PPh3-Mediated Synthesis of 3-Hydroxy-2-oxindoles from o-Alkynylnitrobenzenes

doi:10.6023/cjoc202304017

Abstract

The 3-hydroxy-2-oxindole core structure is of considerable significance in both synthetic and medicinal chemistry. A novel and efficient base-promoted method for the preparation of 3-hydroxy-2-oxindoles from o-alkynylnitroarenes has been discovered. The reaction could be conducted under transition metal free conditions. Various o-alkynylnitroarenes were checked and the desired products were obtained in moderate to good yields. The Wittig-like reaction triggered by the PPh₃ and the subsequent acyloin rearrangement constituted the main reaction process.

Key words: PPh₃, Wittig reaction, 3-hydroxy-2-oxindoles, o-alkynylnitroarenes

Cite this article

Xuechun Zhao, Hui Fan, Yao Xu, Xiaoming Liao, Xiaoxiang Zhang. PPh₃-Mediated Synthesis of 3-Hydroxy-2-oxindoles from o-Alkynylnitrobenzenes[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3997-4002.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 5

References 19

[1]	(a) Lin, M. J.; Zhu, L.; Xia, J. J.; Yu, Y. H.; Chen, J. X.; Mao, Z. F.; Huang, X. L. Adv. Synth. Catal. 2018, 360, 2280. doi: 10.1002/adsc.v360.12 pmid: 34110644
	(b) Yu, Y. H.; Zhu, L.; Liao, Y.; Mao, Z. F.; Huang, X. L. Adv. Synth. Catal. 2016, 358, 1059. doi: 10.1002/adsc.v358.7 pmid: 34110644
	(c) Kenny, R. T.; Liu, F. Asian J. Org. Chem. 2022, 11. pmid: 34110644
	(d) Ma, L. Y.; Yu, Y. H.; Xin, L. T.; Zhu, L.; Xia, J. J.; Ou, P. C.; Huang, X. L. Adv. Synth. Catal. 2021, 363, 2573. doi: 10.1002/adsc.v363.10 pmid: 34110644
	(e) Day, D. P.; Chan, P. W. H. Adv. Synth. Catal. 2016, 358, 1368. doi: 10.1002/adsc.v358.9 pmid: 34110644
	(f) Jin, J. W.; Zhao, Y. C.; Sze, E. M. L.; Kothandaraman, P.; Chan, P. W. H. Adv. Synth. Catal. 2018, 360, 4744. doi: 10.1002/adsc.v360.24 pmid: 34110644
	(g) Zhao, Y. C.; Henry, S. A.; Jin, J. W.; Clarkson, G. J.; Chan, P. W. H. Asian J. Org. Chem. 2019, 8, 1029. doi: 10.1002/ajoc.v8.7 pmid: 34110644
	(h) Zheng, Y.; Qian, S. C.; Xu, P. C.; Ma, T. T.; Huang, S. L. Adv. Synth. Catal. 2022, 364, 3800. doi: 10.1002/adsc.v364.22 pmid: 34110644
	(i) Meng, X. T.; Xu, H. H.; Liu, R.; Zheng, Y.; Huang, S. L. Green Chem. 2022, 24, 4754. doi: 10.1039/D2GC01129H pmid: 34110644
	(j) Huang, Y.; Chen, D. F.; Zheng, Y.; Huang, S. L. Chemistryselect, 2022, 7. pmid: 34110644
	(k) Song, L. N.; Tian, X. H.; Han, C. Y.; Amanpur, M.; Rominger, F.; Hashmi, A. S. K. Org. Chem. Front. 2021, 8, 3314. doi: 10.1039/D1QO00473E pmid: 34110644
