Synthesis 2015; 47(05): 672-678
DOI: 10.1055/s-0034-1378940
paper
© Georg Thieme Verlag Stuttgart · New York

Base-Mediated Addition of 1-(2-Hydroxyalkyl)pyrroles to Acetylene: Atom-Economic Route to 1-[2-(Vinyloxy)alkyl]pyrroles

Evgeny Kh. Sadykov*
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: esad@irioch.irk.ru
,
Natalya A. Lobanova
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: esad@irioch.irk.ru
,
Valery K. Stankevich
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: esad@irioch.irk.ru
› Author Affiliations
Further Information

Publication History

Received: 05 August 2014

Accepted after revision: 06 November 2014

Publication Date:
15 December 2014 (eFirst)

Abstract

Nucleophilic addition of 1-(2-hydroxyalkyl)pyrroles to acetylene, an unactivated carbon–carbon triple bond, in the presence of a base has been studied. As a result an atom-economic synthetic method to obtain 1-[2-(vinyloxy)alkyl]pyrroles in good yields employing superbase, sodium or potassium hydroxide in dimethyl sulfoxide, systems has been developed. 1-[2-(Vinyloxy)alkyl]pyrroles are cleaved by base with the elimination of vinyl alcohol to give 1-vinylpyrroles.

Supporting Information

 
  • References

  • 1 Rehbein J, Hiersemann M. Synthesis 2013; 45: 1121
    • 2a Takaya J, Miyashita Y, Kusama H, Iwasawa N. Tetrahedron 2011; 67: 4455
    • 2b Bigdeli MA, Halimehjani AZ, Mohammadipour M, Sagharichi P. J. Heterocycl. Chem. 2012; 49: 926
    • 2c Quadrelli P, Lunghi F, Bovio B, Gautschi W, Caramella P. Eur. J. Org. Chem. 2012; 1418
    • 3a Davies HM. L, Hu B. J. Org. Chem. 1992; 57: 3186
    • 3b Davies HM. L, Kong N, Churchill MR. J. Org. Chem. 1998; 63: 6586
    • 3c Panne P, DeAngelis A, Fox JM. Org. Lett. 2008; 10: 2987
    • 3d Tzimopoulos D, Brenna S, Czapik A, Gdaniec M, Ardizzoia A, Akrivos PD. Inorg. Chim. Acta 2012; 383: 105
    • 4a Kim JJ, Alper H. Chem. Commun. 2005; 3059
    • 4b Cai C, Yu S, Cao B, Zhang X. Chem. Eur. J. 2012; 18: 9992
    • 4c Chikkali SH, Bellini R, de Bruin B, van der Vlugt JI, Reek JN. H. J. Am. Chem. Soc. 2012; 134: 6607
    • 4d Franke R, Selent D, Börner A. Chem. Rev. 2012; 112: 5675
    • 5a Alcaide B, Almendros P, Luna A. Chem. Rev. 2009; 109: 3817
    • 5b Castagnolo D, Botta L, Botta M. J. Org. Chem. 2009; 74: 3172
    • 5c Lozano-Vila AM, Monsaert S, Bajek A, Verpoort F. Chem. Rev. 2010; 110: 4865
    • 5d Evano G, Gaumont A.-C, Alayrac C, Wrona IE, Giguere JR, Delacroix O, Bayle A, Jouvin K, Theunissen C, Gatignol J, Silvanus AC. Tetrahedron 2014; 70: 1529
    • 6a Gøgsig TM, Kleimark J, NilssonLill SO, Korsager S, Lindhardt AT, Norrby P.-O, Skrydstrup T. J. Am. Chem. Soc. 2012; 134: 443
    • 6b Ruan J, Xiao J. Acc. Chem. Res. 2011; 44: 614
    • 6c Schranck J, Wu X.-F, Neumann H, Beller M. Chem. Eur. J. 2012; 18: 4827
    • 6d Xie Y, Hu J, Xie P, Qian B, Huang H. J. Am. Chem. Soc. 2013; 135: 18327
    • 7a Fan H, Peng J, Hamann MT, Hu J.-F. Chem. Rev. 2008; 108: 264
    • 7b Young IS, Thornton PD, Thompson A. Nat. Prod. Rep. 2010; 27: 1801
    • 8a Baumann M, Baxendale IR, Ley SV, Nikbin N. Beilstein J. Org. Chem. 2011; 7: 442
    • 8b Wang M.-Z, Xu H, Liu T.-W, Feng Q, Yu S.-J, Wang S.-H, Li Z.-M. Eur. J. Med. Chem. 2011; 46: 1463
    • 8c Mohamed MS, Kamel R, Fatahala SS. Eur. J. Med. Chem. 2011; 46: 3022
    • 8d SerraMoreno J, Agas D, Sabbieti MG, Di Magno M, Migliorini A, Loreto MA. Eur. J. Med. Chem. 2012; 57: 391
    • 8e Gomha SM, Eldebss TM. A, Abdulla MM, Mayhoub AS. Eur. J. Med. Chem. 2014; 82: 472
    • 8f Pagadala LR, Mukkara LD, Singireddi S, Singh A, Thummaluru VR, Jagarlamudi PS, Guttala RS, Perumal Y, Dharmarajan S, Upadhyayula SM, Ummanni R, Basireddy VS. R, Ravirala N. Eur. J. Med. Chem. 2014; 84: 118
    • 9a Tat’yana VV, Oleg NE. Russ. Chem. Rev. 1997; 66: 443
    • 9b Bengü B, Toppare L, Kalaycioglu E. Des. Monomers Polym. 2001; 4: 53
    • 9c Ateh DD, Navsaria HA, Vadgama P. J. R. Soc., Interface 2006; 3: 741
    • 9d Kopecka J, Kopecky D, Vrnata M, Fitl P, Stejskal J, Trchova M, Bober P, Moravkova Z, Prokes J, Sapurina I. RSC Adv. 2014; 4: 1551
    • 9e Omastová M, Mičušík M. Chem. Pap. 2012; 66: 392
    • 9f Wang J.-G, Wei B, Kang F. RSC Adv. 2014; 4: 199
  • 10 Ates M. Mater. Sci. Eng., C 2013; 33: 1853
  • 11 Yue Z, Lisdat F, Parak WJ, Hickey SG, Tu L, Sabir N, Dorfs D, Bigall NC. ACS Appl. Mater. Interfaces 2013; 5: 2800
  • 12 Dufresne S, Skene WG. J. Phys. Org. Chem. 2012; 25: 211
  • 13 Tsuchida E, Tomono T, Honda K. J. Polym. Sci., Polym. Chem. Ed. 1973; 11: 853
    • 14a Nedolya NA, Tarasova OA, Albanov AI, Trofimov BA. Tetrahedron Lett. 2010; 51: 5316
    • 14b Klyba LV, Nedolya NA, Tarasova OA, Sanzheeva ER. Russ. J. Org. Chem. 2014; 50: 35
  • 15 Winternheimer DJ, Shade RE, Merlic CA. Synthesis 2010; 2497
  • 16 Trotuş I.-T, Zimmermann T, Schüth F. Chem. Rev. 2014; 114: 1761
  • 17 Trofimov BA. Curr. Org. Chem. 2002; 6: 1121
  • 18 Kukharev BF, Stankevich VK, Kukhareva VA. Russ. J. Org. Chem. 2011; 47: 614
  • 19 Aleskerov MA, Sergei SY, Kucherov VF. Russ. Chem. Rev. 1978; 47: 134
  • 20 Purification of Laboratory Chemicals . 6th ed.; Armarego WL. F, Chai CL. L. Butterworth-Heinemann; Oxford: 2009
  • 21 Sadykov EKh, Stankevich VK, Lobanova NA, Klimenko GR. Russ. J. Org. Chem. 2014; 50: 219
  • 22 Schiffner JA, Wöste TH, Oestreich M. Eur. J. Org. Chem. 2010; 174
  • 23 Schwetlick K. Organikum . Wiley-VCH; Weinheim: 2004