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Synlett 2023; 34(08): 963-969
DOI: 10.1055/a-1969-4050
DOI: 10.1055/a-1969-4050
letter
Synthesis of 1,3-Diaryltriazenes and Azo Dyes from Aryl Amines Using N-Nitrososulfonamides
This material is based upon work supported by the National Science Foundation (Grant No. 1752821, R.D.B).
Abstract
New methods for the synthesis of 1,3-diaryltriazenes and azo dyes from aryl amines are reported. Both methods involve the formation of aryl diazonium intermediates via the transnitrosation of aryl amines with N-nitrososulfonamides. Each two-step transformation may be performed in one reaction vessel at room temperature with no precautions taken to exclude air or moisture. Several triazene and azo dye structures are reported here for the first time, demonstrating the utility of operating the two-step reaction sequence under mild conditions.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1969-4050.
- Supporting Information
Publication History
Received: 27 September 2022
Accepted after revision: 27 October 2022
Accepted Manuscript online:
27 October 2022
Article published online:
05 January 2023
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References
- 1 Zhang F, Chen Z, Cheung CW, Ma J. Chin. J. Chem. 2020; 38: 1132
- 2 Griess JP. Justus Liebigs Ann. Chem. 1858; 106: 123
- 3 Mo F, Dong G, Zhang Y, Wang J. Org. Biomol. Chem. 2013; 11: 1582
- 4 Merino E. Chem. Soc. Rev. 2011; 40: 3835
- 5 Mahouche-Chergui S, Gam-Derouich S, Mangeney C, Chehimi MM. Chem. Soc. Rev. 2011; 40: 4143
- 6 Cao C, Zhang Y, Jiang C, Qi M, Liu G. ACS Appl. Mater. Interfaces 2017; 9: 5031
- 7a Szele I, Zollinger H. Top. Curr. Chem. 1983; 112: 1
- 7b Sandmeyer Reaction . In Comprehensive Organic Name Reactions and Reagents . Wang Z. John Wiley & Sons; Hoboken, NJ: 2010: 2471-2475
- 8 Kimball DB, Haley MM. Angew. Chem. Int. Ed. 2002; 41: 3338
- 9 Suleymanov AA, Severin K. Angew. Chem. Int. Ed. 2021; 60: 6879
- 10 Nicolaou KC, Boddy CN. C, Li H, Koumbis AE, Hughes R, Natarajan S, Jain NF, Ramanjulu JM, Bräse S, Solomon ME. Chem. Eur. J. 1999; 5: 2602
- 11 Jones L, Schumm JS, Tour JM. J. Org. Chem. 1997; 62: 1388
- 12 Wirschun W, Winkler M, Lutz K, Jochims JC. J. Chem. Soc., Perkin Trans. 1998; 1755
- 13 Cappoen D, Vajs J, Uythethofken C, Virag A, Mathys V, Kočevar M, Verschaeve L, Gazvoda M, Polanc S, Huygen K, Košmrlj J. Eur. J. Med. Chem. 2014; 77: 193
- 14 Hill DT, Stanley KG, Williams JE. K, Loev B, Fowler PJ, McCafferty JP, Macko E, Berkoff CE, Ladd CB. J. Med. Chem. 1983; 26: 865
- 15 dos SantosA. J. R. W. A, Bersch P, de Oliveira HP. M, Hörner M, Paraginski GL. J. Mol. Struct. 2014; 1060: 264
- 16 Sharma P, Dayma V, Dwivedi A, Baroliya PK, Tripathi IP, Vanangamudi M, Chauhan RS, Goswami AK. Bioorg. Chem. 2020; 96: 103642
- 17 Kuriakose S, Uzonna JE. Int. Immunopharmacol. 2014; 21: 342
- 18 Marchesi F, Turriziani M, Tortorelli G, Avvisati G, Torino F, Devecchis L. Pharmacol. Res. 2007; 56: 275
- 19 Figueirêdo P. deM. S, Sampaio Filho JC, Sodré A. deJ. S, de Castro Júnior JR, Gonçalves IS, Blasques RV, Correa RS, Lima BA. V, dos Anjos Marques L, Coutinho DF, de Azevedodos Santos AP. S, Luz TR. S. A, de Miranda R. deC. M, dos Santos JR. A, Doriguetto AC, Pividori MI, Hörner M, Villis PC. M. Sci. Rep. 2021; 11: 2541
- 20 Işık M, Akocak S, Lolak N, Taslimi P, Türkeş C, Gülçin İ, Durgun M, Beydemir Ş. Arch. Pharm. (Weinheim, Ger.) 2020; 353: 2000102
- 21 Xue D, Luo S.-P, Zhan S.-Z. Appl. Organometal. Chem. 2018; 32: e3997
- 22 Industrial Dyes: Chemistry, Properties, Applications. Hunger K. Wiley-VCH; Weinheim: 2003
- 23 Benkhaya S, Harfi SE, Harfi AE. Appl. J. Environ. Eng. Sci. 2017; 3: 311
- 24a Ali Y, Hamid SA, Rashid U. Mini-Rev. Med. Chem. 2018; 18: 1548
- 24b Zhao X, Ha W, Gao K, Shi Y. Anal. Chem. 2020; 92: 9039
- 25 Tahir T, Ashfaq M, Saleem M, Rafiq M, Shahzad MI, Kotwica-Mojzych K, Mojzych M. Molecules 2021; 26: 4872
- 26 Raveendra RS, Prashanth PA, Hari Krishna R, Bhagya NP, Nagabhushana BM, Raja Naika H, Lingaraju K, Nagabhushana H, Daruka Prasad B. J. Asian Ceram. Soc. 2014; 2: 357
- 27 Lv M, Ma J, Li Q, Xu H. Bioorg. Med. Chem. Lett. 2018; 28: 181
- 28 Ashfaq TT. M, Shahzad MI, Tabassum R. Thai J. Vet. Med. 2020; 50: 435
- 29 Unnisa A, Abouzied AS, Baratman A, Chenchu Lakshmi KN. V, Hussain T, Kunduru RD, Banu H, Bushra Fatima S, Hussian A, Selvarajan KK. Arab. J. Chem. 2020; 13: 8638
- 30 Khedr AM, El-Ghamry H, Kassem MA, Saad FA, El-Guesmi N. Inorg. Chem. Commun. 2019; 108: 107496
- 31a Galloway JD, Sarabia C, Fettinger JC, Hratchian HP, Baxter RD. Org. Lett. 2021; 23: 3253
- 31b Yaghoubi M, Rajaram P, Sarabia C, Baxter R. 3,3-Dimethyl-2-Nitroso-2,3-Dihydrobenzo[d]Isothiazole-1,1-Dioxide. In Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons; Hoboken, NJ: 2022.
- 32 Budavari S. Vogel’s Textbook of Practical Organic Chemistry, 5th ed. Furniss BS, Hannaford AJ, Smith PW. G, Tatchell AR. Longman Scientific & Technical; Essex: 1989
- 33 Vernin G, Siv C, Metzger J, Párkányi C. Synthesis 1977; 691
- 34 Ogata Y, Nakagawa Y, Inaishi M. Bull. Chem. Soc. Jpn. 1981; 54: 2853
- 35 Deev SL, Khalymbadzha IA, Shestakova TS, Charushin VN, Chupakhin ON. RSC Adv. 2019; 9: 26856
- 36 Kumar RK, Ali MA, Punniyamurthy T. Org. Lett. 2011; 13: 2102