛, 有机化学, 2020, 40, 1398.)
	(i) Zhang, Z.; Jiao, N. Chin. J. Org. Chem. 2020, 40, 1790. (in Chinese). doi: 10.6023/cjoc202000031
	( 张梓曜, 焦宁, 有机化学, 2020, 40, 1790.)
	(j) Liu, X.; Xu, X.; Hu, W. Chin. J. Org. Chem. 2020, 40, 4370. (in Chinese). doi: 10.6023/cjoc202000085
	( 刘向荣, 徐新芳, 胡文浩, 有机化学, 2020, 40, 4370.)
[10]	Tikhe, J. G.; Webber, S. E.; Hostomsky, Z.; Maegley, K. A.; Ekkers, A.; Li, J.; Yu, X.-H.; Almassy, R. J.; Kumpf, R. A.; Boritzki, T. J.; Zhang, C.; Calabrese, C. R.; Curtin, N. J.; Kyle, S.; Thomas, H. D.; Wang, L.-Z.; Calvert, A. H.; Golding, B. T.; Griffin, R. J.; Newell, D. R. J. Med. Chem. 2004, 47, 5467. doi: 10.1021/jm030513r

Entry	Cat. (mol%)	Temp./℃	Yield/%
Entry	Cat. (mol%)	Temp./℃	2a	3a
1	AgSbF₆ (5)	80	15	ND
2	IPrAuNTf₂ (5)	80	45	43
3	Hg(OTf)₂ (5)	80	41	ND
4	AgSbF₆ (5)	Reflux	21	ND
5	AgNTf₂ (5)	Reflux	28	ND
6	AgNTf₂ (10)	Reflux	48	ND
7	AgNTf₂ (20)	Reflux	72^b	ND
8	Hg(OTf)₂ (10)	60	61	ND
9	PdCl₂ (10)	Reflux	16	53^b
10	Pd(PhCN)₂Cl₂ (10)	Reflux	11	34
11	Pd(cod)Cl₂ (10)	Reflux	12	43
12	Pd(PPh₃)₄ (10)	Reflux	39	ND
13	—	Reflux	ND	ND

Entry	Cat. (mol%)	Temp./℃	Yield/%
Entry	Cat. (mol%)	Temp./℃	2a	3a
1	AgSbF₆ (5)	80	15	ND
2	IPrAuNTf₂ (5)	80	45	43
3	Hg(OTf)₂ (5)	80	41	ND
4	AgSbF₆ (5)	Reflux	21	ND
5	AgNTf₂ (5)	Reflux	28	ND
6	AgNTf₂ (10)	Reflux	48	ND
7	AgNTf₂ (20)	Reflux	72^b	ND
8	Hg(OTf)₂ (10)	60	61	ND
9	PdCl₂ (10)	Reflux	16	53^b
10	Pd(PhCN)₂Cl₂ (10)	Reflux	11	34
11	Pd(cod)Cl₂ (10)	Reflux	12	43
12	Pd(PPh₃)₄ (10)	Reflux	39	ND
13	—	Reflux	ND	ND

金属引导的发散型傅-克环化反应合成羰基稠合的吲哚/吡咯

Divergent Synthesis of Ketone-Fused Indoles/Pyrroles via Metal-Guided Friedel-Crafts Cyclization

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