Rhodium-Catalyzed Tandem Acylmethylation/Annulation Reactions of 2-Aryl-2H-indazoles with Sulfoxonium Ylides: Easy Access to 6-Arylindazolo[2,3-a]quinolines

doi:10.6023/cjoc202206052

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (3): 1187-1196.DOI: 10.6023/cjoc202206052 Previous Articles Next Articles

Special Issue: 中国女科学家专辑

ARTICLES

铑催化2-芳基-2H-吲唑与硫叶立德的酰甲基化/串联环化反应高效构建6-芳基吲唑并[2,3-a]喹啉类衍生物

汤振, 皮超^*(), 吴养洁, 崔秀灵^*()

郑州大学化学学院绿色催化研究中心河南省高校应用化学重点实验室河南省化学生物学与有机化学重点实验室郑州 450052

收稿日期:2022-06-28 修回日期:2022-08-25 发布日期:2022-09-15
通讯作者: 皮超, 崔秀灵
基金资助:
国家重点研发计划国际合作项目基金(2016YFE0132600); 河南省杰出外籍科学家工作室(GZS2020001); 河南省重点研发与推广专项(212102311068)

Rhodium-Catalyzed Tandem Acylmethylation/Annulation Reactions of 2-Aryl-2H-indazoles with Sulfoxonium Ylides: Easy Access to 6-Arylindazolo[2,3-a]quinolines

Zhen Tang, Chao Pi(), Yangjie Wu, Xiuling Cui()

Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Green Catalysis Center and College of Chemistry, Zhengzhou University, Zhengzhou 450052

Received:2022-06-28 Revised:2022-08-25 Published:2022-09-15
Contact: Chao Pi, Xiuling Cui
Supported by:
National Key R&D Program of China(2016YFE0132600); Henan Center for Outstanding Overseas Scientists(GZS2020001); Technological Project of Henan Province(212102311068)

1. .pdf(11961KB)

Abstract

An efficient synthesis of 6-arylindazolo[2,3-a]quinolines starting from 2-aryl-2H-indazoles with sulfoxonium ylides via rhodium(III)-catalyzed C—H activation and cyclization reaction has been described. This transformation features high efficiency, tolerates various functional groups, avoids external oxidant and produces dimethyl sulfoxide (DMSO) and H₂O as the sole by-products. In addition, the scale-up reaction demonstrated the practicability of this protocol in industry.

Key words: 2-aryl-2H-indazoles, sulfoxonium ylides, rhodium-catalyzed, cyclization

Cite this article

Zhen Tang, Chao Pi, Yangjie Wu, Xiuling Cui. Rhodium-Catalyzed Tandem Acylmethylation/Annulation Reactions of 2-Aryl-2H-indazoles with Sulfoxonium Ylides: Easy Access to 6-Arylindazolo[2,3-a]quinolines[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1187-1196.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

References 14

[1]	(a) Facchetti, A. Chem. Mater. 2011, 23, 733. doi: 10.1021/cm102419z
	(b) Wang, C.; Dong, H.; Hu, W.; Liu, Y.; Zhu, D. Chem. Rev. 2012, 112, 2208. doi: 10.1021/cr100380z
	(c) Gsänger, M.; Bialas, D.; Huang, L.; Stolte, M.; Würthner, F. Adv. Mater. 2016, 28, 3615. doi: 10.1002/adma.v28.19
	(d) Konidena, R. K.; Thomas, K. R. J.; Dubey, D. K.; Sahoo, S.; Jou, J. H. Chem. Commun. 2017, 53, 11802. doi: 10.1039/C7CC07139F
	(e) Ansari, A. J.; Joshi, G.; Sharma, P.; Maurya, A. K.; Metre, R. K.; Agnihotri, V. K.; Chandaluri, C. G.; Kumar, R.; Singh, S.; Sawant, D. M. J. Org. Chem. 2019, 84, 3817. doi: 10.1021/acs.joc.8b02845
[2]	(a) Cheng, Y.; Li, G.; Liu, Y.; Shi, Y.; Gao, G.; Wu, D.; Lan, J.; You, J. J. Am. Chem. Soc. 2016, 138, 4730. doi: 10.1021/jacs.5b09241
	(b) Phillips, S. D.; Castle, R. N. J. Heterocycl. Chem. 1980, 17, 1489. doi: 10.1002/jhet.v17:7
	(c) Sharples, D.; Hajós, G.; Riedl, Z.; Csányi, D.; Molnár, J.; Szabó, D. Arch. Pharm. Pharm. Med. Chem. 2001, 334, 269. doi: 10.1002/1521-4184(200109)334:8/9【-逻辑与-】amp;lt;【-逻辑与-】amp;gt;1.0.CO;2-H
[3]	(a) Allard, S.; Forster, M.; Souharce, B.; Scherf, U. Angew. Chem., Int. Ed. 2008, 47, 4070. doi: 10.1002/(ISSN)1521-3773
	(b) Wong, M. Y.; Zysman-Colman, E. Adv. Mater. 2017, 29, 1605444. doi: 10.1002/adma.v29.22
	(c) Stoessel, P.; Joosten, D.; Gerhard, A.WO 2012007086, 2012.
	(d) Stoessel, P.; Heil, H.; Joosten, D.WO 2010086089, 2010.
[4]	(a) Shindoh, N.; Tokuyama, H.; Takemoto, Y.; Takasu, K. J. Org. Chem. 2008, 73, 7451. doi: 10.1021/jo8009243 pmid: 18759484
	(b) Zhao, J.; Wu, C.; Li, P.; Ai, W.; Chen, H.; Wang, C.; Larock, R. C.; Shi, F. J. Org. Chem. 2001, 76, 6837. doi: 10.1021/jo200863e pmid: 18759484
	(c) Zhao, J.; Li, P.; Wu, C.; Chen, H.; Ai, W., Sun, R.; Ren, H.; Larock, R. C.; Shi, F. Org. Biomol. Chem. 2012, 10, 1922. doi: 10.1039/c2ob06611d pmid: 18759484
	(d) Li, L.; Wang, H.; Yang, X.; Kong, L.; Wang, F.; Li, X. J. Org. Chem. 2016, 81, 12038. doi: 10.1021/acs.joc.6b02356 pmid: 18759484
	(e) Zhu, C.; Feng, C.; Yamane, M. Chem. Commun. 2017, 53, 2606. doi: 10.1039/C7CC00562H pmid: 18759484
	(f) Kumar, S.V.; Ellairaja, S.; Satheesh, S.; Vasantha, V. S.; Punniyamurthy, T. Org. Chem. Front. 2018, 5, 2630. doi: 10.1039/C8QO00557E pmid: 18759484
	(g) Guo, S.; Sun, L.; Li, X.; Zhang, X.; Fan, X. Adv. Synth. Catal. 2020, 362, 913. doi: 10.1002/adsc.v362.4 pmid: 18759484
[5]	(a) Rakshit, S.; Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9585. doi: 10.1021/ja104305s pmid: 20578748
	(b) Ackermann, L. Acc. Chem. Res. 2014, 47, 281. doi: 10.1021/ar3002798 pmid: 20578748
	(c) Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651. doi: 10.1039/c2cs15281a pmid: 20578748
	(d) He, J.; Wasa, M.; Chan, K. S. L.; Shao, Q.; Yu, J. Q. Chem. Rev. 2017, 117, 8754. doi: 10.1021/acs.chemrev.6b00622 pmid: 20578748
	(e) Liu, W. P.; Ackermann, L. ACS Catal. 2016, 6, 3743. doi: 10.1021/acscatal.6b00993 pmid: 20578748
[6]	(a) Sambiagio, C.; Schönbauer, D.; Blieck, R.; Dao-Huy, T.; Potot- schnig, G.; Schaaf, P.; Wiesinger, T.; Zia, M. F.; Wencel-Delord, J.; Besset, T.; Maes, B. U. W.; Schnürch, M. Chem. Soc. Rev. 2018, 47, 6603. doi: 10.1039/c8cs00201k pmid: 30033454
