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(03): 413-420
DOI: 10.1055/s-0035-1560973
DOI: 10.1055/s-0035-1560973
paper
Transition-Metal-Free Synthesis of Indolizines from Electron-Deficient Alkenes via One-Pot Reaction Using TEMPO as an Oxidant
Further Information
Publication History
Received: 10 September 2015
Accepted after revision: 30 October 2015
Publication Date:
19 November 2015 (online)
Abstract
A one-pot method for the synthesis of multisubstituted indolizines from α-halo carbonyl compounds, pyridines, and electron-deficient alkenes is reported. The oxidative dehydrogenation reaction takes place under transition-metal-free conditions using TEMPO as an oxidant. This protocol uses ready available starting materials in a convenient procedure under mild reaction conditions.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560973.
- Supporting Information
-
References
- 1a Xu Z, Xu L. ChemSusChem 2015; 8: 2176
- 1b Bernoud E, Lepori C, Mellah M, Schulz E, Hannedouche J. Catal. Sci. Technol. 2015; 5: 2017
-
1c Sun C, Shi Z. Chem. Rev. 2014; 114: 9219
- 1d Chen K, Zhang P, Wang Y, Li H. Green Chem. 2014; 16: 2344
- 1e Coeffard V, Moreau X, Thomassigny C, Greck C. Angew. Chem. Int. Ed. 2013; 52: 5684
-
1f Bhunia A, Yetra SR, Biju AT. Chem. Soc. Rev. 2012; 41: 3140
- 2a Flisch W In Comprehensive Heterocyclic Chemistry . Vol. 4. Katritzky AR, Rees CW. Pergamon; Oxford: 1984: 476
- 2b Ewing J, Hughes GK, Ritchie E, Taylor WC. Nature (London) 1952; 169: 618
- 2c Reimann E. Prog. Chem. Org. Nat. Prod. 2007; 88: 1
-
2d Michael JP. Nat. Prod. Rep. 2008; 25: 139
- 2e Michael JP. Nat. Prod. Rep. 2003; 20: 458
- 2f Daly JW, Spande TF, Garraffo HM. J. Nat. Prod. 2005; 68: 1556
- 2g Lebceuf M, Cave A, Ranaivo A, Moskowitz H. Can. J. Chem. 1989; 67: 947
- 2h Snyder SA, ElSohly AM, Kontes F. Angew. Chem. Int. Ed. 2010; 49: 9693
- 3a Ghosh AK, Bilcer G, Schiltz G. Synthesis 2001; 2203
- 3b List B, Castello C. Synlett 2001; 1687
- 3c Sonnet P, Dallemagne P, Guillon J, Enguehard C, Stiebing S, Tanguy J, Bureau R, Rault S, Auvray P, Moslemi S, Sourdaine P, Seralini GE. Bioorg. Med. Chem. 2000; 8: 945
- 3d Ostby OB, Dalhus B, Gundersen L.-L, Rise F, Bast A, Haenen GR. M. M. Eur. J. Org. Chem. 2000; 3763
- 3e Maryanoff BE, Vaught JL, Shank RP, McComsey DF, Costanzo MJ, Nortey SO. J. Med. Chem. 1990; 33: 2793
-
3f Lillelund VH, Jensen HH, Liang X, Bols M. Chem. Rev. 2002; 102: 515
- 3g Gubin J, Vogelaer HD, Inion H, Houben C, Lucchetti J, Mahaux J, Rosseels G, Peiren M, Clinet M, Polster P, Chatelain P. J. Med. Chem. 1993; 36: 1425
- 3h Bermudez J, Fake CS, Joiner GF, Joiner KA, King FD, Miner WD, Sanger GJ. J. Med. Chem. 1990; 33: 1924
- 4a Vlahovici A, Andrei M, Druta I. J. Lumin. 2002; 96: 279
- 4b Vlahovici A, Druta I, Andrei M, Cotlet M, Dinica R. J. Lumin. 1999; 82: 155
- 4c Mitsumori T, Bendikov M, Dautel O, Wudl F, Shioya T, Sato H, Sato Y. J. Am. Chem. Soc. 2004; 126: 16793
- 4d Saeva FD, Luss HR. J. Org. Chem. 1988; 53: 1804
- 4e Sonnenschein H, Henrich G, Resch-Genger U, Schulz B. Dyes Pigm. 2000; 46: 23
- 4f Retaru AV, Druta LD, Deser T, Mueller TJ. Helv. Chim. Acta 2005; 88: 1798
- 4g Delattre F, Woisel P, Surpateanu G, Cazier F, Blach P. Tetrahedron 2005; 61: 3939
