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

Evgeny Kh. Sadykov; Natalya A. Lobanova; Valery K. Stankevich

doi:10.1055/s-0034-1378940

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(05): 672-678
DOI: 10.1055/s-0034-1378940

paper

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

Authors

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

Abstract

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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.

Key words

acetylene - addition - alcohol - pyrrole - vinyl ether

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Referenzen

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

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