	(b) Wu, Y.; Pi, C.; Wu, Y.; Cui, X. Chem. Soc. Rev. 2021, 50, 3677. doi: 10.1039/D0CS00966K pmid: 30033454
[7]	(a) Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2004, 126, 2706. doi: 10.1021/ja0393170 pmid: 29048909
	(b) Zhang, C.; Rao, Y. Org. Lett. 2015, 17, 4456. doi: 10.1021/acs.orglett.5b02115 pmid: 29048909
	(c) Zhang, B.; Wang, H.W.; Kang, Y. S.; Zhang, P.; Xu, H.J.; Lu, Y.; Sun, W.Y. Org. Lett. 2017, 19, 5940. doi: 10.1021/acs.orglett.7b02931 pmid: 29048909
	(d) Xu, F.; Li, Y. J.; Huang, C.; Xu, H. C. ACS Catal. 2018, 8, 3820. doi: 10.1021/acscatal.8b00373 pmid: 29048909
	(e) Zhu, S.; Shi, K.; Zhu, H.; Jia, Z. K.; Xia, X. F.; Wang, D.; Zou, L. H. Org. Lett. 2020, 22, 1504. doi: 10.1021/acs.orglett.0c00085 pmid: 29048909
[8]	Wu, Y.; Pi, C.; Wu, Y.; Cui, X. Org. Lett. 2020, 22, 361. doi: 10.1021/acs.orglett.9b03768
[9]	Hu, W.; Pi, C.; Wu, Y.; Cui, X. Org. Lett. 2020, 22, 2613.
[10]	(a) Li, A. H.; Dai, L. X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341. doi: 10.1021/cr960411r
	(b) Lu, L. Q.; Li, T. R.; Wang, Q.; Xiao, W. J. Chem. Soc. Rev. 2017, 46, 4135. doi: 10.1039/C6CS00276E
	(c) Kaiser, D.; Klose, I.; Oost, R.; Neuhaus, J.; Maulideet, N. Chem. Rev. 2019, 119, 8701. doi: 10.1021/acs.chemrev.9b00111
	(d) Barday, M.; Janot, C.; Halcovitch, N.R.; Muir, J.; Aïssa, C. Angew. Chem., Int. Ed. 2017, 56, 13117. doi: 10.1002/anie.201706804
[11]	(a) Talero, A. G.; Martins, B. S.; Burtoloso, A. C. B. Org. Lett. 2018, 20, 7206. doi: 10.1021/acs.orglett.8b03126 pmid: 30958678
	(b) Ji, S.; Yan, K.; Li, B.; Wang, B. Org. Lett. 2018, 20, 5981. doi: 10.1021/acs.orglett.8b02796 pmid: 30958678
	(c) You, C.; Pi, C.; Wu, Y.; Cui, X. Adv. Synth. Catal. 2018, 360, 4068. doi: 10.1002/adsc.v360.21 pmid: 30958678
	(d) Chen, G.; Zhang, X.; Jia, R.; Li, B.; Fan, X. Adv. Synth. Catal. 2018, 360, 3781. doi: 10.1002/adsc.v360.19 pmid: 30958678
	(e) Wu, X.; Xiao, Y.; Sun, S.; Yu, J. T.; Cheng, J. Org. Lett. 2019, 21, 6653. doi: 10.1021/acs.orglett.9b02249 pmid: 30958678
	(f) Chen, X.; Wang, M.; Zhang, X.; Fan, X. Org. Lett. 2019, 21, 2541. doi: 10.1021/acs.orglett.9b00340 pmid: 30958678
[12]	(a) Shen, Z.; Pi, C.; Wu, Y.; Cui, X. Chin. Chem. Lett. 2019, 30, 1374. doi: 10.1016/j.cclet.2019.01.033
	(b) He, Y.; Pi, C.; Wu, Y.; Cui, X. Chin. Chem. Lett. 2020, 31, 396. doi: 10.1016/j.cclet.2019.09.025
	(c) Li, T.; Yang, Z.; Song, Z.; Chauvin, R.; Cui, X. Org. Lett. 2020, 22, 4078. doi: 10.1021/acs.orglett.0c01139
	(d) Ren, J.; Pi, C.; Wu, Y.; Cui, X. Org. Lett. 2021, 23, 6628. doi: 10.1021/acs.orglett.1c02077
	(e) Ren, J.; Pi, C.; Wu, Y.; Cui, X. Green Chem. 2022, 24, 3017. doi: 10.1039/D1GC04825B
[13]	(a) Genung, N. E.; Wei, L.; Aspnes, G. E. Org. Lett. 2014, 16, 3114. doi: 10.1021/ol5012423
	(b) Kumar, M. R.; Park, A.; Park, N.; Lee, S. Org. Lett. 2011, 13, 3542. doi: 10.1021/ol201409j
[14]	Barday, M.; Janot, C.; Halcovitch, N. R.; Muir, J.; Aïssa, C. Angew. Chem., Int. Ed. 2017, 56, 13117. doi: 10.1002/anie.201706804

Entry	Variation from standard conditions	Yield^b/%
1	None	83
2	Without [Cp*RhCl₂]₂	NR
3	Without AgOTf	NR
4	CpCo(CO)I₂ instead of [CpRhCl₂]₂	NR
5	[CpIrCl₂]₂ instead of [CpRhCl₂]₂	NR
6	[RuCl₂(p-cymene)]₂ instead of [Cp*RhCl₂]₂	NR
7	Pd(OAc)₂ instead of [Cp*RhCl₂]₂	NR
8	AgSbF₆, AgNTf₂, PhCOOAg, Ag₂CO₃, CF₃COOAg, AgBF₄ instead of AgOTf	64/68/56/46/64/70
9	DCE, DCM, CH₃CN, THF, DMF, MeOH, HFIP, toluene instead of TFE	52/48/43/NR/NR/63/45/60
10	PivOH, HOAc, 1-AdCOOH, TsOH instead of PhCOOH	52/63/58/54
11	TFA (1 equiv.)	64
12	80 ℃ instead of 120 ℃	42

Entry	Variation from standard conditions	Yield^b/%
1	None	83
2	Without [Cp*RhCl₂]₂	NR
3	Without AgOTf	NR
4	CpCo(CO)I₂ instead of [CpRhCl₂]₂	NR
5	[CpIrCl₂]₂ instead of [CpRhCl₂]₂	NR
6	[RuCl₂(p-cymene)]₂ instead of [Cp*RhCl₂]₂	NR
7	Pd(OAc)₂ instead of [Cp*RhCl₂]₂	NR
8	AgSbF₆, AgNTf₂, PhCOOAg, Ag₂CO₃, CF₃COOAg, AgBF₄ instead of AgOTf	64/68/56/46/64/70
9	DCE, DCM, CH₃CN, THF, DMF, MeOH, HFIP, toluene instead of TFE	52/48/43/NR/NR/63/45/60
10	PivOH, HOAc, 1-AdCOOH, TsOH instead of PhCOOH	52/63/58/54
11	TFA (1 equiv.)	64
12	80 ℃ instead of 120 ℃	42

[1]	Baochang Gao, Yu Shi, Yuan Tian, Zhiguo Zhang, Jingru Zhang, Yufeng Sun, Guoliang Mao, Lingyan Dai. Synthesis of 4-Methyl-2-oxo-6-arylamino-2H-pyran-3-carbonitrile Derivatives [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 644-649.
[2]	Jing Tang, Wenkun Luo, Jun Zhou. Advances in the Synthesis of Azaspiro[4.5]trienones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3006-3034.
[3]	Yingke Feng, He Wang, Mengxing Cui, Ran Sun, Xin Wang, Yang Chen, Lei Li. Visible-Light-Induced Difluoroalkylated Cyclization of Novel Functionalized Aromatic Isocyanides [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2913-2925.
[4]	Yuzhuo Chen, Hongmei Sun, Liang Wang, Fangzhi Hu, Shuaishuai Li. Research Progress on Construction of Heterocyclic Skeletons Based on α-Hydride Transfer Strategy [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2323-2337.
[5]	Lixing Sun, Tingting Sun, Haiqing Wang, Shufang Wu, Xiaoye Wang, Tianya Liu, Yuchen Zhang. Lewis Acid-Catalyzed [2+4] Cyclization of 3-Alkyl-2-vinylindoles with α,β-Unsaturated N-Sulfonyl Ketimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2178-2188.
[6]	Zhijun Ren, Weiwei Luo, Jun Zhou. Recent Progress in Silver-Mediated Tandem Cyclization of N-Arylacrylamides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2026-2039.
[7]	Rongbin Cai, Bing Li, Qi Zhou, Longyi Zhu, Jun Luo. Synthesis of 4,8,9,10-Tetrafunctionalized 2-Azaadamantanes and Their 2-Azaprotoadamantane Skeleton Isomers [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2217-2225.
[8]	Jingpeng Li, Shuntao Huang, Qi Yang, Weiqiang Li, Teng Liu, Chao Huang. A Practical Synthesis of (Z)-N-Vinyl Substituted N,O-Acetals under Continuous Flow Technology [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1550-1558.
[9]	Nan Jiang, Guanjie Huang, Yan Hu, Bo Wang. Ruthenium-Catalyzed C—H [4＋2] Annulation of Quinazolinones with Vinylene Carbonate [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1537-1549.
[10]	Chunsheng Li, Xiaoqi Lian, Lianfen Chen. Copper-Catalyzed [4＋2] Annulations of Sulfoxonium Ylides and o-Phenylenediamines [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1492-1498.
[11]	Jinxiao Zhao, Tonghui Wei, Sen Ke, Yi Li. Visible Light-Catalyzed Synthesis of Difluoroalkylated Polycyclic Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1102-1114.
[12]	Chengfu Zeng, Yuan He, Qing Li, Lin Dong. Ir(III)-Catalyzed Novel Three-Component Cascade Trifluoroethoxylation and One-Pot Method to Construct Complex Amide Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1115-1123.
[13]	Haiqing Wang, Shuang Yang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 974-999.
[14]	Wenting Wei, Zhuangzhuang Li, Wandi Li, Jiaqi Li, Xianying Shi. Green Method for Constructing Phthalides via Oxidative Coupling of Aromatic Acids and Acrylates in Neat Water and Air [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1177-1186.
[15]	Tian Sang, Fan Jia, Jing He, Chuntian Li, Yan Liu, Ping Liu. I₂-Catalyzed Cyclization of β-Ketonitrile with 1H-Pyrazol-5-amine [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 195-201.

铑催化2-芳基-2H-吲唑与硫叶立德的酰甲基化/串联环化反应高效构建6-芳基吲唑并[2,3-a]喹啉类衍生物

Rhodium-Catalyzed Tandem Acylmethylation/Annulation Reactions of 2-Aryl-2H-indazoles with Sulfoxonium Ylides: Easy Access to 6-Arylindazolo[2,3-a]quinolines

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 6

References 14

Related Articles 15

Recommended Articles

Metrics

Comments