	(l) Greiner, L. C.; Inuki, S.; Arichi, N.; Oishi, S.; Suzuki, R.; Iwai, T.; Sawamura, M.; Hashmi, A. S. K.; Ohno, H. Chem.-Eur. J. 2021, 27, 12992. doi: 10.1002/chem.202101824 pmid: 34110644
	(m) Lustosa, D. M.; Hartmann, D.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Eur. J. Org. Chem. 2020, 2020, 1160. doi: 10.1002/ejoc.v2020.9 pmid: 34110644
	(n) Li, Z. Y.; Wang, N. N.; Liu, J.; Mei, H. B.; Soloshonok, V. A.; Han, J. L. Org. Lett. 2021, 23, 6941. doi: 10.1021/acs.orglett.1c02538 pmid: 34110644
	(o) Xie, L. G.; Shaaban, S.; Chen, X. Y.; Maulide, N. Angew. Chem., Int. Ed. 2016, 55, 12864. doi: 10.1002/anie.v55.41 pmid: 34110644
	(p) Liu, Q. S.; Wang, L. L.; Yue, H. L.; Li, J. S.; Luo, Z. D.; Wei, W. Green Chem. 2019, 21, 1609. doi: 10.1039/C9GC00222G pmid: 34110644
	(q) Sun, J. B.; Miao, T.; Li, P. H.; Wang, L. Chin. J. Org. Chem. 2021, 41, 3144. (in Chinese) doi: 10.6023/cjoc202102025 pmid: 34110644
	(孙佳兵, 苗涛, 李品华, 王磊, 有机化学, 2021, 41, 3144.) doi: 10.6023/cjoc202102025 pmid: 34110644
[2]	(a) Zheng, K.; Yin, C. K.; Liu, X. H.; Lin, L. L.; Feng, X. M. Angew. Chem. Int. Ed. 2011, 50, 2573. doi: 10.1002/anie.201007145 pmid: 21370340
	(b) Pastor, M.; Vayer, M.; Weinstabl, H.; Maulide, N. J. Org. Chem. 2022, 87, 606. doi: 10.1021/acs.joc.1c02616 pmid: 21370340
	(c) Gambacorta, G.; Apperley, D. C.; Baxendale, I. R. Molecules 2020, 25, 2160. doi: 10.3390/molecules25092160 pmid: 21370340
	(d) El-Hussieny, M.; El-Sayed, N. F.; Fouad, M. A.; Ewies, E. F. Bioorg. Chem. 2021, 117, 105421. doi: 10.1016/j.bioorg.2021.105421 pmid: 21370340
	(e) Han, J. S.; Zhang, J. L.; Zhang, W. Q.; Gao, Z. W.; Xu, L. W.; Jian, Y. J. J. Org. Chem. 2019, 84, 7642. doi: 10.1021/acs.joc.9b00441 pmid: 21370340
[3]	(a) Mo, Y. Z.; Zhao, J. P.; Chen, W. P.; Wang, Q. F. Res. Chem. Intermediat. 2015, 41, 5869. doi: 10.1007/s11164-014-1707-5 pmid: 30300974
	(b) Griffiths, B. M.; Burl, J. D.; Wang, X. Synlett 2016, 27, 2039. doi: 10.1055/s-0035-1561638 pmid: 30300974
	(c) Ori, M.; Toda, N.; Takami, K.; Tago, K.; Kogen, H. Tetrahedron 2005, 61, 2075. doi: 10.1016/j.tet.2004.12.041 pmid: 30300974
	(d) Boominathan, S. S. K.; Wang, J. J. Chem.-Eur. J. 2015, 21, 17044. doi: 10.1002/chem.201503210 pmid: 30300974
	(e) Singh, S.; Gajulapati, V.; Gajulapati, K.; Goo, J. I.; Park, Y. H.; Jung, H. Y.; Lee, S. Y.; Choi, J. H.; Kim, Y. K.; Lee, K.; Heo, T. H.; Choi, Y. Bioorg. Med. Chem. Lett. 2016, 26, 1282. doi: 10.1016/j.bmcl.2016.01.016 pmid: 30300974
