Chlorination of Arylaldehyde-Derived Arylsulfonylhydrazones with N-Chlorosuccinimide Leading to 1,2,4,5-Tetrazine Derivatives

Yuan-Zhao Ji; Hui-Jing Li; Ying Liu; Yan-Chao Wu

doi:10.1055/s-0039-1690712

Synthesis, Table of Contents

Synthesis 2020; 52(01): 69-74
DOI: 10.1055/s-0039-1690712

paper

Chlorination of Arylaldehyde-Derived Arylsulfonylhydrazones with N-Chlorosuccinimide Leading to 1,2,4,5-Tetrazine Derivatives

Yuan-Zhao Ji

^aSchool of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China

,

Hui-Jing Li∗

^aSchool of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China

^bWeihai Institute of Marine Biomedical Industrial Technology, Wendeng District, Weihai 264400, P. R. of China Email: lihuijing@iccas.ac.cn Email: ycwu@iccas.ac.cn

,

Ying Liu

^aSchool of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China

^bWeihai Institute of Marine Biomedical Industrial Technology, Wendeng District, Weihai 264400, P. R. of China Email: lihuijing@iccas.ac.cn Email: ycwu@iccas.ac.cn

,

Yan-Chao Wu ∗

^aSchool of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China

^bWeihai Institute of Marine Biomedical Industrial Technology, Wendeng District, Weihai 264400, P. R. of China Email: lihuijing@iccas.ac.cn Email: ycwu@iccas.ac.cn

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Abstract

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Abstract

It has been reported previously that treatment of arylketone-derived arylsulfonylhydrazones with NXS/(nBu)₄NX affords exclusively vinyl halides. In contrast, we have found that treatment of arylaldehyde-derived arylsulfonylhydrazones with N-chlorosuccinimide in the presence of potassium hydroxide affords 1,2,4,5-tetrazine derivatives in good to excellent yields. The present reactions are carried out under metal-free and mild reaction conditions.

Key words

1,2,4,5-tetrazines - hydrazones - N-chlorosuccinimide - chlorination - metal-free

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References

References

1a Mayer S, Lang K. Synthesis 2017; 49: 830
1b Šečkutė J, Devaraj NK. Curr. Opin. Chem. Biol. 2013; 17: 761
1c Knall AC, Slugovc C. Chem. Soc. Rev. 2013; 42: 5131
1d Devaraj NK, Weissleder R. Acc. Chem. Res. 2011; 44: 816
1e Clavier G, Audebert P. Chem. Rev. 2010; 110: 3299
1f Saracoglu N. Tetrahedron 2007; 63: 4199
1g Churakov AM, Tartakovsky VA. Chem. Rev. 2004; 104: 2601
1h Kaim W. Coord. Chem. Rev. 2002; 230: 127

2a Hwang DK, Dasari RR, Fenoll M, Alain-Rizzo V, Dindar A, Shim JW, Deb N, Fuentes-Hernandez C, Barlow S, Bucknall DG, Audebert P, Marder SR, Kippelen B. Adv. Mater. 2012; 24: 4445
2b Li Z, Ding J, Song N, Du X, Zhou J, Lu J, Tao Y. Chem. Mater. 2011; 23: 1977
2c Li Z, Ding J, Song N, Lu J, Tao Y. J. Am. Chem. Soc. 2010; 132: 13160

3a Tang J, Chen D, Zhang G, Yang H, Cheng G. Synlett 2019; 30: 885
3b Chen D, Yang H, Yi Z, Xiong H, Zhang L, Zhu S, Cheng G. Angew. Chem. Int. Ed. 2018; 57: 2081
3c Chavez DE, Parrish DA, Mitchell L, Imler GH. Angew. Chem. Int. Ed. 2017; 56: 3575
3d Chavez DE, Parrish DA, Mitchell L. Angew. Chem. Int. Ed. 2016; 55: 8666
3e Zhang Q, He C, Yin P, Shreeve JM. Chem. Asian J. 2014; 9: 212
3f Wei H, Gao H, Shreeve JM. Chem. Eur. J. 2014; 20: 16943
3g Gao H, Shreeve JM. Chem. Rev. 2011; 111: 7377

4a Tempas CD, Morris TW, Wisman DL, Le D, Din NU, Williams CG, Wang M, Polezhaev AV, Rahman TS, Caulton KG, Tait SL. Chem. Sci. 2018; 9: 1674
4b Dolinar BS, Alexandropoulos DI, Vignesh KR, James T, Dunbar KR. J. Am. Chem. Soc. 2018; 140: 908
4c Lemes MA, Brunet G, Pialat A, Ungur L, Korobkova I, Murugesu M. Chem. Commun. 2017; 53: 8660
4d Alexandropoulos DI, Dolinar BS, Vignesh KR, Dunbar KR. J. Am. Chem. Soc. 2017; 139: 11040
4e Woods TJ, Ballesteros-Rivas MF, Ostrovsky SM, Palii AV, Reu OS, Klokishner SI, Dunbar KR. Chem. Eur. J. 2015; 21: 10302

5a Audebert P, Miomandre F. Chem. Sci. 2013; 4: 575
5b Quinton C, Alain-Rizzo V, Dumas-Verdes C, Clavier G, Miomandre F, Audebert P. Eur. J. Org. Chem. 2012; 1394
5c Miomandre F, Meallet-Renault R, Vachon JJ, Pansu RB, Audebert P. Chem. Commun. 2008; 1913
5d Kim Y, Kim E, Clavier G, Audebert P. Chem. Commun. 2006; 3612

6a Karaki F, Ohgane K, Imai H, Itoh K, Fujii H. Eur. J. Org. Chem. 2017; 3815
6b Adib M, Soheilizad M, Zhu LG, Wu J. Synlett 2015; 26: 177
6c Lang K, Davis L, Wallace S, Mahesh M, Cox DJ, Blackman ML, Fox JM, Chin JW. J. Am. Chem. Soc. 2012; 134: 10317
6d Zeng Z, Hyer WS, Twamley B, Shreeve JM. Synthesis 2008; 1775
6e Müller J, Troschütz R. Synthesis 2006; 1513
6f Hamasaki A, Zimpleman JM, Hwang I, Boger DL. J. Am. Chem. Soc. 2005; 127: 10767
6g Boger DL, Hong J. J. Am. Chem. Soc. 2001; 123: 8515

7a Proverbio M, Procopio EQ, Panigati M, Mercurio S, Pennati R, Ascagni M, Leone R, Porta CL, Sugni M. Org. Biomol. Chem. 2019; 17: 509
7b Wu H, Devaraj NK. Acc. Chem. Res. 2018; 51: 1249
7c Oliveira BL, Bernardes GJ. L. Chem. Soc. Rev. 2017; 46: 4895
7d Wu H, Devaraj NK. Top. Curr. Chem. 2016; 374: 3
7e Oliveira BL, Guo Z, Boutureira O, Guerreiro A, Jiménez-Osés G, Bernardes GJ. L. Angew. Chem. Int. Ed. 2016; 55: 14683
7f Maggi A, Ruivo E, Fissers J, Vangestel C, Chatterjee S, Joossens J, Sobott F, Staelens S, Stroobants S, Van Der Veken P, Wyffels L, Augustyns K. Org. Biomol. Chem. 2016; 14: 7544
7g Wieczorek A, Werther P, Euchner J, Wombacher R. Chem. Sci. 2017; 8: 1506
7h Wu H, Yang J, Šečkutė J, Devaraj NK. Angew. Chem. Int. Ed. 2014; 53: 5805
7i Devaraj NK, Weissleder R, Hilderbrand SA. Bioconjugate Chem. 2008; 19: 2297

8a Mao W, Shi W, Li J, Su D, Wang X, Zhang L, Pan L, Wu X, Wu H. Angew. Chem. Int. Ed. 2019; 58: 1106
8b Li C, Ge H, Yin B, She M, Liu P, Lia X, Li J. RSC Adv. 2015; 5: 12277
8c Yang J, Karver MR, Li W, Sahu S, Devaraj NK. Angew. Chem. Int. Ed. 2012; 51: 5222
8d Bowie RA, Gardner MD, Neilson DG, Watson KM, Mahmood S, Ridd V. J. Chem. Soc., Perkin Trans. 1 1972; 2395

9a Qu Y, Sauvage FX, Clavier G, Miomandre F, Audebert P. Angew. Chem. Int. Ed. 2018; 57: 12057
9b Fang Z, Hu WL, Liu DY, Yua CY, Hu XG. Green Chem. 2017; 19: 1299
9c Lv LP, Zhou XF, Shi HB, Gao JR, Hu WX. J. Chem. Res. 2014; 38: 368
9d Liu H, Wei Y. Tetrahedron Lett. 2013; 54: 4645
9e Pican S, Lapinte V, Pilard JF, Pasquinet E, Beller L, Fontaine L, Poullain D. Synlett 2009; 731
9f Hu WX, Lv LP, Xu F, Shi HB. J. Chem. Res. 2006; 324
9g Benassuti LD, Garanti L, Molteni G. Tetrahedron 2004; 60: 4627

10a Arunprasath D, Bala BD, Sekar G. Adv. Synth. Catal. 2019; 361: 1172
10b Wang H, Deng YH, Shao Z. Synthesis 2018; 50: 2281
10c Qiu D, Mo F, Zhang Y, Wang J. Adv. Organomet. Chem. 2017; 67: 151
10d Jadhav AP, Ray D, Rao VU. B, Singh RP. Eur. J. Org. Chem. 2016; 2369
10e Mao S, Gao YR, Zhu XQ, Guo DD, Wang YQ. Org. Lett. 2015; 17: 1692
10f Xu K, Shen C, Shan S. Chin. J. Org. Chem. 2015; 35: 294
10g Xiao Q, Zhang Y, Wang J. Acc. Chem. Res. 2013; 46: 236
10h Zhang Y, Wang J. Top. Curr. Chem. 2012; 327: 239
10i Shao Z, Zhang H. Chem. Soc. Rev. 2012; 41: 560
10j Barluenga J, Valdés C. Angew. Chem. Int. Ed. 2011; 50: 7486

11a Wang JL, Li HJ, Wu YC. J. Org. Chem. 2018; 83: 8716
11b Wang HS, Li HJ, Zhang ZG, Wu YC. Eur. J. Org. Chem. 2018; 915
11c Wang H.-S, Li H.-J, Nan X, Luo Y.-Y, Wu Y.-C. J. Org. Chem. 2017; 82: 12914
11d Wu QX, Li HJ, Wang HS, Zhang ZG, Wang CC, Wu YC. Synlett 2015; 26: 243

12a Xia Y, Wang J. Chem. Soc. Rev. 2017; 46: 2306
12b Chen Z, Liu Z, Cao G, Li H, Ren H. Adv. Synth. Catal. 2017; 359: 202
12c Sha Q, Liu H, Wei Y. Eur. J. Org. Chem. 2014; 7707

13 Ojha DP, Prabhu KR. Org. Lett. 2015; 17: 18
14 CCDC 1939331 (2c) and CCDC 1939330 (2e) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

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