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Synthesis 2016; 48(08): 1159-1166
DOI: 10.1055/s-0035-1561301
DOI: 10.1055/s-0035-1561301
paper
Aryliminophosphoranes as Key Intermediates in the One-Pot Synthesis of 1-Aryl-1,3-dihydro-2H-benzimidazol-2-ones from N-Aryl-2-nitrosoanilines and Carbon Dioxide under Mild Metal-Free Conditions
Further Information
Publication History
Received: 23 October 2015
Accepted after revision: 27 November 2015
Publication Date:
07 January 2016 (online)
Abstract
A new and convenient protocol is presented for the synthesis of 1-arylbenzimidazol-2-ones by a one-pot reaction of N-aryl-2-nitrosoanilines using solid carbon dioxide as a source of the key carbonyl moiety. The metal-free process is carried out under mild conditions and is compatible with a variety of substituents. The atom economy of the synthesis of the starting nitrosoanilines, accomplished by substitution of hydrogen, makes the entire synthesis of the target compounds environmentally friendly.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561301.
- Supporting Information
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References
- 2 Łukasik E, Wróbel Z. Synthesis 2016; 48: 263
- 3a Wróbel Z, Kwast A. Synlett 2007; 1525
- 3b Wróbel Z, Kwast A. Synthesis 2010; 3865
- 3c Wróbel Z, Stachowska K, Kwast A. Synthesis 2013; 45: 127
- 4 Yu B, He L.-N. ChemSusChem 2015; 8: 52
- 5a Song Q.-W, Yu B, Li X.-D, Ma R, Diao Z.-F, Li R.-G, Li W, He L.-N. Green Chem. 2014; 16: 1633
- 5b Reithofer MR, Sum YN, Zhang Y. Green Chem. 2013; 15: 2086
- 6a Tamura M, Noro K, Honda M, Nakagawa Y, Tomishige K. Green Chem. 2013; 15: 1567
- 6b Tamura M, Noro K, Honda M, Nakagawa Y, Tomishige K. J. Chem. Technol. Biotechnol. 2014; 89: 19
- 7a Zhao Y, Yu B, Yang Z, Zhang H, Hao L, Gao X, Liu Z. Angew. Chem. Int. Ed. 2014; 53: 5922
- 7b Zheng H, Cao X, Du K, Xu J, Zhang P. Green Chem. 2014; 16: 3142
- 7c Xiao Y, Kong X, Xu Z, Cao C, Pang G, Shi Y. RSC Adv. 2015; 5: 5032
- 8 Yu B, Zhang H, Zhao Y, Chen S, Xu J, Huang C, Liu Z. Green Chem. 2013; 15: 95
- 9 Kimura T, Kamata K, Mizuno N. Angew. Chem. Int. Ed. 2012; 51: 6700
- 10 Yu B, Zhang H, Zhao Y, Chen S, Xu J, Hao L, Liu Z. ACS Catal. 2013; 3: 2076
- 11 Wright JB. Chem. Rev. 1951; 48: 397
- 12a Li Z, Sun H, Jiang H, Liu H. Org. Lett. 2008; 10: 3263
- 12b Massarotti A, Brunco A, Sorba G, Tron GC. J. Chem. Inf. Model. 2014; 54: 396
- 12c Benedi C, Bravo F, Uriz P, Fernández E, Claver C, Castillón S. Tetrahedron Lett. 2003; 44: 6073
- 12d Barbero N, Carril M, SanMartin R, Dominguez E. Tetrahedron 2008; 64: 7283
- 13a Chene P, Floersheimer A, Furet P, Shoepfer J. WO 2006010594, 2006
- 13b Bruncko M, Tahir SK, Song X, Chen J, Ding H, Huth JR, Jin S, Judge RA, Madar DJ, Park C.-P, Park C.-M, Petros AM, Tse C, Rosenberg SH, Elmore SW. Bioorg. Med. Chem. Lett. 2010; 20: 7503
- 14a Olesen S.-P, Waetjen F. US 5200422, 1993
- 14b Taliani S, Pugliesi I, Barresi E, Simorini F, Salerno S, La Motta C, Marini AM, Cosimelli B, Cosconati S, Di Maro S, Marinelli L, Daniele S, Trincavelli ML, Greco G, Novellino E, Martini C, Da Settimo F. J. Med. Chem. 2012; 55: 1490
- 15a Sasmal PK, Sasmal S, Rao PT, Venkatesham B, Roshaiah M, Abbineni C, Khanna I, Jadhav VP, Suresh J, Talwar R, Muzeeb S, Receveur J.-M, Frimurer TM, Rist Ø, Elster L, Högberg T. Bioorg. Med. Chem. Lett. 2010; 20: 5443
- 15b Receveur J.-M, Bjurling E, Christensen A, Högberg T. WO 2006010446, 2006
- 15c Berst F, Furet P, Marzinzik A. WO 2011157787, 2011
- 15d Zhang P, Terefenko EA, McComas CC, Mahaney PE, Vu A, Trybulski E, Koury E, Johnston G, Bray J, Deecher D. Bioorg. Med. Chem. Lett. 2008; 18: 6067
- 15e Itoh F, Sasaki S, Miazaki J, Suzuki N. EP 1810677 A1, 2007
- 15f Troisi L, Granito C, Perrone S, Rosato F. Tetrahedron Lett. 2011; 52: 4330
- 16a Tipparaju SK, Muench SP, Mui EJ, Ruzheinikov SN, Lu JZ, Hutson SL, Kirisits MJ, Prigge ST, Roberts CW, Henriquez FL, Kozikowski AP, Rice DW, McLeod RL. J. Med. Chem. 2010; 53: 6287
- 16b Smallheer JM, Alexander RS, Wang J, Wang S, Nakajima S, Rossi KA, Smallwood A, Barbera F, Burdick D, Luettgen JM, Knabb RM, Wexler RR, Jadhav PK. Bioorg. Med. Chem. Lett. 2004; 14: 5263
- 17a Chen L, Dillon MP, Feng L, Yang M. US 2010324069, 2010
- 17b Badarau E, Suzenet F, Bojarski AJ, Fînaru A.-L, Guillaumet G. Bioorg. Med. Chem. Lett. 2009; 19: 1600
- 17c Lam PY. S, Vincent G, Clark CG, Deudon S, Jadhav PK. Tetrahedron Lett. 2001; 42: 3415
- 18 Bianchi M, Butti A, Rossi F, Barzaghi F, Marcaria F. Eur. J. Med. Chem. 1981; 16: 321
- 19 Olesen S.-P, Jensen LM, Moldt P. US 5475015, 1993
- 20 Moran O, Galietta LJ, Zegerra-Moran O. Cell. Mol. Life Sci. 2005; 62: 446
- 21 Molina P, Alajarin M, Arques A. Synthesis 1982; 596