	(f)Wang, W.; Cencic,R.; L. Whitesell, J. Pelletier, J.; Porco, J. A. Wang, W.; Cencic, R.; L. Whitesell, J. Pelletier, J.; Porco, J. A. Chem.-Eur. J. 2016, 22, 12006 doi: 10.1002/chem.v22.34 pmid: 30300974
	(h) Franke, J.; Kim, J.; Hamilton, J. P.; Zhao, D. Y.; Pham, G. M., Wiegert-Rininger, K.; Crisovan, E.; Newton, L.; Vaillancourt, B.; Tatsis, E.; Buell, C. R.; O'Connor, S. E. ChemBioChem 2019, 20, 83. doi: 10.1002/cbic.201800592 pmid: 30300974
	(i) Khuzhaev, V. U.; Zhalolov, I.; Turgunov, K. K.; Tashkhodzhaev, B.; Levkovich, M. G.; Aripova, S. F.; Shashkov, A. S. Chem. Nat. Compd. 2004, 40, 269. doi: 10.1023/B:CONC.0000039139.30391.2c pmid: 30300974
[4]	(a) De Silva, N. H.; Dahdah, A.; Blanch, E. W.; Huegel, H. M.; Maniam, S. Eur. J. Med. Chem. 2022, 240.
	(b) Kinthada, L. K.; Ghosh, S.; Babu, K. N.; Sharique, M.; Biswas, S.; Bisai, A. Org. Biomol. Chem. 2014, 12, 8152. doi: 10.1039/C4OB01264J
	(c) Seo, D. Y.; Min, B. K.; Roh, H. J.; Kim, J. N. B. Korean Chem. Soc. 2017, 38, 1231. doi: 10.1002/bkcs.2017.38.issue-10
	(d) Chandran, R.; Pise, A.; Shah, S. K.; Rahul, D.; Baluni, A.; Tiwari, K. N. Synth. Commun. 2021, 51, 245. doi: 10.1080/00397911.2020.1822409
	(e) Sohail, M.; Tanaka, F. Chem.-Eur. J. 2020, 26, 222. doi: 10.1002/chem.v26.1
[5]	(a) Kamano, Y.; Zhang, H. P.; Ichihara, Y.; Kizu, H.; Komiyama, K.; Pettit, G. R. Tetrahedron Lett. 1995, 36, 2783.
	(b) Rasmussen, H. B.; MacLeod, J. K. J. Nat. Prod. 1997, 60, 1152. doi: 10.1021/np970246q
	(c) Suchy, M.; Kutschy, P.; Monde, K.; Goto, H.; Harada, N.; Takasugi, M.; Dzurilla, M.; Balentova, E. J. Org. Chem. 2001, 66, 3940. doi: 10.1021/jo0155052
	(d) Tang, Y. Q.; Sattler, I.; Thiericke, R.; Grabley, S.; Feng, X. Z. Eur. J. Org. Chem. 2001, 2001, 261. doi: 10.1002/(ISSN)1099-0690
[6]	(a) Kumar, G. S.; Ramesh, P.; Kumar, A. S.; Swetha, A.; Meshram, H. M. Tetrahedron Lett. 2013, 54, 5048. doi: 10.1016/j.tetlet.2013.07.027
	(b) Zhou, Z. Q.; Xu, Y.; Zhu, B. Y.; Li, P.; Hu, G. W.; Yang, F.; Xu, S. J.; Zhang, X. X. New J. Chem. 2020, 44, 20303. doi: 10.1039/D0NJ04588H
	(c) Liu, D. Y.; Zhao, G. W.; Xiang, L. Eur. J. Org. Chem. 2010, 2010, 3975. doi: 10.1002/ejoc.v2010:21
	(d) Wang, D. S.; Chen, Q. A.; Lu, S. M.; Zhou, Y. G. Chem. Rev. 2012, 112, 2557. doi: 10.1021/cr200328h
	(e) Repka, L. M.; Reisman, S. E. J. Org. Chem. 2013, 78, 12314. doi: 10.1021/jo4017953
	(f) Zhuo, C. X.; Zheng, C.; You, S. L. Acc. Chem. Res. 2014, 47, 2558. doi: 10.1021/ar500167f
	(g) Zi, W. W.; Zuo, Z. W.; Ma, D. W. Acc. Chem. Res. 2015, 48, 702. doi: 10.1021/ar5004303
	(h) Roche, S. P.; Tendoung, J. J. Y.; Treguier, B. Tetrahedron 2015, 71, 3549. doi: 10.1016/j.tet.2014.06.054
	(i) Wang, Y. S.; Xie, F. K.; Lin, B.; Cheng, M. S.; Liu, Y. X. Chem.- Eur. J. 2018, 24, 14302. doi: 10.1002/chem.v24.54
	(j) Huang, G. H.; Yin, B. L. Adv. Synth. Catal. 2019, 361, 405. doi: 10.1002/adsc.v361.3
	(k) Silva, T. S.; Rodrigues, M. T.; Santos, H.; Zeoly, L. A.; Almeida, W. P.; Barcelos, R. C.; Gomes, R. C.; Fernandes, F. S.; Coelho, F. Tetrahedron 2019, 75, 2063. doi: 10.1016/j.tet.2019.02.006
[7]	(a) Peris, G.; Vedejs, E. J. Org. Chem. 2015, 80, 3050. doi: 10.1021/jo502939a pmid: 26695735
	(b) Nakazaki, A.; Mori, A.; Kobayashi, S.; Nishikawa, T. Tetrahedron Lett. 2012, 53, 7131. doi: 10.1016/j.tetlet.2012.10.092 pmid: 26695735
	(c) Ulikowski, A.; Furman, B. Org. Lett. 2016, 18, 149. doi: 10.1021/acs.orglett.5b03449 pmid: 26695735
	(d) Tokunaga, T.; Hume, W. E.; Nagamine, J.; Kawamura, T.; Taiji, M.; Nagata, R. Bioorg. Med. Chem. Lett. 2005, 15, 1789. doi: 10.1016/j.bmcl.2005.02.042 pmid: 26695735
[8]	(a) Nasim, A.; Thomas, G. T.; Ovens, J. S.; Newman, S. G. Org. Lett. 2022, 24, 7232. doi: 10.1021/acs.orglett.2c03042
	(b) Kise, N.; Sasaki, K.; Sakurai, T. Tetrahedron, 2014, 70, 9668. doi: 10.1016/j.tet.2014.10.071
	(c) Mandal, T.; Jana, S.; Dash, J. Eur. J. Org. Chem. 2017, 2017, 4972. doi: 10.1002/ejoc.v2017.33
	(d) Reddy, G. S.; Hossain, K. A.; Kumar, J. S.; Thirupataiah, B.; Edwin, R. K.; Giliyaru, V. B.; Hariharapura, R. C.; Shenoy, G. G.; Misra, P.; Pal, M. RSC Adv. 2020, 10, 289. doi: 10.1039/C9RA09236F
[9]	(a) Kaur, J.; Kumar, A.; Chimni, S. S., Tetrahedron Lett. 2014, 55, 2138. doi: 10.1016/j.tetlet.2014.02.054
	(b) Hanhan, N. V.; Sahin, A. H.; Chang, T. W.; Fettinger, J. C.; Franz, A. K. Angew. Chem. Int. Ed. 2010, 49, 744.
	(c) Ramachary, D. B.; Reddy, G. B.; Mondal, R. Tetrahedron Lett. 2007, 48, 7618. doi: 10.1016/j.tetlet.2007.08.129
	(d) Nicolaou, K. C.; Rao, P. B.; Hao, J. L.; Reddy, M. V.; Rassias, G.; Huang, X. H.; Chen, D. Y. K.; Snyder, S. A. Angew. Chem., Int. Ed. 2003, 42, 1753. doi: 10.1002/anie.v42:15
	(e) Zhang, J. W.; Wu, H.; Zhang, W. X.; Wang, L. M.; Jin, Y. Chin. J. Org. Chem. 2021, 41, 1187. (in Chinese) doi: 10.6023/cjoc202009023
	(张俊伟, 吴昊, 张伟鑫, 王黎明, 金瑛, 有机化学, 2021, 41, 1187.) doi: 10.6023/cjoc202009023
