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Synthesis 2013; 45(10): 1387-1405
DOI: 10.1055/s-0032-1316906
DOI: 10.1055/s-0032-1316906
paper
Selective Sequential Cross-Coupling Reactions on Imidazole towards Neurodazine and Analogues
Further Information
Publication History
Received: 03 December 2012
Accepted after revision: 20 March 2013
Publication Date:
04 April 2013 (online)
![](https://www.thieme-connect.de/media/synthesis/201310/lookinside/thumbnails/10.1055-s-0032-1316906-1.jpg)
Abstract
Polysubstituted imidazoles represent a common structural motif in bioactive molecules. A modular and flexible strategy towards 2,4,5-triarylated imidazoles is reported applying a Suzuki–Miyaura cross-coupling protocol. Employing 1-protected 2,4,5-tribromoimidazole as starting material, both stepwise and one-pot protocols towards the title compounds are disclosed. The utility of the approach was demonstrated by synthesizing neurodazine, a biologically active molecule affecting neuronal cell differentiation.
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References
- 1a Baumann M, Baxendale IR, Ley SV, Nikbin N. Beilstein J. Org. Chem. 2011; 7: 442
- 1b Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry and Biochemistry and the Role of Heterocycles in Science, Technology, Medicine, and Agriculture. Pozharsky AF, Soldatenkov AT, Katritzky AR. Wiley; Chichester: 1997
- 1c Kosjek T, Heath E. Top. Heterocycl. Chem. 2012; 27: 219
- 2a Bellus D. Lect. Heterocycl. Chem. 1987; 9: 65
- 2b Beier C, Benting J, Coqueron P.-Y, Dunkel R, Greul J, Grosjean-Cournoyer M.-C, Hadano H, Rinolfi P, Vors J.-P. PCT Int. Appl WO 2010055114 A1 20100520, 2010 ; Chem. Abstr. 2010, 152, 592056.
- 2c Dumeunier R, Lamberth C, Trah S, Wendeborn S. PCT Int. Appl WO 2009053102 A1 20090430, 2009 ; Chem. Abstr. 2009, 150, 494866.
- 3a Muller T, Braese S. Angew. Chem. Int. Ed. 2011; 50: 11844
- 3b Rasmussen SC, Schwiderski RL, Mulholland ME. Chem. Commun. 2011; 47: 11394
- 3c Maly KE. J. Mater. Chem. 2009; 19: 1781
- 3d Elbing M, Bazan GC. Angew. Chem. Int. Ed. 2008; 47: 834
- 4a Jin Z. Nat. Prod. Rep. 2011; 28: 1143
- 4b Koswatta PB, Lovely CJ. Nat. Prod. Rep. 2011; 28: 511
- 4c Sawaya AC. H. F, Abreu IN, Andreazza NL, Eberlin MN, Mazzafera P In Alkaloids: Properties, Application and Pharmacological Effects. Cassiano NM. Nova Science Publishers Inc.; Hauppauge N.Y.: 2010: 63-80
- 5a Boehm JC, Smietana JM, Sorenson ME, Garigipati RS, Gallagher TF, Sheldrake PL, Bradbeer J, Badger AM, Laydon JT, Lee JC, Hillegass LM, Griswold DE, Breton JJ, Chabot-Fletcher MC, Adams JL. J. Med. Chem. 1996; 39: 3929
- 5b Biradar JS, Mugali PS, Somappa SB, Rajesab P. Org. Chem. Indian J. 2008; 4: 408
- 6a Williams DR, Lee M.-R, Song Y.-A, Ko S.-K, Kim G.-H, Shin I. J. Am. Chem. Soc. 2007; 129: 9258
- 6b Williams DR, Kim G.-H, Lee M.-R, Shin I. Nat. Protoc. 2008; 3: 835
- 6c Shin I.-J, Lee M.-R, Williams D. PCT Int. Appl WO 2007061153 A1 20070531, 2007 ; Chem. Abstr. 2007, 147, 9916.
- 7a Takahashi K, Yamanaka S. Cell 2006; 126: 663
- 7b Maherali N, Hochedlinger K. Cell Stem Cell 2008; 3: 595
- 7c Lowry WE, Richter L, Yachechko R, Pyle AD, Tchieu J, Sridharan R, Clark AT, Plath K. Proc. Natl. Acad. Sci. U.S.A. 2008; 105: 2883
- 7d Park IH, Zhao R, West JA, Yabuuchi A, Huo H, Ince TA, Lerou PH, Lensch MW, Daley GQ. Nature 2008; 451: 141
- 7e Takahashi K, Tanabe K, Ohnuki M, Narita M, Ichisaka T, Tomoda K, Yamanaka S. Cell 2007; 131: 861
- 7f Yu J, Vodyanik MA, Smuga-Otto K, Antosiewicz-Bourget J, Frane JL, Tian S, Nie J, Jonsdottir GA, Ruotti V, Stewart R, Slukvin II, Thomson JA. Science 2007; 318: 1917
- 8a For reviews, see: Zhu S, Wurdak H, Schultz PG. Future Med. Chem. 2010; 2: 965
- 8b Lyssiotis CA, Lairson LL, Boitano AE, Wurdak H, Zhu S, Schultz PG. Angew. Chem. Int. Ed. 2011; 50: 200
- 8c Lo KW-H, Ashe KM, Kan HM, Laurencin CT. Regener. Med. 2012; 7: 535
- 8d Song H, Chang W, Song B.-W, Hwang K.-C. Am. J. Stem Cells 2012; 1: 22
- 8e Andrews PD. Future Med. Chem. 2011; 3: 1539
- 8f Yuan X, Li W, Ding S. Prog. Drug Res. 2011; 67: 253
- 8g Lukaszewicz AI, McMillan MK, Kahn M. J. Med. Chem. 2010; 53: 3439
- 8h Li W, Ding S. Trends Pharmacol. Sci. 2010; 31: 36
- 9 Grimmett MR In Science of Synthesis. Vol. 12. Neier R. Thieme; Stuttgart: 2002: 325-528
- 10 Samai S, Nandi GC, Singh P, Singh MS. Tetrahedron 2009; 65: 10155
- 11 Lipshutz BH, Hagen W. Tetrahedron Lett. 1992; 33: 5865
- 12a Schnürch M, Flasik R, Khan AF, Spina M, Mihovilovic MD, Stanetty P. Eur. J. Org. Chem. 2006; 3283
- 12b Schroeter S, Stock C, Bach T. Tetrahedron 2005; 61: 2245
- 12c Wang J.-R, Manabe K. Synthesis 2009; 1405
- 12d Djakovitch L, Batail N, Genelot M. Molecules 2011; 16: 5241
- 12e Slagt VF, de Vries AH. M, de Vries JG, Kellogg RM. Org. Process Res. Dev. 2010; 14: 30
- 12f Fairlamb IJ. S. Chem. Soc. Rev. 2007; 36: 1036
- 12g Banwell MG, Goodwin TE, Ng S, Smith JA, Wong DJ. Eur. J. Org. Chem. 2006; 3043
- 13a de Meijere A, von Zezschwitz P, Nuske H, Stulgies B. J. Organomet. Chem. 2002; 653: 129
- 13b Dang TT, Dang TT, Rasool N, Villinger A, Langer P. Adv. Synth. Catal. 2009; 351: 1595
- 13c Neenan TX, Whitesides GM. J. Org. Chem. 1988; 53: 2489
- 13d Eichhorn SH, Paraskos AJ, Kishikawa K, Swager TM. J. Am. Chem. Soc. 2002; 124: 12742
- 13e Toguem S.-MT, Villinger A, Langer P. Synlett 2009; 3311
- 13f Toguem S.-MT, Villinger A, Langer P. Synlett 2010; 909
- 13g Sharif M, Zeeshan M, Reimann S, Villinger A, Langer P. Tetrahedron Lett. 2010; 51: 2810
- 13h Akrawi OA, Hussain M, Langer P. Tetrahedron Lett. 2011; 52: 1093
- 13i Hussain M, Khera RA, Nguyen T.-H, Langer P. Org. Biomol. Chem. 2011; 9: 370
- 13j Zinad DS, Feist H, Villinger A, Langer P. Tetrahedron 2012; 68: 711
- 13k Shibahara F, Yamauchi T, Yamaguchi E, Murai T. J. Org. Chem. 2012; 77: 8815
- 14a Miyaura N, Yamada K, Suzuki A. Tetrahedron Lett. 1979; 36: 3437
-
14b Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
- 15a Langhammer I, Erker T. Heterocycles 2005; 65: 2721
- 15b Skoumbourdis AP, Moore S, Landsman M, Thomas CJ. Tetrahedron Lett. 2007; 48: 9140
- 16a Strotman NA, Chobanian HR, He J, Guo Y, Dormer PG, Jones CM, Steves JE. J. Org. Chem. 2010; 75: 1733
- 16b Kawaski I, Yamashita M, Ohta S. Chem. Pharm. Bull. 1996; 44: 1831
- 17 Huang Z, Jin J, Machajewski TD, Antonios-McCrea WR, McKenna M, Poon D, Renhowe PA, Sendzik M, Shafer CM, Smith A, Xu Y, Zhang Q. PCT Int. Appl WO 2009115572, 2009 ; Chem. Abstr. 2009, 151, 403302.
- 18a Billingsley K, Buchwald SL. J. Am. Chem. Soc. 2007; 129: 3358
- 18b Molander GA, Canturk B, Kennedy LE. J. Org. Chem. 2009; 74: 973
- 19 Greene TW, Wuts PG. M. Protective Groups in Organic Synthesis. 3rd ed. Wiley-Interscience; New York: 1999
- 20 Felix AM, Heimer EP, Lambros TJ, Tzougraki C, Meienhofer J. J. Org. Chem. 1978; 43: 4194
- 21 Haddach AA, Kelleman A, Deaton-Rewolinski MV. Tetrahedron Lett. 2002; 43: 399
- 22 Whitten JP, Matthews DP, McCarthy JR. J. Org. Chem. 1986; 51: 1891
- 23 Iddon B, Khan N, Lim BL. J. Chem. Soc., Chem. Commun. 1985; 1428
- 24 Langhammer I, Erker T. Heterocycles 2005; 65: 1975
- 25 Wang B, Sun H.-X, Sun Z.-H, Lin G.-Q. Adv. Synth. Catal. 2009; 351: 415
- 26 Revesz L, Bonne F, Makavou P. Tetrahedron Lett. 1998; 39: 5171
- 27 Hasaninejad A, Zare A, Shekouhy M, Ameri Rad J. J. Comb. Chem. 2010; 12: 844
- 28 Ucucu U, Karaburun NG, Isikdag I. Farmaco 2001; 56: 285
- 29 Siddiqui SA, Narkhede UC, Palimkar SS, Daniel T, Lahoti RJ, Srinivasan KV. Tetrahedron 2005; 61: 3539
- 30a Wolkenberg SE, Wisnoski DD, Leister WH, Wang Y, Zhao Z, Lindsley CW. Org. Lett. 2004; 6: 1453
- 30b Shaabani A, Maleki A, Behnam M. Synth. Commun. 2009; 39: 102
- 31 Puratchikody A, Gopalakrishnan S, Nallu M. Indian J. Pharm. Sci. 2005; 67: 725
- 32 Jadhav SD, Kokare ND, Jadhav SD. J. Heterocycl. Chem. 2008; 45: 1461
- 33 Patel A, Bures F, Ludwig M, Kulhanek J, Pytela O, Ruzicka A. Heterocycles 2009; 78: 999
For reviews on cross-coupling on heterocyclic substrates, see: