Synthesis 2019; 51(20): 3825-3833
DOI: 10.1055/s-0039-1690003
paper
© Georg Thieme Verlag Stuttgart · New York

Regioselective Synthesis of 2-Acylbutadienes from β,γ-Unsaturated Ketones

Dmitrii A. Shabalin
,
Elena V. Ivanova
,
Igor A. Ushakov
,
Elena Yu. Schmidt
,
Boris A. Trofimov
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St, Irkutsk 664033, Russian Federation   Email: boris_trofimov@irioch.irk.ru
› Author Affiliations
The reported study was funded by RFBR according to the research project No. 18-33-00100.
Further Information

Publication History

Received: 28 May 2019

Accepted after revision: 26 June 2019

Publication Date:
15 July 2019 (online)


Abstract

2-Acylbuta-1,3-dienes have been synthesized regioselectively from aromatic and heteroaromatic β,γ-unsaturated ketones (readily accessible via base-catalyzed addition of ketones to acetylenes) and aldehydes. The reaction smoothly proceeds with piperidine (10 mol%)/acetic acid (10 mol%) catalytic pair in boiling toluene to provide synthetically attractive polyconjugated electron-deficient dienes in up to 94% yield.

Supporting Information

 
  • References

    • 1a Clarke PA, Santos S, Martin WH. C. Green Chem. 2007; 9: 438
    • 1b Xiang H, Chen Y, He Q, Xie Y, Yang C. RSC Adv. 2013; 3: 5807
    • 2a Trofimov BA, Schmidt EYu, Ushakov IA, Zorina NV, Skital’tseva EV, Protsuk NI, Mikhaleva AI. Chem. Eur. J. 2010; 16: 8516
    • 2b Trofimov BA, Schmidt EYu, Zorina NV, Ivanova EV, Ushakov IA. J. Org. Chem. 2012; 77: 6880
  • 3 Trofimov BA, Schmidt EYu. Acc. Chem. Res. 2018; 51: 1117 ; and reference cited therein
  • 4 Li H, Yin L. Tetrahedron Lett. 2018; 59: 4121
    • 5a Zhu B, Zhang W, Lee R, Han Zh, Yang W, Tan D, Huang K.-W, Jiang Zh. Angew. Chem. Int. Ed. 2013; 52: 6666
    • 5b Jing Zh, Bai X, Chen W, Zhang G, Zhu B, Jiang Zh. Org. Lett. 2016; 18: 260
    • 5c Han M.-Y, Luan W.-Y, Mai P.-L, Li P, Wang L. J. Org. Chem. 2018; 83: 1518
    • 6a Qiao B, Huang Y.-J, Nie J, Ma J.-A. Org. Lett. 2015; 17: 4608
    • 6b Zhang H.-J, Shi C.-Y, Zhong F, Yin L. J. Am. Chem. Soc. 2017; 139: 2196
    • 7a Gu Y, Wang Y, Yu T.-Y, Liang Y.-M, Xu P.-F. Angew. Chem. Int. Ed. 2014; 53: 14128
    • 7b Zhan G, He Q, Yuan X, Chen Y.-C. Org. Lett. 2014; 16: 6000
    • 7c Iriarte I, Olaizola O, Vera S, Gamboa I, Oiarbide M, Palomo C. Angew. Chem. Int. Ed. 2017; 56: 8860
    • 7d Akula PS, Hong B.-C, Lee G.-H. Org. Lett. 2018; 20: 7835
  • 8 Kong X, Song J, Liu J, Meng M, Yang S, Zeng M, Zhan X, Li C, Fang X. Chem. Commun. 2018; 54: 4266
  • 9 Sudhakar G, Raghavaiah J, Mahesh G, Singarapu KK. Org. Biomol. Chem. 2016; 14: 2866
    • 10a Jones G. Org. React. (N.Y.) 1967; 15: 204
    • 10b Tietze LF, Beifuss U. The Knoevenagel Condensation . In Comprehensive Organic Synthesis, Vol. 2. Trost BM, Fleming I, Heathcock CH. Pergamon Press; Oxford: 1991. Chap. 1.11, 341-394
  • 11 Schmidt EYu, Ivanova EV, Tatarinova IV, Ushakov IA, Semenova NV, Vashchenko AV, Trofimov BA. Org. Lett. 2016; 18: 2158
  • 12 Zaid Y, Mboyi CD, Drapeau MP, Radal L, Chahdi FO, Rodi YK, Ollevier T, Taillefer M. Org. Lett. 2019; 21: 1564
  • 13 Vasil’ev AA, Serebryakov EP. Russ. Chem. Rev. 2001; 70: 735
  • 14 Mavrov MV, Kucherov VF. Russ. Chem. Bull. 1962; 11: 1190
    • 15a Lantzsch R, Arlt D. Liebigs Ann. Chem. 1976; 1757
    • 15b Honek JF, Mancini ML, Belleau B. Synth. Commun. 1984; 14: 483
    • 15c Hoffmann HM. R, Eggert U, Poly W. Angew. Chem., Int. Ed. Engl. 1987; 26: 1015
    • 16a Franck-Neumann M, Martina D, Brion F. Angew. Chem., Int. Ed. Engl. 1981; 20: 864
    • 16b Colson PJ, Franck-Neumann M, Sedrati M. Tetrahedron Lett. 1989; 30: 2393
  • 17 Maercker A, van de Flierdt J, Girreser U. Tetrahedron 2000; 56: 3373
  • 18 Matsubara S, Ukai K, Toda N, Utimoto K, Oshima K. Synlett 2000; 995
  • 19 Nativi C, Taddei M, Mann A. Tetrahedron 1989; 45: 1131
  • 20 Choi SY, Chung YK. Adv. Synth. Catal. 2011; 353: 2609