[10]	(a) Wei, W. T.; Zhu, W. M.; Shao, Q. J.; Bao, W. H.; Chen, W. T.; Chen, G. P.; Luo, Y. J.; Liang, H. Z. ACS Sustainable Chem. Eng. 2018, 6, 8029. doi: 10.1021/acssuschemeng.8b01472
	(b) Ohmatsu, K.; Ando, Y.; Ooi, T. Synlett 2017, 28, 1291. doi: 10.1055/s-0036-1558958
	(c) Ying, W. W.; Zhu, W. M.; Gao, Z. H.; Liang, H. Z.; Wei, W. T. Synlett 2018, 29, 663. doi: 10.1055/s-0036-1591520
[11]	(a) Shin, I.; Ramgren, S. D.; Krische, M. J. Tetrahedron 2015, 71, 5776. doi: 10.1016/j.tet.2015.05.085 pmid: 21957865
	(b) Shirai, T.; Yamamoto, Y. Organometallics 2015, 34, 3459. doi: 10.1021/om501260w pmid: 21957865
	(c) Shirai, T.; Ito, H.; Yamamoto, Y. Angew. Chem., Int. Ed. 2014, 53, 2658. doi: 10.1002/anie.v53.10 pmid: 21957865
	(d) He, J. Q.; Chen, C.; Yu, W. B.; Liu, R. R.; Xu, M.; Li, Y. J.; Gao, J. R.; Jia, Y. X. Tetrahedron Lett. 2014, 55, 2805. doi: 10.1016/j.tetlet.2014.03.069 pmid: 21957865
	(e) Li, Y.; Zhu, D. X.; Xu, M. H. Chem. Commun. 2013, 49, 11659. doi: 10.1039/c3cc47927g pmid: 21957865
	(f) Hu, J. X.; Wu, H.; Li, C. Y.; Sheng, W. J.; Jia, Y. X.; Gao, J. R. Chem.-Eur. J. 2011, 17, 5234. doi: 10.1002/chem.v17.19 pmid: 21957865
	(g) Gorokhovik, I.; Neuville, L.; Zhu, J. P. Org. Lett. 2011, 13, 5536. doi: 10.1021/ol202263a pmid: 21957865
	(h) Jia, Y. X.; Katayev, D.; Kundig, E. P. Chem. Commun. 2010, 46, 130. doi: 10.1039/B917958E pmid: 21957865
[12]	Zhao, Y. W.; Zhu, H. R.; Sung, S. Y.; Wink, D. J.; Zadrozny, J. M.; Driver, T. G. Angew. Chem., Int. Ed. 2021, 60, 19207. doi: 10.1002/anie.v60.35
[13]	Aksenov, A. V.; Aleksandrova, E. V.; Aksenov, D. A.; Aksenova, A. A.; Aksenov, N. A.; Nobi, M. A.; Rubin, M. J. Org. Chem. 2022, 87, 1434. doi: 10.1021/acs.joc.1c02753
[14]	(a) Fan, H.; Xu, Y.; Yang, F.; Xu, S. J.; Zhao, X. C.; Zhang, X. X. Adv. Synth. Catal. 2022, 364, 2358. doi: 10.1002/adsc.v364.14
	(b) Xu, Y.; Fan, H.; Yang, F.; Xu, S. J.; Zhao, X. C.; Liao, X. M.; Zhang, X. X. J. Org. Chem. 2023, 88, 2801. doi: 10.1021/acs.joc.2c02434
[15]	Mei, H.; Wang, N.; Li, Z.; Han, J. Org. Lett. 2022, 24, 2258. doi: 10.1021/acs.orglett.2c00738
[16]	Wetzel, A.; Gagosz, F. Angew. Chem., Int. Ed. 2011, 50, 7354. doi: 10.1002/anie.v50.32
[17]	Bumagin, N. A.; Sukhomlinova, L. I.; Luzikova, E. V.; Tolstaya, T. P.; Beletskaya, I. P. Tetrahedron Lett. 1996, 37, 897. doi: 10.1016/0040-4039(95)02255-4
[18]	Xiao, Z. K.; Yin, H. Y.; Shao, L. X. Org. Lett. 2013, 15, 1254. doi: 10.1021/ol400186b
[19]	Chaudhari, M. B.; Sutar, Y.; Malpathak, S.; Hazra, A.; Gnana- prakasam, B. Org. Lett. 2017, 19, 3628. doi: 10.1021/acs.orglett.7b01616

Entry	Base/equiv.	Solvent	PPh₃/equiv.	T/℃	Yield^b/%
1	NaOH (1)	1,4-Dioxane	5	90	65
2	NaOH (3)	1,4-Dioxane	5	90	75
3	NaOH (5)	1,4-Dioxane	5	90	77
4	NaOH (3)	CH₃CN	5	90	82
5	NaOH (3)	DMF	5	90	N.D.^c
6	NaOH (3)	DMSO	5	90	N.D.^c
7	NaOH (3)	Toluene	5	90	22
8	NaOH (3)	EtOH	5	90	52
9	NaOH (3)	THF	5	90	35
10	Cs₂CO₃ (3)	CH₃CN	5	90	70
11	K₂CO₃ (3)	CH₃CN	5	90	69
12	DBU (3)	CH₃CN	5	90	43
13	—	CH₃CN	5	90	N.D.^c
14	NaOH (3)	CH₃CN	3	90	61
15	NaOH (3)	CH₃CN	5	50	45
16	NaOH (3)	CH₃CN	5	90	13^d
17	NaOH (3)	CH₃CN	5	90	76^e

Entry	Base/equiv.	Solvent	PPh₃/equiv.	T/℃	Yield^b/%
1	NaOH (1)	1,4-Dioxane	5	90	65
2	NaOH (3)	1,4-Dioxane	5	90	75
3	NaOH (5)	1,4-Dioxane	5	90	77
4	NaOH (3)	CH₃CN	5	90	82
5	NaOH (3)	DMF	5	90	N.D.^c
6	NaOH (3)	DMSO	5	90	N.D.^c
7	NaOH (3)	Toluene	5	90	22
8	NaOH (3)	EtOH	5	90	52
9	NaOH (3)	THF	5	90	35
10	Cs₂CO₃ (3)	CH₃CN	5	90	70
11	K₂CO₃ (3)	CH₃CN	5	90	69
12	DBU (3)	CH₃CN	5	90	43
13	—	CH₃CN	5	90	N.D.^c
14	NaOH (3)	CH₃CN	3	90	61
15	NaOH (3)	CH₃CN	5	50	45
16	NaOH (3)	CH₃CN	5	90	13^d
17	NaOH (3)	CH₃CN	5	90	76^e

