Electrophilic Halogen Reagents-mediated Halogenation: Synthesis of Halogenated Dihydro-1,3-oxazine Derivatives

doi:10.1007/s40242-022-2289-1

Abstract

Abstract: Halogenation of N-cinnamylbenzamides and N-[(2H- chromen-3-yl)methyl]benzamides using electrophilic halogen source was reported. Various halogenated dihydro- 1,3-oxazine derivatives (45 examples) were synthesized in high to excellent yields (up to 98% yields), as well as halogenated dihydrochromeno-1,3-oxazine derivatives (56 examples, up to 96% yields). The properties of mild conditions, metal-free and high efficiency of the reaction made it a promising strategy in future applications for the construction of carbon-halogen (fluorine, F; chlorine, Cl; bromine, Br; iodine, I) bond and 1,3-oxazine derivatives.

Key words: Carbon halogen bond, 1,3-Oxazine, Heterocyclization

QI Liang, QIN Yuji, WANG Xueqing, CHAI Hongli, ZHU Weiwei, and ZHOU Yifeng. Electrophilic Halogen Reagents-mediated Halogenation: Synthesis of Halogenated Dihydro-1,3-oxazine Derivatives[J]. Chemical Research in Chinese Universities, 2023, 39(6): 933-947.

References

[1] Mbaba M., Dingle L. M. K., Zulu A. I., Laming D., Swart T., Mare J. A., Hoppe H. C., Edkins A. L., Khanye S. D., Molecules, 2021, 26, 1333
[2] Asif M., Imran M., Int. J. New. Chem., 2020, 7, 60
[3] Zinad D. S., Chem. Biol. Drug Des., 2019, 1, 32
[4] Asifa M., Imranb M., Int. J. New. Chem., 2020, 7, 60
[5] Tasneem R. M., J. Heterocycl. Chem., 2020, 57, 1111
[6] Arikkatt M. C. S., Girly V. K. K., Bhat A. R., Rev., 2013, 4, 134
[7] Sindhu T. J., Arikkatt S. D., Vincent G., Chandran M., Bhat A. R. Krishnakumar K., Int. J. Pharm. Sci. Res., 2013, 4, 134
[8] Dhafer S. Z., Ahmed M., Ranjan K. M., Ashish K. S., Mohammad R. F. P., Chem. Biol. Drug Des., 2020, 95, 16
[9] Betokali K. Z., Putusenla I., Tovishe P., Tetrahedron, 2022, 109, 1322
[10] Kenji N., Kouki F., J. Med. Chem., 2018, 13, 5525
[11] Kouki F., Yasunori M., J. Med. Chem., 2018, 12, 5122
[12] Rabia Q., Aamer S., Maria S., Zaman A., Qamar A., Mubashir H., Fernando A., Drug Dev. Des., 2018, 79, 352
[13] George M., Joseph L., Sadanandan H. R., Rev., 2016, 6, 1
[14] Dou G. L., Sun F., Zhao X., Shi D. Q., Chin. J. Chem., 2011, 29, 2465
[15] Kouki F., Moriyasu M., Shuhei Y., Kenichi K., Tetrahedron, 2021, 64, 152684
[16] Alexey Y. S., Sema L. L., Chem. Rev., 2011, 111, 5004
[17] Yakovlev I. P., Prep'yalov A. V., Ivin B. A., Chem. Heterocycl. Compd., 1994, 30, 255
[18] Chirachanchai S., Laobuthee A., Phongtamburg S., Siripatanasarakit W., Ishida H., J. Appl. Polym. Sci., 2000, 77, 2561
[19] Oh K. S., Lee S., Choi J. K., Lee B. H., Comb. Chem. High Throughput Screen, 2010, 13, 790
[20] Cho S. Y., Baek J. Y., Han S. S., Kang S. K., Ha J. D., Ahn J. H., Lee J. D., Kim K. R., Cheon H. G., Rhee S. D., Yang S. D., Yon G. H., Pak C. S., Choi J. K., Bioorg. Med. Chem. Lett., 2006, 16, 499
[21] Kurlykin M. P., Dudkina M. M., Ten’kovtsev A. V., Polym. Sci. Ser. B, 2019, 61, 51
[22] Wang X. J., Gu C., Zheng H. Z., Zhang Y. M., Chem. Asian J., 2018, 3, 15
[23] Oliveira D. R. D., Mazzetto S. E., Lomonaco D., Int. J. Polym. Sci., 2018, 13
[24] Zivani V., Jungyeon K., Becer C. R., Eur. Polym. J., 2021, 147, 110299
[25] Fang B., Lu X., Hu J., Zhang G., Zheng X., He L., Cao J., Gu J., Cao F., J. Colloid Interface Sci., 2019, 536, 516
[26] Anan Z., Robert L., Adv. Healthcare Mater., 2021, 10, 2001382
[27] Ankit L., Bijoy P., Mathew B. P., Mahendra N., Curr. Org. Chem., 2021, 25, 133
[28] Palchykov V. A., Gaponov A. A., In. Adv. Heterocycl. Chem., 2019, 7, 54
[29] Gaonkar S. L., Nagaraj V. U., Nayak S., Inorg. Chem., 2019, 16, 43
[30] Zhu W. W., Zhen X., Wu J. Y., Cheng Y. P., An J. K., Ma X. Y., Liu J. K., Qin Y. J., Zhu H., Xue J. J., Jiang X. X., Nat. Commun., 2021, 12, 3957
[31] Mehdi G., Abolfazl O., Saeed R., Synth. Commun., 2008, 38, 4125
[32] Ghulam S., Imran S., Ammer S., J. Heterocycl. Chem., 2022, 1, 34
[33] Assy M. G., Hassan A. E. S., Nabil H., Ahmed H., Hesham A. M., J. Heterocycl. Chem., 2019, 8, 29
[34] Einaru S., Shitamichi K., Nagano T., Matsumoto A., Asano K., Matsubara S., Angew. Chem. Int. Ed., 2018, 57, 13863
[35] Wu G. R., Fu X. P., Wang Y. Y., Deng K. Z., Zhang L. L., Ma T., Ji Y. F., Org. Lett., 2020, 22, 7003
[36] Sun J., Gong H., Yan C. G., Chin. J. Chem., 2015, 33, 1049
[37] Betokali K., Putusenla I., Tovishe P., Tetrahedron, 2022, 109, 132672
[38] Blunt J. W., Copp B. R., Keyzers R. A., Munro M. H. G., Prinsep M. R., Nat. Prod. Rep., 2012, 29, 144
[39] Muller K., Faeh C., Diederich F., Sci., 2007, 317, 1881
[40] Hernandes M. Z., Cavalcanti S. M. T., Moreira D. R. M., Azevedo W. F., Leite A. C. L., Curr. Drug Targets, 2010, 11, 303
[41] Jeschke P., Pest Manage. Sci., 2010, 66, 10
[42] Amanchukwu C. V., Harding J. R., Horn Y. S., Hammond P. T., Chem. Mater., 2015, 27, 550
[43] Borissov A., Maurya Y. K., Moshniaha L., Wong W. S., Znkarwowska M., Stepien M., Chem. Rev., 2022, 122, 565
[44] Crowe C., Molyneux S., Sharma S. V., Zhang Y., Gkotsi D. S., Connaris H., Goss R., J. M. Chem. Soc. Rev., 2021, 50, 9443
[45] Rauniyar V., Lackner A. D., Hamilton G. L., Toste F. D., Science, 2011, 334, 1681
[46] Coelho J. A. S., Matsumoto A., Orlandi M., Hilton M. J., Sigman M. S., Toste F. D., Chem. Sci., 2018, 9, 7153
[47] Zhao J. F., Duan X. H., Yang H., Guo L. N., J. Org. Chem., 2015, 80, 11149
