Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2016; 48(10): 1437-1456
DOI: 10.1055/s-0035-1560430
DOI: 10.1055/s-0035-1560430
short review
Geminal Bis- and Tristriazoles: Long-known but still Uncommon Heterocyclic Entities
Further Information
Publication History
Received: 09 February 2016
Accepted: 15 February 2016
Publication Date:
22 March 2016 (online)
Abstract
Geminal bis- and tristriazoles belong to a rare and mainly overlooked class of organic compounds with interesting properties. This review summarizes the methods for their preparation. Moreover, applications of these compounds are described, ranging from ring extensions to their use as reactive intermediates for the efficient construction of heterocycles.
1 Introduction
2 Bistriazoles
2.1 Bistriazoles (Tetrahedral Carbon)
2.2 Bistriazoles (Trigonal Carbon)
3 Tristriazoles
4 Conclusion and Prospectives
-
References
- 1a Huisgen R. Proc. Chem. Soc. 1961; 357
- 1b Huisgen R. Angew. Chem. 1963; 75: 604
- 1c Huisgen R, Knorr R, Möbius L, Szeimies G. Chem. Ber. 1965; 98: 4014
- 1d Huisgen R, Knorr R. Naturwissenschaften 1962; 48: 716
-
2a Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
- 2b Tornoe CW, Christensen C, Meldal M. J. Org. Chem. 2002; 67: 3057
- 2c Rademann J, Grøtli M, Meldal M, Bock K. J. Am. Chem. Soc. 1999; 121: 5459
- 2d Wang Q, Chan TR, Hilgraf R, Fokin VV, Sharpless KB, Finn MG. J. Am. Chem. Soc. 2003; 125: 3192
-
2e Chan TR, Hilgraf R, Sharpless KB, Fokin VV. Org. Lett. 2004; 6: 2853
- 2f Wu P, Malkoch M, Hunt JN, Vestberg R, Kaltgrad E, Finn MG, Fokin VV, Sharpless KB, Hawker CJ. Chem. Commun. 2005; 5775
- 2g Evans RA. Aust. J. Chem. 2007; 60: 384
- 3a Thirumurugan P, Matosiuk D, Jozwiak K. Chem. Rev. 2013; 113: 4905
- 3b Tron GC, Pirali T, Billington RA, Canonico PL, Sorba G, Genazzani AA. Med. Res. Rev. 2008; 28: 278
- 3c Kantheti S, Narayan R, Raju KV. S. N. RSC Adv. 2015; 5: 3687
- 4 Häring AP, Kirsch SF. Molecules 2015; 20: 20042 ; http://www.mdpi.com/journal/molecules
- 5 Burckhalter JH, Stephens VC, Hall LA. R. J. Am. Chem. Soc. 1952; 74: 3868
- 6 Katritzky AR, Hughes CV, Rachwal S. J. Heterocycl. Chem. 1989; 26: 1579
- 7 Mukherjee N, Ahammed S, Bhadra S, Ranu BC. Green Chem. 2013; 15: 389
- 8 Sharghi H, Khalifeh R, Doroodmand MM. Adv. Synth. Catal. 2009; 351: 207
- 9 Katritzky AR, Blitzke T, Li J. Synth. Commun. 1996; 26: 3773
- 10 Katritzky AR, Manju K, Steel PJ. J. Org. Chem. 2003; 68: 407
- 11 Zhong Z, Hong R, Wang X. Tetrahedron Lett. 2010; 51: 6763
- 12 Mosslemin MH, Movahhed AE. E-J. Chem. 2012; 9: 301 ; http://www.hindawi.com/journals/jchem/
- 13 Kuang G.-C, Michaels HA, Simmons JT, Clark RJ, Zhu L. J. Org. Chem. 2010; 75: 6540
- 14 Hein JE, Tripp JC, Krasnova LB, Sharpless KB, Fokin VV. Angew. Chem. Int. Ed. 2009; 48: 8018
- 15 Meng J.-C, Fokin VV, Finn MG. Tetrahedron Lett. 2005; 46: 4543
- 16 Rodionov VO, Fokin VV, Finn MG. Angew. Chem. Int. Ed. 2005; 44: 2210
- 17 Erhardt H, Mohr F, Kirsch SF. Chem. Commun. 2016; 52: 545
- 18 Erhardt H, Häring AP, Kotthaus A, Roggel M, Tong ML, Biallas P, Jübermann M, Mohr F, Kirsch SF. J. Org. Chem. 2015; 80: 12460