PPh₃-促进邻炔基硝基苯合成3-羟基-2-吲哚酮

PPh₃-Mediated Synthesis of 3-Hydroxy-2-oxindoles from o-Alkynylnitrobenzenes

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 5

References 19

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Hai Xie, Yali Zhang, Xiuting Qin, Yongxin Gu. Synthesis of 1,2,4-Trisubstituted Imidazoles via Sequential Staudinger/aza-Wittig/Aromatization Reaction [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 525-532.
[2]	Chujie Liao, Hongyao Ruan, Junfeng Jiang, Lun Luo, Yanggen Hu. Synthesis and Activity Evaluation of 3-Aryl-2-imino-benzo[e][1,3]-oxazin-4-ol Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 763-770.
[3]	Long Zhao, Maolin Yang, Haoran Chen, Mingwu Ding. One-Pot Three-Component Synthesis of 3,4-Dihydroquinazoline Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3740-3746.
[4]	Jinni Liu, Yibi Xie, Qingqing Yang, Nianyu Huang, Long Wang. Ugi Four-Component Reaction Based on the in situ Capture of Amines and Subsequent Modification Tandem Cyclization Reaction: "One-Pot" Synthesis of Six- and Seven-Membered Heterocycles [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2374-2383.
[5]	Hongyan Shi, Ying Zhong, Zhigang Zhao. Synthesis of Multi-substituted 1,4-Dihydroquinoline Derivatives from Morita-Baylis-Hillman (MBH) Carbonates [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 677-687.
[6]	Wei Cai, You Huang. Advances in Organophosphorus Redox Catalysis [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3903-3913.
[7]	Zhao Zhuanxia, Wang Junjiao, Huang Danfeng, Yang Zheng, Zhao Fangxia, Hu Yongqin, Xu Weigang, Hu Yulai. Study on Tin Powder-Promoted Allylation of 3-Aryl-3-hydroxy-2-oxindoles [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2026-2034.
[8]	Zhang Jingjing, Yao Ming, Li Li, Sang Dayong, Xiong Hangxing, Liu Shengpeng. Synthesis of Resveratrol, Piceatannol and Pinosylvin [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 1062-1067.
[9]	Su Yingpeng, Feng Yawei, Cao Lindan, Xue Wenxuan, Shi Ya, Chang Bingbing, Huang Danfeng, Wang Ke-Hu, Hu Yulai. Triphenylphosphine Catalyzed Lu's[3+2] Annulation of Aurones and Alkenoates: Constructing of Spiro[1-benzofuran-3-one-2,5'-cyclopentene] Polycyclic Compounds [J]. Chin. J. Org. Chem., 2019, 39(5): 1333-1343.
[10]	Wu Jing, Kong Hanhan, Ding Mingwu. Synthesis of 12H,14H-Quinazolino[3,4-a]-3,1-benzoxazines [J]. Chin. J. Org. Chem., 2016, 36(7): 1662-1667.
[11]	Zou Wen, He Zheng-Rong, He Zhengjie. A Facile and New Synthetic Method of Polysubstituted Furans [J]. Chin. J. Org. Chem., 2015, 35(8): 1739-1745.
[12]	Wang Hongmei, Guo Shubing, Hu Yanggen, Zeng Xiaohua, Yang Guangyi. Synthesis and Antitumor Activity of Some Novel 5,6,7,8-Tetrahydro- benzo-thieno[2,3-d]pyrimidin-4(3H)-one Derivatives [J]. Chin. J. Org. Chem., 2015, 35(5): 1075-1080.
[13]	Wang Yazhen, Zhu Xingxing, Lin Wei, Zheng Chunzhi, Zhang Jizhen. A Novel Synthetic Method of 3-Methyleneisobenfuran- 1(3H)-one and Their Derivatives [J]. Chin. J. Org. Chem., 2015, 35(11): 2412-2419.
[14]	Zheng Chunzhi, Zhu Xingxing, Zhao Dejian, Jia Hongbin, Zhang Jizhen. Synthesis of 3-Alkylidene(arylidene)isobenfuran-1(3H)-one and Their Derivatives [J]. Chin. J. Org. Chem., 2014, 34(9): 1881-1888.
[15]	Yang Xiaomei, Zhang Yushun, Yao Yun, Tao Yunhai. Simple Synthesis of (Z)-7-Eicosen-11-one- the Sex Pheromone of Peach Fruit Moth [J]. Chin. J. Org. Chem., 2014, 34(7): 1458-1461.

PPh3-促进邻炔基硝基苯合成3-羟基-2-吲哚酮