[48] Danahy K. E., Cooper J. C., Humbeck J. F. V., Agew. Chem. Int. Ed., 2018, 57, 5134
[49] Wu S. W., Liu F., Org. Lett., 2016, 18, 3642
[50] Benito A., Pedro A., Sara C., Teresa M. C., Alejandro M., Chem. Commun., 2016, 52, 6813
[51] Jiang H., Studer A., Angew. Chem. Int. Ed., 2018, 57, 10707
[52] Li Z. H., Fiser B., Jiang B. L., Li J. W., Xu B. H., Zhang S., J. Org. Biomol. Chem., 2019, 17, 3403
[53] Song S., Li X. Y., Wei J. L., Wang W. J., Zhang Y. Q., Ai L. S., Zhu Y. C., Shi X. M., Zhang X. H., Jiao N., Nat. Catal., 2020, 3, 107
[54] Qu Z. W., Zhu H., Grimme S., CheCatChem., 2020, 13, 207
[55] Li Z. H., Fiser B., Jiang B. L., Li J. W., Xu B. H., Zhang S., J. Org. Biomol. Chem., 2019, 17, 3403
[56] Nishimura K., Wang Y. Z., Ogura Y., Kumagai J., Ishihara K., ACS Catal., 2022, 12, 1012
[57] Lizano E., Grima J., Pujol M. D., Synlett., 2019, 30, 2000
[58] Liu Y., Leng H. J., Li Q. Z., Li J. L., Adv. Syn., 2020, 362, 3926
[59] Khanal H. D., Thombal R. S., Maezono S. M. B., Lee Y. R., Adv. Syn., 2018, 360, 3185
[60] Jiang X. J., Xu X., Xu W., Yu P., Yang Y. Y., Org. Lett., 2021, 23, 6316
[61] Varenikov A., Shapiro E., Gandelman M., Chem. Rev., 2021, 121, 412
[62] Zebrowski P., Eder I., Eitzinger A., Mallojjala S. C., Waser M., ACS Org. Inorg. Au., 2022, 2, 34
[63] He H. Q., Liu Z., Wang W., Jiang X. J., Bioorg. Med. Chem., 2020, 38, 115281
[64] Li J., Kwon E., Lear M. J., Hayashi Y., Helv C., Acta, 2021, 104, 2100080
[65] Li S., Li Z. K., Yuan Y. F., Li Y. J., Zhang L. S., Wu Y. M., Chem. Eur. J., 2013, 19, 1496
[66] Ma C. Q., Xing D., Hu W. H., Org. Lett., 2016, 18, 3134
[67] Doyley J. M., Aliev A. E., Sheppard T. D., Angew. Chem. Int. Ed., 2014, 53, 10747
[68] Kuang G. H., Liu D. D., Chen X. R., Liu G. Y., Fu Y., Peng Y. Y., Li H., Zhou Y. R., Org. Lett., 2021, 23, 8402
[69] Mulahmetovic E., Hargaden G. C., Mini-Rev. Org. Chem., 2019, 16, 507
[70] Kosjek T., Heath E., Iskra J., Halogen Heterocycl., 2011, 27, 219
[71] Zhu Y., Han J. L., Wang J. D., Norio S., Mikiko S., Vadim S. A., Jaime A. S. C., Toste F. D., Chem. Rev., 2018, 118, 3887
[72] Furuya T., Kamlet A. S., Ritter T., Nature, 2011, 473, 470
[73] Hiyama T., Yamamoto H., Organofluorine Compounds., 2000, 137
[74] Szpera R., Moseley D. F. J., Smith L. B., Sterling A. J., Gouverneur V., Angew. Chem. Int. Ed., 2019, 58, 14824
[75] Cao T. T., Zhang W. K., Qin F. H., Kang Q. Q., Dong Y. R., Li Q., Kang C., Wei W. T., ACS Sustain. Chem. Eng., 2020, 8, 16946
[76] Egami H., Niwa T., Sato H., Hotta R., Rouno D., Kawato Y., Hamashima Y., J. Am. Chem. Soc., 2018, 140, 2785
[77] Okuma K., Yasuda T., Shioji K., Yokomori Y., Bull. Chem. Soc. Jpn., 2007, 80, 1824