- 4h Mitsumori T, Campos LM, Garcia-Garibay MA, Wudl F, Sato H, Sato Y. J. Mater. Chem. 2009; 19: 5826
- 5a Liu R, Hong J, Lu C, Xu M, Gao J, Jia Y. Org. Lett. 2015; 17: 3050
- 5b Albaladejo MJ, Alonso F, Gonzalez-Soria MJ. ACS Catal. 2015; 5: 3446
- 5c Tang S, Liu K, Long Y, Qi X, Lan Y, Lei A. Chem. Commun. 2015; 51: 8769
- 5d Liu R, Lu C, Zhang M, Gao J, Jia Y. Chem. Eur. J. 2015; 21: 7057
- 5e Zhang L, Li X, Liu Y, Zhang D. Chem. Commun. 2015; 51: 6633
- 5f Zhang K, Wang H, Zheng J, Yu L, Ding H. Chem. Commun. 2015; 51: 6399
- 5g Kim E, Lee Y, Lee S, Park SB. Acc. Chem. Res. 2015; 48: 538
- 5h Amaral MF. Z. J, Baumgartner AA, Vessecchi R, Clososki GC. Org. Lett. 2015; 17: 238
- 5i Liu J, Zhou L, Ye W, Wang C. Chem. Commun. 2014; 50: 9068
- 5j Gao M, Tian J, Lei A. Chem. Asian J. 2014; 9: 2068
- 5k Wang X, Li S, Pan Y, Wang H, Liang H, Chen Z, Qin X. Org. Lett. 2014; 16: 580
- 6a Dawood KM, Ragab EA, Khedr NA. J. Chin. Chem. Soc. (Taipei, Taiwan) 2009; 56: 1180
- 6b Darwish ES. Molecules 2008; 13: 1066 ; http://www.mdpi.com/journal/molecules
- 6c Kheder NA, Darwish ES, Dawood KM. Heterocycles 2009; 78: 177
- 6d Shen Y.-M, Wang B.-X, Feng Y.-Y, Shen Z.-Y, Shen J, Li C, Hu H.-W. Gaodeng Xuexiao Huaxue Xuebao 2006; 27: 651
- 6e Tanaka A, Usui T. Chem. Pharm. Bull. 1979; 27: 3078
- 6f Wang B.-X, Hu H.-W. Gaodeng Xuexiao Huaxue Xuebao 2004; 25: 273
- 6g Tominaga Y, Hidaki S, Matsuda Y, Kobayashi G, Sakemi K. Yakugaku Zasshi 1979; 99: 540
- 6h Hu H, Feng J, Zhu Y, Gu N, Kan Y. RSC Adv. 2012; 2: 8637
- 6i Wang C, Hu H, Xu J, Kan W. RSC Adv. 2015; 5: 41255
- 6j Liu Y, Zhang Y, Shen Y, Hu H, Xu J. Org. Biomol. Chem. 2010; 8: 2449
- 7a Mallat T, Baiker A. Chem. Rev. 2004; 104: 3037
- 7b Wertz S, Studer A. Green Chem. 2013; 15: 3116
- 7c Campbell AN, Stahl SS. Acc. Chem. Res. 2012; 45: 851
- 7d Schultz MJ, Sigman MS. Tetrahedron 2006; 62: 8227
- 7e Zhan B, Thompson A. Tetrahedron 2004; 60: 2917
- 7f Zhang J, Jiang Z, Zhao D, He G, Zhou S, Han S. Chin. J. Chem. 2013; 31: 794
- 7g Murarka S, Wertz S, Studer A. Chimia 2012; 66: 413
- 8a Hu H, Shi K, Hou R, Zhang Z, Zhu Y, Zhou J. Synthesis 2010; 4007
- 8b Liu Y, Hu H, Zhang Y, Hu H, Xu J. Org. Biomol. Chem. 2010; 8: 4921
- 8c Hu H, Liu Y, Zhong H, Zhu Y, Wang C, Ji M. Chem. Asian J. 2012; 7: 884
- 8d Liu Y, Hu H, Su X, Sun J, Cao C, Shi Y. Eur. J. Org. Chem. 2013; 2020
- 8e Hu H, Liu Y, Xu J, Kan Y, Wang C, Ji M. RSC Adv. 2014; 4: 24389
- 8f Li G, Hu H, Kan Y, Ma K. Chin. J. Org. Chem. 2014; 34: 903
- 8g Sun J, Hu H, Wang F, Wu H, Liu Y. RSC Adv. 2014; 4: 36498
- 8h Sun J, Wang F, Hu H, Wang X, Wu H, Liu Y. J. Org. Chem. 2014; 79: 3992
- 8i Wang F, Shen Y, Hu H, Wang X, Wu H, Liu Y. J. Org. Chem. 2014; 79: 9556
- 8j Hu H, Li G, Hu W, Liu Y, Wang X, Kan Y, Ji M. Org. Lett. 2015; 17: 1114
- 9a Bobbitt JM, Bruckner C, Merbouh N. Org. React. 2009; 74: 103
- 9b Bobbitt JM, Flores M, Cecile L. Heterocycles 1988; 27: 509
- 9c Shibuya M, Tomizawa M, Iwabuchi Y. J. Org. Chem. 2008; 73: 4750
- 10 Allgäuer DS, Mayr H. Eur. J. Org. Chem. 2014; 2956
Selected recent reviews for transition-metal-free reactions:
Selected recent articles for the synthesis of indolizines:
Selected reviews for TEMPO as oxidant or catalyst for oxidation: