基于原位捕获异腈的Ugi四组分反应及其后修饰串联反应: 一锅法合成含氮杂环化合物

doi:10.6023/cjoc202108030

摘要/Abstract

报道了一种基于原位捕获异腈的Ugi四组分反应及后修饰串联反应的新策略. 根据该反应策略, 异腈化物被原位制备, 并立即被捕获参与Ugi四组分反应及后续的修饰串联反应. 相比之前的报道, 该策略在Ugi四组分反应及其后修饰串联反应中实现了基于异腈的原位捕获, 解决了反应中异腈化物的不稳定、高毒性和对环境的不友好等问题. 温和的反应条件, 精简的制备方法, 也为异腈参与的Ugi四组分及后修饰串联反应提供了一种绿色无污染的新策略.

关键词: 异腈的原位捕获, Ugi四组分反应, 后修饰串联反应, 绿色异腈化学, 一锅法合成

A novel strategy of Ugi four-component and post-modification tandem reaction based on in-situ capture of isocyanide is reported in this paper. According to this reaction strategy, the isocyanide was prepared in situ and immediately captured to participate in Ugi four-component reaction and the subsequent modification tandem reaction. Compared with the previous reports, based on in-situ capture of isocyanide was realized in the Ugi four-component reaction and post-modification tandem reaction, which solved the problems of isocyanide instability, high toxicity and unfriendly to the environment in the reaction. Mild reaction system conditions and simplified preparation method provide a novel green and pollution-free strategy for the tandem reaction of Ugi four-component and post modification series reaction with isocyanide.

Key words: in-situ capture of isocyanide, Ugi four-component reaction, post-modification tandem reaction, green isocyanide chemistry, one-pot synthesis

引用此文

罗享豪, 谢益碧, 黄年玉, 王龙. 基于原位捕获异腈的Ugi四组分反应及其后修饰串联反应: 一锅法合成含氮杂环化合物[J]. 有机化学, 2022, 42(3): 838-846.

Xianghao Luo, Yibi Xie, Nianyu Huang, Long Wang. Ugi Four-Component Reaction Based on in-situ Capture of Isocyanide and Post-Modification Tandem Reaction: One-Pot Synthesis of Nitrogen Heterocycles[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 838-846.

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图/表 6

图式1. 基于原位捕获异腈的连续的Ugi-4CR/Staudinger/aza-Witting反应合成策略

Scheme 1. Reaction strategy of Ugi-4CR/Staudinger/aza-Witting reaction based on in-situ capture of isocyanides

Entry	Solvent	PR₃	Temp./℃	Yield^b/%
1	CH₂Cl₂	PPh₃	r.t.	61
2	CH₂Cl₂	PPh₃	45	84
3	CH₂Cl₂	PPh₃	45	67
4	CH₂Cl₂	PMePh₂	45	63
5	Toluene	PPh₃	45	78
6	THF	PPh₃	45	45
7	CH₃OH	PPh₃	45	29
8	DMSO	PPh₃	45	0

表1. 反应条件优化a

Table 1. Optimization of the reaction conditions

表2. 合成5-氧代-4,5-二氢-3H-苯并[e][1,4]二氮杂?类化合物5的底物拓展a

Table 2. Substrate expansion for the synthesis of 5-oxo-4,5- dihydro-3H-benzo[e][1,4]diazepines 5

表3. 通过Ugi-4CR/Wittig串联反应制备1-氧代-2,3-二氢-1H-苯并[c]氮杂?类化合物a

Table 3. Preparation of 1-oxo-2,3-dihydro-1H-benzo[c]azepine 7 by the Ugi-4CR/Wittig tandem reac-tion

图式2. 条件控制实验

Scheme 2. Condition control experiment

图式3. 可能的化学反应机理

Scheme 3. Proposed possible mechanism

参考文献 14

[1]	(a) Ugi, I.; Dömling, A.; Hörl, W. Endeavour 1994, 18, 115.
	(b) Dömling, A. Chem. Rev. 2006, 106, 17. doi: 10.1021/cr0505728
	(c) Domling, A.; Wang, W.; Wang, K. Chem. Rev. 2012, 112, 3083. doi: 10.1021/cr100233r
	(d) de Graaff, C.; Ruijter, E.; Orru, R. V. A. Chem. Soc. Rev. 2012, 41, 3969. doi: 10.1039/c2cs15361k
	(e) Sharma, U. K.; Sharma, N.; Vachhani, D. D.; Van der Eycken, E. V. Chem. Soc. Rev. 2015, 44, 1836. doi: 10.1039/C4CS00253A
	(f) Zarganes-Tzitzikas, T; Chandgude, A. L.; Dömling, A. Chem. Rec. 2015, 15, 981. doi: 10.1002/tcr.v15.5
	(g) Shen, C.; Wu, X.-F. Chem.-Eur. J. 2017, 23, 2973. doi: 10.1002/chem.201603623
	(h) Neochoritis, C. G.; Zhao, T., Dömling, A. Chem. Rev. 2019, 119, 1970. doi: 10.1021/acs.chemrev.8b00564
	(i) Shi, Y.; Qin, Fu.-W.; Wang, J.; Yan, Y.-M. Chin. J. Org. Chem. 2021, 41, 297. (in Chinese) doi: 10.6023/cjoc202005029
	(石瑛, 秦富文, 王捷, 闫艳梅, 有机化学, 2021, 41, 297.)
	(j) Zhu, J. P.; Bienaymé, H. In Multicomponent Reactions, Verlag GmbH & Co. KGaA, Weinheim, 2005, pp. 1-94.
[2]	(a) Dömling, A., Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168. doi: 10.1002/(ISSN)1521-3773 pmid: 29238790
	(b) Kusebauch, U.; Beck, B.; Messer, K.; Herdtweck, E.; Domling, A. Org. Lett. 2003, 5, 4021. pmid: 29238790
	(c) Jiang, B.; Rajale, T.; Wever, W.; Tu, S.-J.; Li, G. Chem. Asian J. 2010, 5, 2318. doi: 10.1002/asia.v5:11 pmid: 29238790
	(d) Rotstein, B. H.; Zaretsky, S.; Rai, V.; Yudin, A. K. Chem. Rev. 2014, 114, 8323. doi: 10.1021/cr400615v pmid: 29238790
	(e) Cioc, R. C.; Ruijter, E.; Orru, R. V. A. Green Chem. 2014, 16, 2958. doi: 10.1039/C4GC00013G pmid: 29238790
	(f) Ibarra, I. A.; Islas-Jácome, A.; González-Zamora, E Org. Biomol. Chem. 2018, 16, 1402. doi: 10.1039/c7ob02305g pmid: 29238790
	(g) Zhang, Z.; You, Y.-Z., Hong, C.-Y. Macromol. Rapid Commun. 2018, 39, 1800362. doi: 10.1002/marc.v39.23 pmid: 29238790
	(h) Zhi, S.-J.; Ma, X.-M.; Zhang, W. Org. Biomol. Chem. 2019, 17, 7632. doi: 10.1039/C9OB00772E pmid: 29238790
	(i) Zhu, J. P.; Wang, Q.; Wang, M. X. In Multicomponent Reactions in Organic Synthesis, Verlag GmbH & Co. KGaA, Weinheim, 2014, pp. 158-182. pmid: 29238790
	(j) Orru, R. V. A; Ruijter, E. In Synthesis of Heterocycles via Multicomponent Reactions I, Springer-Verlag, Berlin Heidelberg, 2010, pp. 199-226. pmid: 29238790
[3]	(a) Andreana, P. R.; Liu, C.-C.; Schreiber, S. L. Org. Lett. 2004, 6, 4231. pmid: 27978705
	(b) El Kaim, L.; Gizolme, M.; Grimaud, L. Org. Lett. 2006, 8, 5021. doi: 10.1021/ol0617502 pmid: 27978705
	(c) Kreye, O.; Tóth, T.; Meier, M. A. R. J. Am. Chem. Soc. 2011, 133, 1790. doi: 10.1021/ja1113003 pmid: 27978705
	(d) Reza Kazemizadeh, A. Curr. Org. Chem. 2012, 16, 418. doi: 10.2174/138527212799499868 pmid: 27978705
	(e) Solleder, S. C.; Meier, M. A. R. Angew. Chem., nt. Ed. 2014, 53, 711. pmid: 27978705
	(f) Chandgude, A. L.; Dömling, A. Org. Lett. 2016, 18, 6396. pmid: 27978705
	(g) Zhang, J.-H.; Niu, L.-Z.; Li, Y.; Liu, S.; Jiang, L. Chin. J. Org. Chem. 2018, 38, 1842. (in Chinese) doi: 10.6023/cjoc201801019 pmid: 27978705
	(张君辉, 牛李智, 李映, 刘思, 姜林, 有机化学, 2018, 38, 1842.) doi: 10.6023/cjoc201801019 pmid: 27978705
	(h) Moni, L.; Banfi, L.; Cartagenova, D.; Cavalli, A.; Lambruschini, C.; Martino, E.; Orru, R. V. A; Ruijter, E.; Saya, J. M.; Sgrignani, J.; Riva, R. Org. Chem. Front. 2020, 7, 380. doi: 10.1039/C9QO00773C pmid: 27978705
[4]	(a) Ugi, I.; Demharter, A.; Hörl, W.; Schmid, T. Tetrahedron 1996, 52, 11657. doi: 10.1016/0040-4020(96)00647-3 pmid: 32574488
	(b) Pan, S.; C. List, B. Angew. Chem., nt. Ed, 2008, 47, 3622. pmid: 32574488
	(c) Vercillo, O. E.; Andrade, C. K. Z.; Wessjohann, L. A. Org. Lett. 2008, 10, 205. pmid: 32574488
	(d) Riva, R. Science 2018, 361, 1072. doi: 10.1126/science.aau7497 pmid: 32574488
	(e) Wang, Q.; Wang, D.-X.; Wang, M.-X.; Zhu, J.-P. Acc. Chem. Res. 2018, 51, 1290. doi: 10.1021/acs.accounts.8b00105 pmid: 32574488
	(f) Nazeri, M. T.; Farhid, H.; Mohammadian, R.; Shaabani, A. ACS Comb. Sci. 2020, 22, 361. doi: 10.1021/acscombsci.0c00046 pmid: 32574488
	(g) Nazeri, M. T.; Nowee, A. B.; Shaabani, A. New J. Chem. 2021, 45, 3479. doi: 10.1039/D0NJ05878E pmid: 32574488
	(h) Guo, X.-Y.; Fang, S.-J.; Qian, H.-F.; Feng, G.-F. Chin. J. Org. Chem. 2021, 41, 1703. (in Chinese) doi: 10.6023/cjoc202010033 pmid: 32574488
	(郭小燕, 方帅军, 钱红飞, 冯高峰, 有机化学, 2021, 41, 1703.) doi: 10.6023/cjoc202010033 pmid: 32574488
	(i) Hu, H. L.; L, A. N.; Z, H. J.; S, D. Q. Chin. J. Org. Chem. 2015, 35, 2162. (in Chinese) doi: 10.6023/cjoc201507003 pmid: 32574488
	(胡汉宁, 黎安玲, 张瀚匀, 石德清, 有机化学, 2015, 35, 2162.) doi: 10.6023/cjoc201507003 pmid: 32574488
[5]	(a) He, P.; Nie, Y. B.; Wu, J, Ding, M.-W. Org. Biomol. Chem. 2011, 9, 1429. doi: 10.1039/c0ob00855a pmid: 25607886
	(b) Tron, G. C. Eur. J. Org. Chem. 2013, 2013, 1849. doi: 10.1002/ejoc.201201660 pmid: 25607886
	(c) Welsch, S. J.; Umkehrer, M.; Kalinski, C, Ross, G.; Burdack, C.; Kolb, J.; Wild, M.; Ehrlich, A.; Wessjohann, L. A. Tetrahedron Lett. 2015, 56, 1025. pmid: 25607886
	(d) Pertejo, P.; Corres, N.; Torroba, T.; Garcia-Valverde, M. Org. Lett. 2015, 17, 612. doi: 10.1021/ol503628r pmid: 25607886
	(e) Xie, H.; Liu, J. C.; Ding, M.-W. Synthesis 2016, 48, 4541. doi: 10.1055/s-0036-1588308 pmid: 25607886
	(f) Snieckus, V.; Board, J. Synfacts 2017, 13, 0241. doi: 10.1055/s-0036-1590028 pmid: 25607886
	(g) Xiong, J.; Wei, X.; Yan, Y.-M.; Ding, M.-W. Tetrahedron 2017, 73, 5720. doi: 10.1016/j.tet.2017.08.011 pmid: 25607886
	(h) Gu, Z. Y.; Ji, S. J. Acta Chim. Sinica. 2018, 76, 347. (in Chinese) doi: 10.6023/A18010023 pmid: 25607886
	(顾正阳, 纪顺俊, 化学学报, 2018, 76, 347.) doi: 10.6023/A18010023 pmid: 25607886
	(i) Xiong, J.; Wei, X.; Wan, Y. C.; Ding, M.-W. Tetrahedron 2019, 75, 1072. doi: 10.1016/j.tet.2019.01.014 pmid: 25607886
	(j) Wang, L.; Guan, Z. R.; Ding, M.-W. Org. Biomol. Chem. 2016, 14, 2413. doi: 10.1039/C5OB02405F pmid: 25607886
[6]	(a) Stigter, E. A.; Guo, Z.; Bon, R. S.; Wu, Y.-W. Choidas, A.; Wolf, A.; Menninger, S.; Waldmann, H.; Blankenfeldt, W.; Goody, R. S. J. Med. Chem. 2012, 55, 8330. doi: 10.1021/jm300624s pmid: 22963166
	(b) Vodela, S.; Mekala, R. V. R. Danda, R. R.; Kodhati, V. Chin Chem. Lett. 2013, 24, 625. doi: 10.1016/j.cclet.2013.04.005 pmid: 22963166
	(c) Zhan, Y.-Z.; Wang, B.-L.; Zhang, L.-Y.; Zhang, Y.; Zhang, Xiao.; Li, Z.-M.; Song, H.-B. Acta Chim. Sinica. 2015, 73, 1173. (in Chinese) doi: 10.6023/A15050333 pmid: 22963166
	(詹益周, 王宝雷, 张丽媛, 张燕, 张晓, 李正名, 宋海斌, 化学学报, 2015, 73, 1173.) doi: 10.6023/A15050333 pmid: 22963166
	(d) Doyle, K.; Lonn, H.; Kack, H.; Van de Poel, A.; Swallow, S.; Gardiner, P.; Connolly, S.; Root, J.; Wikell, C.; Dahl, G.; Stenvall, K.; Johannesson, P. J. Med. Chem. 2016, 59, 9457. doi: 10.1021/acs.jmedchem.6b01127 pmid: 22963166
	(e) Jadhav, A. A.; Dhanwe, V. P.; Joshi, P. G.; Khanna, P. K. Cogent Chem. 2016, 2, 1144670. doi: 10.1080/23312009.2016.1144670 pmid: 22963166
	(f) Mor, S.; Nagoria, S.; Sindhu, S.; Khatri, M.; Sidhu, G.; Singh, V. J. Heterocycl. Chem. 2017, 54, 3282. doi: 10.1002/jhet.v54.6 pmid: 22963166
	(g) Erol, M.; Celik, I.; Temiz-Arpaci, O.; Kaynak-Onurdag, F.; Okten, S. J. Biomol. Struct. Dyn. 2021, 39, 3080. pmid: 22963166
[7]	(a) Costantino, L.; Barlocco, D. Curr. Med. Chem. 2006, 13, 65. pmid: 18855614
	(b) Mandrioli, R.; Mercolini, L.; Raggi, M. A. Curr. Drug Metab. 2008, 9, 827. pmid: 18855614
	(c) Demmer, C. S.; Bunch, L. Eur. J. Org. Chem. 2015, 97, 778. pmid: 18855614
	(d) Kvasnica, M.; Urban, M.; Dickinson, N.; J.; Sarek, J. Nat. Prod. Rep. 2015, 32, 1303. doi: 10.1039/C5NP00015G pmid: 18855614
	(e) Norwood IV, V. M.; Huigens III, R. W. ChemBioChem 2019, 20, 2273. doi: 10.1002/cbic.v20.18 pmid: 18855614
	(f) Pathania, S.; Narang, R. K.; Rawal, R. K. Eur. J. Org. Chem. 2019, 180, 486. pmid: 18855614
	(g) Li, Y.-Y.; Zhou, M.-B.; Xu, L. Zhou, B.-X.; Rao, Y.-T.; Nie, H.; Gu, T.-T.; Zhou, J.; Liang, X.; Yin, B. S.; Zhu, W.-H.; Osuka, A.; Song, J.-X. Org. Lett. 2020, 22, 6001. doi: 10.1021/acs.orglett.0c02084 pmid: 18855614
	(h) Ashton, H. Curr. Opin. Psychiatry 2005, 18, 249. doi: 10.1097/01.yco.0000165594.60434.84 pmid: 18855614
	(i) Votaw, V. R.; Geyer, R.; Rieselbach, M. M.; McHugh, R. K. Drug Alcohol Depen. 2019, 200, 95. doi: 10.1016/j.drugalcdep.2019.02.033 pmid: 18855614
	(j) Wang, Y.. Ph.D. Dissertation, Central China Normal University, Wuhan, 2014. (in Chinese) pmid: 18855614
	(王英, 博士论文, 华中师范大学, 武汉, 2014.) pmid: 18855614
	(k) Wang, L. Ph.D. Dissertation, Central China Normal University, Wuhan, 2015. (in Chinese) pmid: 18855614
	(王龙, 博士论文, 华中师范大学, 武汉, 2015.) pmid: 18855614
[8]	(a) Nishikawa, T.; Urabe, D.; Tomita, M.; Tsujimoto, T.; Iwabuchi, T.; Isobe, M. Org. Lett. 2006, 8, 3263. pmid: 16836381
	(b) El Kaim, L.; Grimaud, L.; Schiltz, A. Org. Biomol. Chem. 2009, 7, 3024. doi: 10.1039/b908541f pmid: 16836381
	(c) El Kaim, L.; Grimaud, L.; Schiltz, A. Tetrahedron Lett. 2009, 50, 5235. doi: 10.1016/j.tetlet.2009.07.001 pmid: 16836381
	(d) Sharma, S.; Maurya, R. A.; Min, K. I.; Jeong, G. Y.; Kim, D. P. Angew. Chem., nt. Ed. 2013, 52, 7564. pmid: 16836381
	(e) Rostamnia, S. RSC Adv. 2015, 5, 97044. doi: 10.1039/C5RA20455K pmid: 16836381
	(f) Neochoritis, C. G.; Stotani, S.; Mishra, B.; Dömling, A. Org. Lett. 2015, 17, 2002. doi: 10.1021/acs.orglett.5b00759 pmid: 16836381
	(g) Muthukumar, A.; Mamillapalli, N. C.; Sekar, G. Adv. Synth. Catal. 2016, 358, 643. doi: 10.1002/adsc.201500815 pmid: 16836381
[9]	Fédou, N. M.; Parsons, P. J.; Viseux, E. M. E.; Whittle, A. J. Org. Lett. 2005, 7, 3179. doi: 10.1021/ol050892d
[10]	Kruithof, A.; Ruijter, E.; Orru, R. V. A. Chem. Asian J. 2015, 10, 508. doi: 10.1002/asia.201403207
[11]	Wang, Y.; Zhou, Y.; Song, Q. Chem. Commun. 2020, 56, 6106. doi: 10.1039/D0CC01919D
[12]	(a) Liu, N.; Chao, F.; Liu, M. G.; Huang, N. Y.; Zou, K.; Wang, L. J. Org. Chem. 2019, 84, 2366. doi: 10.1021/acs.joc.8b03242 pmid: 30676019
	(b) Liu, M. G.; Liu, N.; Xu, W. H.; Wang, L. Tetrahedron 2019, 75, 2748. doi: 10.1016/j.tet.2019.03.057 pmid: 30676019
[13]	(a) Wang, L.; Xie, Y. B.; Huang, N. Y.; Yan, J. Y.; Hu, W. M.; Liu, M. G.; Ding, M. W. ACS Catal. 2016, 6, 4010. doi: 10.1021/acscatal.6b00165
	(b) Wang, L.; Xie, Y. B.; Huang, N. Y.; Zhang, N. N.; Li, D. J.; Hu, Y. L.; Liu, M. G.; Li, D. S. Adv. Synth. Catal. 2017, 359, 779. doi: 10.1002/adsc.v359.5
	(c) Liu, J.; Xie, Y.; Yang, Q.; Huang, N.; Wang, L. Chin. J. Org. Chem. 2021, 41, 2374. (in Chinese) doi: 10.6023/cjoc202012040
	(刘金妮, 谢益碧, 阳青青, 黄年玉, 王龙, 有机化学, 2021, 41, 2374.) doi: 10.6023/cjoc202012040
	(d) Liu, J. N.; Liu, N.; Yang, Q. Q.; Wang, L. Org. Chem. Front. 2021, 8, 5296. doi: 10.1039/D1QO00777G
	(e) Tian, A. Q.; Luo, X. H.; Ren, Z. L.; Zhao, J.; Wang, L. New J. Chem. 2021, 45, 9614. doi: 10.1039/D1NJ00861G
	(f) Zhu, G. X.; Zhao, J. X.; Duan, T. B.; Wang, L.; Wang, D. W. Asian J. Org. Chem. 2021, 10, 2213. doi: 10.1002/ajoc.v10.8
	(g) Yang, Q. Q.; Liu, N.; Yan, J. Y.; Ren, Z. L.; Wang, L. Asian J. Org. Chem. 2020, 9, 116. doi: 10.1002/ajoc.v9.1
	(h) Ren, Z. L.; Cai, S.; Liu, Y. Y.; Xie, Y. Q.; Yuan, D.; Lei, M.; He, P.; Wang, L. J. Org. Chem. 2020, 85, 11014. doi: 10.1021/acs.joc.0c01454
[14]	(a) Xie, Y. B. M. S. Thesis, China Three Gorges University, Yichang, 2017. (in Chinese)
	(谢益碧, 硕士论文, 三峡大学, 宜昌, 2017.)
	(b) Wang, L.; Ren, Z. L.; Ding, M.-W. J. Org. Chem. 2015, 80, 641. doi: 10.1021/jo502275f

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[14]	蒋增强, 张杰, 童耀, 史雪松, 苗大状, 韩世清. 铜催化一锅法合成吡咯[1,2-a]喹喔啉衍生物[J]. 有机化学, 2014, 34(9): 1845-1850.
[15]	王立举, 阿布拉江·克依木, 古丽斯坦·阿布里来提, 卡马勒别克·吾买尔, 糟新民. Cs₂CO₃催化三组分“一锅法”合成5-氨基-7-芳基-7,8-二氢-[1,2,4]三唑并[4,3-a]嘧啶-6-腈衍生物[J]. 有机化学, 2013, 33(10): 2205-2209.