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
收稿日期: 2017-06-23
修回日期: 2017-08-17
网络出版日期: 2017-09-15
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
Received date: 2017-06-23
Revised date: 2017-08-17
Online published: 2017-09-15
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).
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 . DOI: 10.6023/cjoc201706030
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
[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.
/
| 〈 |
|
〉 |
