金催化2-炔基芳基叠氮氧化重排一锅法快速合成苯并噁嗪-4-酮

doi:10.6023/cjoc201706030

有机化学 ›› 2018, Vol. 38 ›› Issue (1): 208-214.DOI: 10.6023/cjoc201706030 上一篇下一篇

所属专题：庆祝吴养洁院士九十华诞专辑

研究论文

金催化2-炔基芳基叠氮氧化重排一锅法快速合成苯并噁嗪-4-酮

张小祥, 吕昌, 李萍, 雍万雄, 李静, 朱新宝

南京林业大学化工学院江苏省生物质绿色燃料与化学品重点实验室南京 210037

收稿日期:2017-06-23 修回日期:2017-08-17 发布日期:2017-09-15
通讯作者: 张小祥, 朱新宝 E-mail:zhangxiaoxiang@njfu.edu.cn;zhuxinbao@njfu.com.cn
基金资助:
Project supported by the Project supported by the Young National Natural Science Foundation of China (No. 21302096), the Young Natural Science Foundation of Jiangsu Province (Nos. BK20171449, BK20130962), the Postgraduate Research & Practice Innovation Program of Jiangsu Province (No. KYLX16_0844), and the Project Fund from the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).

Rapid Access to 4H-3, 1-Benzoxazin-4-ones via Gold-Catalyzed One-Pot Oxidative Rearrangement of 2-Alkynyl Arylazides

Zhang Xiaoxiang, Lü Chang, Li Ping, Yong Wanxiong, Li Jing, Zhu Xinbao

Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037

Received:2017-06-23 Revised:2017-08-17 Published:2017-09-15
Contact: 10.6023/cjoc201706030 E-mail:zhangxiaoxiang@njfu.edu.cn;zhuxinbao@njfu.com.cn
Supported by:
Project supported by the Project supported by the Young National Natural Science Foundation of China (No. 21302096), the Young Natural Science Foundation of Jiangsu Province (Nos. BK20171449, BK20130962), the Postgraduate Research & Practice Innovation Program of Jiangsu Province (No. KYLX16_0844), and the Project Fund from the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).

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1. 金催化2-炔基芳基叠氮氧化重排一锅法快速合成苯并噁嗪-4-酮.PDF(525KB)

摘要/Abstract

通过金催化2-炔基芳基叠氮的氧化重排，发展了一种一锅一步法快速有效合成4H-3，1-苯并噁嗪-4-酮衍生物的方法.在不苛刻的条件下，目标产物可以达到中等到非常好的产率.该反应的特点在于以醋酸作溶剂的条件下，大多数反应进行的比较快，通常在1 h以内.

关键词: 金催化, 氧化重排, 一锅法, 2-炔基芳基叠氮

The one-pot one-step synthetic method of 4H-3,1-benzoxazin-4-ones via the gold-catalyzed oxidative rearrangement of 2-alkynyl arylazides has been developed. The desired products were obtained in moderate to excellent yields under mild reaction conditions. In most cases, using acetic acid as solvent the reactions were shown to proceed very fast within 1 h.

Key words: gold-catalyzed, oxidative rearrangement, one-pot, 2-alkynyl arylazides

引用此文

张小祥, 吕昌, 李萍, 雍万雄, 李静, 朱新宝. 金催化2-炔基芳基叠氮氧化重排一锅法快速合成苯并噁嗪-4-酮[J]. 有机化学, 2018, 38(1): 208-214.

Zhang Xiaoxiang, Lü Chang, Li Ping, Yong Wanxiong, Li Jing, Zhu Xinbao. Rapid Access to 4H-3, 1-Benzoxazin-4-ones via Gold-Catalyzed One-Pot Oxidative Rearrangement of 2-Alkynyl Arylazides[J]. Chin. J. Org. Chem., 2018, 38(1): 208-214.

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参考文献

[1] (a) Padwal, R. Curr. Opin. Invest. Drugs 2008, 9, 414.
(b) Eissa, A. M. F.; El-Sayed, R. J. Heterocycl. Chem. 2006, 43, 1.
(c) Neumann, U.; Schechter, N. M.; Gutschow, M. Bioorg. Med. Chem. 2001, 9, 947.
(d) Gutschow, M.; Neumann, U. Bioorg. Med. Chem. 1997, 5, 1935.
(e) Krantz, A.; Spencer, R. W.; Tam, T. F.; Liak, T. J.; Copp, L. J.; Thomas, E. M.; Rafferty, S. P. J. Med. Chem. 1990, 33, 464.
[2] (a) Krantz, A.; Spencer, R. W.; Tam, T. F.; Liak, T. J.; Copp, L. J.; Thomas, E. M.; Rafferty, S. P. J. Med. Chem. 1990, 33, 464.
(b) Stein, R. L.; Strimpler, A. M.; Viscarello, B. R.; Wildonger, R. A.; Mauger, R. C.; Trainor, D. A. Biochemistry 1987, 26, 4126.
[3] For some examples, see:(a) Yamada, Y.; Kato, T.; Ogino, H.; Ashina, S.; Kato, K. Horm. Metab. Res. 2008, 40, 539.
(b) Padwal, R. Curr. Opin. Invest. Drugs 2008, 9, 414.
[4] Hedstrom, L.; Moorman, A. R.; Dobbs, J.; Abeles, R. H. Biochemistry 1984, 23, 1753.
[5] Jarvest, R. L.; Parratt, M. J.; Debouck, C. M.; Gorniak, J. G.; Jennings, L. J.; Serafinowska, H. T.; Strickler, J. E. Bioorg. Med. Chem. Lett. 1996, 6, 2463.
[6] (a) Li, W. F.; Wu, X. F. J. Org. Chem. 2014, 79, 10410.
(b) Yamashita, M.; Iida, A. Tetrahedron Lett. 2014, 55, 2991.
(c) Lian, X. L.; Lei, H.; Quan, X. J.; Ren, Z. H.; Wang, Y. Y.;. Guan, Z. H. Chem. Commun. 2013, 49, 8196.
(d) Ge, Z. Y.; Xu, Q. M.; Fei, X. D.; Tang, T.; Zhu, Y. M.; Ji, S. J. J. Org. Chem. 2013, 78, 4524.
(e) Xie, Y. Y.; Wang, S. P. J. Chem. Res. 2012, 36, 123.
(f) Wu X. F.; Neumann, H.; Beller, M. Chem. Eur. J. 2012, 18, 12599.
(g) Kumar, R. A.; Maheswari, C. U.; Ghantasala, S.; Jyothi, C.; Reddy, K. R. Adv. Synth. Catal. 2011, 353, 401.
(h) Xue, S.; McKenna, J.; Shieh, W. C.; Repic, O. J. Org. Chem. 2004, 69, 6474.
(i) Chenard, B. L.; Welch, W. M.; Blake, J. F.; Butler, T. W.; Reinhold, A.; Ewing, F. E.; Menniti, F. S.; Pagnozzi, M. J. J. Med. Chem. 2001, 44, 1710.
(j) Coppola, G. M. J. Heterocycl. Chem. 1999, 36, 563.
(k) Larksarp, C.; Alper, H. Org. Lett. 1999, 1, 1619.
(l) Kotsuki, H.; Sakai, H.; Morimoto, H.; Suenaga, H. Synlett 1999, 1993.
(m) Cacchi, S.; Fabrizi, G.; Marinelli, F. Synlett 1996, 997.
(n) Larock, R. C;. Fellows, C. A. J. Org. Chem. 1980, 45, 363.
(o) Errede, L. A. J. Org. Chem. 1976, 41, 1763.
(p) Jackson, T. G.; Morris, S. R.; Turner, R. H. J. Chem. Soc. 1968, 13, 1592.
(q) Taylor, E. C.; Knopf, R. I.; Borror, A. L. J. Am. Chem. Soc. 1960, 82, 3152.
[7] For recent examples on the synthesis of 4H-3,1-benzoxazin-4-ones 3, see:(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.
(b) Verma, A.; Kumar, S. Org. Lett. 2016, 18, 4388.
(c) Arcadi, A.; Chiarini, M.; Vecchio, L. D.; Marinelli, F.; Michelet, V. Chem. Commun. 2016, 52, 1458.
(d) Laha, J. K.; Patel, K. V.; Tummalapalli, K. S. S.; Dayal, N. Chem. Commun. 2016, 52, 10245.
(e) Prakash, R.; Gogoi, S. Adv. Synth. Catal. 2016, 19, 3046.
(f) Yu, J.; Zhang-Negrerie, D.; Du, Y. Eur. J. Org. Chem. 2016, 2016, 562.
(g) Wu, X. F.; Schranck, J.; Neumann, H.; Beller, M. Chem.-Eur. J. 2011, 17, 12246.
(h) Liu, Q.; Chen, P.; Liu, G. ACS Catal. 2013, 3, 178.
(i) Li, W.; Wu, X. F. J. Org. Chem. 2014, 79, 10410.
(j) Chavan, S. P.; Bhanage, B. M. Eur. J. Org. Chem. 2015, 2015, 2405.
(k) Munusamy, S.; Venkatesan, S.; Sathiyanarayanan, K. I. Tetrahedron Lett. 2015, 56, 203.
(l) Larksarp, C.; Alper, H. Org. Lett. 1999, 1, 1619.
(m) Salvadori, J.; Balducci, E.; Zaza, S.; Petricci, E.; Taddei, M. J. Org. Chem. 2010, 75, 1841.
(n) Nayak, M. K.; Kim, B. H.; Kwon, J. E.; Park, S.; Seo, J.; Chung, J. W.; Park, S. Y. Chem.-Eur. J. 2010, 16, 7437.
[8] For recent selected reviews on gold-catalyzed reactions, see:(a) Harris, R. J.; Widenhoefer, R. A. Chem. Soc. Rev. 2016, 45, 4533.
(b) Asiri, A. M.; Hashmi, A. S. K. Chem. Soc. Rev. 2016, 45, 4471.
(c) Zheng, Z.; Wang, Z.; Wang, Y.; Zhang, L. Chem. Soc. Rev. 2016, 45, 4448.
(d) Ziand, W.; Toste, F. D. Chem. Soc. Rev. 2016, 45, 4567.
(e) Huple, D. B.; Ghorpade, S.; Liu, R.-S. Adv. Synth. Catal. 2016, 358, 1348.
(f) Dorel, R.; Echavarren, A. M. Chem. Rev. 2015, 115, 9028.
(g) Jia, M.; Bandini, M. ACS Catal. 2015, 5, 1638.
(h) Wang, Y.; Muratore, M. E.; Echavarren, A. M. Chem. Eur. J. 2015, 21, 7332.
(i) Zhang, L. Acc. Chem. Res. 2014, 47, 877.
(j) Yeom, H.-S.; Shin, S. Acc. Chem. Res. 2014, 47, 966.
(k) Fensterbank, L.; Malacria, M. Acc. Chem. Res. 2014, 47, 953.
(l) Benitez, D.; Shapiro, N. D.; Tkatchouk, E.; Wang, Y.; God-dard Ⅲ, W. A.; Toste, F. D. Nat. Chem. 2009, 1, 482.
(m) Hashmi, A. S. K. Chem. Rev. 2007, 107, 3180.
(n) Wu, W.-T.; Zhang, L.; You, S.-L. Acta Chim. Sinica 2017, 75, 419(in Chinese).(吴文挺, 张立明, 化学学报, 2017, 75, 419.)
for recent selected examples, see:(o) Zhao, J.-R.; Yuan, X.; Wang, Z.; Chen, S.; Zhang, Z.-X.; Xue, W. Org. Chem. Front. 2015, 2, 34.
(p) Li, L.; Zhou, B.; Ye, L. Chin. J. Org. Chem. 2015, 35, 655(in Chinese).(李龙, 周波, 叶龙武, 有机化学, 2015, 35, 655.)
(q) Zhang, P.-C.; Wang, Y.; Qian, D.; Li, W.; Zhang, J. Chin. J. Chem. 2017, 35, 849.
[9] For recent selected a review on the generation of α-imino gold carbenes, see:Davies, P. W.; Garzûn, M. Asian J. Org. Chem. 2015, 4, 694.
[10] For recent selected examples, see:(a) Lonca, G. H.; Tejo, C.; Chan, H. L.; Chiba, S.; Gagosz, F. Chem. Commun. 2017, 53, 736.
(b) Jin, H.; Tian, B.; Song, X.; Xie, J.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2016, 55, 12688.
(c) Pan, Y.; Chen, G.-W.; Shen, C.-H.; He, W.; Ye, L.-W. Org. Chem. Front. 2016, 3, 391.
(d) Li, N.; Lian, X.-L.; Li, Y.-H.; Wang, T.-Y.; Han, Z.-Y.; Zhang, L.; Gong, L.-Z. Org. Lett. 2016, 18, 4178.
(e) Jin, H.; Huang, L.; Xie, J.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2016, 55, 794.
(f) Zhou, A.-H.; He, Q.; Shu, C.; Yu, Y.-F.; Liu, S.; Zhao, T.; Zhang, W.; Lu, X.; Ye, L.-W. Chem. Sci. 2015, 6, 1265.
(g) Xiao, X.-Y.; Zhou, A.-H.; Shu, C.; Pan, F.; Li, T.; Ye, L-W. Chem.-Asian J. 2015, 10, 1854.
(h) Shen, C.-H.; Pan, Y.; Yu, Y.-F.; Wang, Z.-S.; He, W.; Li, T.; Ye, L.-W. J. Organomet. Chem. 2015, 795, 63.
(i) Li, N.; Wang, T.-Y.; Gong, L.-Z; Zhang, L. Chem.-Eur. J. 2015, 21, 3585.
(j) Shu, C.; Wang, Y.-H.; Zhou, B.; Li, X.-L.; Ping, Y.-F.; Lu, X.; Ye, L.-W. J. Am. Chem. Soc. 2015, 137, 9567.
(k) Zhu, L.; Yu, Y.; Mao, Z.; Huang, X. Org. Lett. 2015, 17, 30.
(l) Wu, Y.; Zhu, L.; Yu, Y.; Luo, X.; Huang, X. J. Org. Chem. 2015, 80, 11407.
(m) Pawar, S. K.; Sahani, R. L.; Liu, R.-S. Chem.-Eur. J. 2015, 21, 10843.
(n) Prechter, A.; Henrion, G.; dit Bel, P. F.; Gagosz, F. Angew. Chem., Int. Ed. 2014, 53, 4959.
(o) Garzón M.; Davies, P. W. Org. Lett. 2014, 16, 4850.
(p) Tokimizu, Y.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2014, 16, 3138.
(q) Chatzopoulou, E.; Davies, P. W. Chem. Commun. 2013, 49, 8617.
(r) Yan, Z.-Y.; Xiao, Y.; Zhang, L. Angew. Chem., Int. Ed. 2012, 51, 8624.
(s) Xiao, Y.; Zhang, L. Org. Lett. 2012, 14, 4662.
(t) Lu, B.; Luo, Y.; Liu, L.; Ye, L.; Wang, Y.; Zhang, L. Angew. Chem., Int. Ed. 2011, 50, 8358.
(u) Wetzel, A.; Gagosz, F. Angew. Chem., Int. Ed. 2011, 50, 7354.
(v) Li, C.; Zhang, L. Org. Lett. 2011, 13, 1738.
(w) Davies, P. W.; Cremones, A.; Dumitrescu, L. Angew. Chem., Int. Ed. 2011, 50, 8931.
(x) Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260.
[11] For our recent studies on gold-catalyzed tandem reactions, see:(a) Chen, C.; Zou, Y.; Chen, X.; Zhang, X.; Rao, W.; Chan, P. W. H. Org. Lett. 2016, 18, 4730.
(b) Zhang, X.; Sun, X.; Fan, H.; Lyu, C.; Li, P.; Zhang, H.; Rao, W. RSC Adv. 2016, 6, 56319.
(c) Zhang, X.; Sun, X.; Fan, H.; Li, P.; Lyu, C.; Rao, W. Eur. J. Org. Chem. 2016, 25, 4265.
(d) Zhang, X.; Sun, X.; Fan, H.; Cui, X.; Ma, M. Chin. J. Org. Chem. 2015, 35, 1469(in Chinese).(张小祥, 孙小萍, 张海飞, 崔杏丽, 马猛涛, 有机化学, 2015, 35, 1469.)
[12] Wang, J.; Jiang, X.; Zhang, Y.; Zhu, Y.; Shen, J. Tetrahedron Lett. 2015, 56, 2349.
[13] Eid, A. I. Eur. J. Med. Chem. 1979, 14, 463.

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金催化2-炔基芳基叠氮氧化重排一锅法快速合成苯并噁嗪-4-酮

Rapid Access to 4H-3, 1-Benzoxazin-4-ones via Gold-Catalyzed One-Pot Oxidative Rearrangement of 2-Alkynyl Arylazides

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