- 19 Harschneck T, Hummel S, Kirsch SF, Klahn P. Chem. Eur. J. 2012; 18: 1187
- 20 Bredenkamp A, Mohr F, Kirsch SF. Synthesis 2015; 47: 1937
- 21 Okamoto N, Sueda T, Minami H, Miwa Y, Yanada R. Org. Lett. 2015; 17: 1336
- 22 Kamble DA, Karabal PU, Chouthaiwale PV, Sudalai A. Tetrahedron Lett. 2012; 53: 4195
- 23 Chen W, Yan R, Tang D, Guo S, Meng X, Chen B. Tetrahedron 2012; 68: 7956
- 24 Katritzky AR, Wang Z, Wells AP, Steel PJ. Org. Prep. Proced. Int. 1995; 27: 457
- 25 Verma AK, Jha RR, Chaudhary R, Tiwari RK, Danodia AK. Adv. Synth. Catal. 2013; 355: 421
- 26 Katritzky AR, Fali CN, Qi M. Tetrahedron Lett. 1998; 39: 2289
- 27 Katritzky AR, Bobrov S, Kirichenko K, Ji Y. J. Org. Chem. 2004; 69: 303
- 28 Katritzky AR, Bobrov S, Tao H, Kirichenko K. Tetrahedron 2005; 61: 3305
- 29 Petasis NA, Zavialov IA. J. Am. Chem. Soc. 1997; 119: 445
- 30 Staab HA, Seel G. Justus Liebigs. Ann. Chem. 1958; 612: 187
- 31 Katritzky AR, Pleynet DP. M, Yang B. J. Org. Chem. 1997; 62: 4155
- 32 Larsen C, Steliou K, Harpp DN. J. Org. Chem. 1978; 43: 337
- 33 Hubert AJ, Reimlinger H. Chem. Ber. 1970; 103: 2828
- 34 Katritzky AR, Rogovoy BV, Chassaing C, Vvedensky V. J. Org. Chem. 2000; 65: 8080
- 35 Katritzky AR, Khashab NM, Bobrov S, Yoshioka M. J. Org. Chem. 2006; 71: 6753
- 36 Banert K, Richter S, Schaarschmidt D, Lang H. Angew. Chem. Int. Ed. 2013; 52: 3499
- 37 Zapol’skii VA, Namyslo JC, de Meijere A, Kaufmann DE. Beilstein J. Org. Chem. 2012; 8: 621
- 38 Tuyun AF. RSC Adv. 2014; 4: 19640
- 39 Nudelmann NS, Lewkowicz ES, Pérez DG. Synthesis 1990; 917
-
40 Katritzky AR, Ledoux S, Witek RM, Nair SK. J. Org. Chem. 2004; 69: 2976
- 41 Štrukil V, Gracin D, Magdysyuk OV, Dinnebier RE, Friščić T. Angew. Chem. Int. Ed. 2015; 54: 8440
- 42 Katritzky AR, Zhang G.-F, Fan W.-Q, Wu J, Pernak J. J. Phys. Org. Chem. 1993; 6: 567
- 43 Kumar D, Mishra A, Mishra BB, Bhattacharya S, Tiwari VK. J. Org. Chem. 2013; 78: 899
- 44 Kumar D, Mishra BB, Tiwari VK. J. Org. Chem. 2014; 79: 251
- 45 Keri RS, Patil MR, Patil SA, Budagumpi S. Eur. J. Med. Chem. 2015; 89: 207
- 46 Kumar D, Singh AS, Tiwari VK. RSC Adv. 2015; 5: 31584
- 47 Katritzky AR, Rogovoy BV, Kovalenko KV. J. Org. Chem. 2003; 68: 4941
- 48 Kühle E, Anders B, Klauke E, Tarnow H, Zumach G. Angew. Chem., Int. Ed. Engl. 1969; 8: 20
- 49 Ried W, Dietschmann H, Erle H.-E. Synthesis 1980; 619
- 50 Avila L, Elguero J, Juliá S, del Mazo JM. Heterocycles 1983; 20: 1787
- 51 Katritzky AR, Yang Z, Lam JN. Synthesis 1990; 666
- 52 Androsov DA, Neckers DC. J. Org. Chem. 2007; 72: 1148
- 53 Klahn P, Erhardt H, Kotthaus A, Kirsch SF. Angew. Chem. Int. Ed. 2014; 53: 7313
- 54 Olah GA, Ohannesian L, Arvanaghi M. Chem. Rev. 1987; 87: 671
- 55 Katritzky AR, Linghong X. Tetrahedron Lett. 1996; 37: 347
- 56 Katritzky AR, Wu H, Linghong X. Tetrahedron Lett. 1997; 38: 903
For applications of click chemistry in chemical biology, see:
For applications of click chemistry in medicinal chemistry, see:
For applications of click chemistry in materials chemistry, see: