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(04): 535-540
DOI: 10.1055/s-0035-1560965
DOI: 10.1055/s-0035-1560965
paper
Rapid Synthesis of Functionalized (1-Benzo[d]thiazol-2-ylimidazolidin-4-ylidene)acetates and (1-Thiazol-2-ylimidazolidin-4-ylidene)acetates via a Three-Component Reaction
Further Information
Publication History
Received: 24 July 2015
Accepted after revision: 23 October 2015
Publication Date:
11 January 2016 (online)
Abstract
A simple synthetic protocol was developed for the efficient synthesis of functionalized (1-benzo[d]thiazol-2-ylimidazolidin-4-ylidene)acetates via a three-component reaction among 2-aminobenzothiazole, α,β-unsaturated N-arylaldimines, and dialkyl acetylenedicarboxylates in anhydrous dichloromethane at room temperature. Additionally, the three-component reaction with 2-aminothiazole afforded the corresponding (1-thiazol-2-ylimidazolidin-4-ylidene)acetates.
Key words
heterocycles - imidazoles - electron-deficient alkynes - benzothiazoles - multicomponent reactionsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560965.
- Supporting Information
-
References
- 1a Greenhill JV, Lue P. Prog. Med. Chem. 1993; 30: 203
- 1b Sullivan JD, Giles RL, Looper RE. Curr. Bioact. Compd. 2009; 5: 39
- 1c Iradyan MA, Iradyan NS, Arsenyan FG, Stepanyan GM. Pharm. Chem. J. 2009; 43: 439
- 2a Kobayashi J, Ishibashi M. Alkaloids 1992; 41: 41
- 2b Kobayashi J, Ishibashi M. Compr. Nat. Prod. Chem. 1999; 8: 415
- 2c Blunt JW, Copp BR, Keyzers RA. Nat. Prod. Rep. 2013; 30: 237
- 2d Berlinck RG. S, Burtoloso AC. B, Silva AE, Romminger S, Morais RP, Bandeira K, Mizuno CM. Nat. Prod. Rep. 2012; 29: 1382
- 3a Luca LD. Curr. Med. Chem. 2006; 13: 1
- 3b Bhandari K, Srinivas N, Keshava GB. S, Shukla PK. Eur. J. Med. Chem. 2009; 44: 437
- 4a Niwano Y, Seo A, Kanai K, Hamaguchi H, Uchida K, Yamaguchi H. Antimicrob. Agents Chemother. 1994; 38: 2204
- 4b Di Santo R, Tafi A, Costi R, Botta M, Artico M, Corelli F, Forte M, Caporuscio F, Angiolella L, Palamara AT. J. Med. Chem. 2005; 48: 5140
- 4c Saha AK, Liu L, Simoneaux RL, Kukla MJ, Marichal P, Odds F. Bioorg. Med. Chem. Lett. 2000; 10: 2175
- 5a Congiu C, Cocco MT, Onnis V. Bioorg. Med. Chem. Lett. 2008; 18: 989
- 5b Venkatesan AM, Agarwal A, Abe T, Ushirogochi HO, Santos D, Li Z, Francisco G, Lin YI, Peterson PJ, Yang Y, Weiss WJ, Shales DM, Mansour TS. Bioorg. Med. Chem. 2008; 16: 1890
- 5c Nakamura T, Kakinuma H, Umemiya H, Amada H, Miyata N, Taniguchi K, Bando K, Sato M. Bioorg. Med. Chem. Lett. 2004; 14: 333
- 6a Han MS, Kim DH. Bioorg. Med. Chem. Lett. 2001; 11: 1425
- 6b Roman G, Riley JG, Vlahakis JZ, Kinobe RT, Brien JF, Nakatsu K, Szarek WA. Bioorg. Med. Chem. 2007; 15: 3225
- 6c Bbizhayev MA. Life Sci. 2006; 78: 2343
- 7 Welton T. Chem. Rev. 1999; 99: 2071
-
8 Herrmann WA. Angew. Chem. Int. Ed. 2002; 41: 1290
- 9a Grimmett MR In Comprehensive Heterocyclic Chemistry . Vol. 5. Katritzky AR, Rees CW. Pergamon; Oxford: 1984: 469
- 9b Grimmett MR In Comprehensive Heterocyclic Chemistry II . Vol. 3. Katritzky AR, Scriven EF. V. Pergamon; Oxford: 1996: 77
- 9c Grimmett MR. Imidazole Benzimidazole Synthesis . Academic Press; San Diego: 1997
- 10a Bellina F, Cauteruccio S, Rossi R. Tetrahedron 2007; 63: 4571
- 10b Senra JD, Aguiar LC. S, Simas AB. C. Curr. Org. Synth. 2011; 8: 53
- 10c Karimi AR, Bayat F. Tetrahedron Lett. 2013; 54: 45
- 10d Wang F, Tran-Dubé M, Scales S, Johnson S, McAlpine I, Ninkovic S. Tetrahedron Lett. 2013; 54: 4054
- 10e Gogoia A, Sarmah G, Dewan A, Bora U. Tetrahedron Lett. 2014; 55: 31
- 10f Yoon YK, Ali MA, Wei AC, Choon TS, Osman H. Tetrahedron Lett. 2014; 55: 4697
- 10g Patel M, Saunthawal RK, Verma AK. Tetrahedron Lett. 2014; 55: 1310
- 11a Nelson SF. J. Org. Chem. 1969; 34: 2248
- 11b Murphy ST, Taylor WC, Vadasz A. Aust. J. Chem. 1982; 35: 1215
-
11c Galliford CV, Scheidt KA. J. Org. Chem. 2007; 72: 1811
- 11d Kikuchi S, Iwai M, Murayama H, Fukuzawa S. Tetrahedron Lett. 2008; 49: 114
- 11e Rajasekaran T, Karthik G, Sridhar B, Subba Reddy BV. Org. Lett. 2013; 15: 1512
- 12a Li YF, Shi J, Wu ZG, Wang XL, Wu XW, Gu JC, Bu HZ, Ma HF. Tetrahedron 2014; 70: 2472
- 12b Li YF, Wu ZG, Shi J, Pan Y, Bu HZ, Ma HF, Gu JC, Huang H, Wang YZ, Wu L. Tetrahedron 2014; 70: 8971
- 13a Lei M, Zhan ZJ, Tian W, Lu P. Tetrahedron 2012; 68: 3361
- 13b Lei M, Tian W, Li W, Lu P, Wang YG. Tetrahedron 2014; 70: 3665
- 14a Zhang J, Yan CG. Eur. J. Org. Chem. 2014; 5598
- 14b Zhang J, Sun J, Yan CG. RSC Adv. 2015; 5: 82324
- 14c Zhang J, Yan CG. Tetrahedron 2015; 71: 6681
- 15 Arab-Salmanabdadi S, Dorvar M, Notash B. Tetrahedron 2015; 71: 1292
- 16a Hou H, Zhang Y, Yan CG. Chem. Commun. 2012; 48: 4492
- 16b Sun J, Sun Y, Gong H, Xie YJ, Yan CG. Org. Lett. 2012; 14: 5172
- 16c Han Y, Sun Y, Sun J, Yan CG. Tetrahedron 2012; 68: 8256
- 16d Sun J, Sun Y, Gao H, Yan C. Eur. J. Org. Chem. 2012; 1976
- 16e Wu L, Sun J, Yan CG. Org. Biomol. Chem. 2012; 10: 9452
- 16f Sun J, Xie YJ, Yan CG. J. Org. Chem. 2013; 78: 8354
- 16g Gao H, Sun J, Yan CG. Tetrahedron 2013; 69: 589
- 16h Sun J, Zhu D, Gong H, Yan CG. Tetrahedron 2013; 69: 10565
- 17a Gao H, Sun J, Yan CG. J. Org. Chem. 2014; 79: 4131
- 17b Han Y, Sheng YJ, Yan CG. Org. Lett. 2014; 16: 2654
- 17c Gong H, Sun J, Yan CG. Synthesis 2014; 46: 489
- 17d Xie YJ, Sun J, Yan CG. ACS Comb. Sci. 2014; 16: 271
- 17e Zhang LJ, Yan CG. Mol. Diversity 2014; 18: 787
- 17f Zhang J, Gao H, Sun J, Yan CG. Eur. J. Org. Chem. 2014; 5598
- 17g Lu LJ, Yan CG. Tetrahedron 2014; 70: 9587
- 17h Zhu D, Sun J, Yan CG. Synthesis 2015; 47: 193
- 17i Yang F, Sun J, Gao H, Yan CG. RSC Adv. 2015; 5: 32786
- 17j Sun J, Chen L, Gong H, Yan CG. Org. Biomol. Chem. 2015; 13: 5905
- 18 CCDC 1407940 contains the supplementary crystallographic data for compound 1b in this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.