Reactions of 1-Methylpyrrole Derivatives by Benzyne

Ju-Hyun Song; Eon-Jin Lee; Yeon-Geun Kwon; Dai-Il Jung; Jung-Tai Hahn

doi:10.14233/ajchem.2015.18884

Issue

Vol. 27 No. 8 (2015): Vol 27 Issue 8

Issue Published : April 27, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Reactions of 1-Methylpyrrole Derivatives by Benzyne

https://doi.org/10.14233/ajchem.2015.18884

Ju-Hyun Song

Department of Chemistry, Dong-A University, Nakdong-Daero 550beon-gil, Saha-gu, Busan 604-714, Republic of Korea

Eon-Jin Lee

Department of Chemistry, Dong-A University, Nakdong-Daero 550beon-gil, Saha-gu, Busan 604-714, Republic of Korea

Yeon-Geun Kwon

Department of Chemistry, Dong-A University, Nakdong-Daero 550beon-gil, Saha-gu, Busan 604-714, Republic of Korea

Dai-Il Jung

Department of Chemistry, Dong-A University, Nakdong-Daero 550beon-gil, Saha-gu, Busan 604-714, Republic of Korea

Jung-Tai Hahn

Department of Beautycare, Young-Dong University, Chungchengbuk-do 370-701, Republic of Korea

Corresponding Author(s) : Dai-Il Jung

dijung@dau.ac.kr

Asian Journal of Chemistry, Vol. 27 No. 8 (2015): Vol 27 Issue 8
Article Published : April 28, 2015

Abstract

In general, benzyne is known that it reacts additionally by using-additional reaction on electrophilicity and pyrrole derivatives causes Diel-Alder reaction or Michael type addition reaction. Our study synthesized various Michael-type adducts 3a,b, 4a,b, 8 by the reaction of 1-methylpyrroles and dimethyl acetylenedicarboxylate (DMAD) (or diethyl acetylenedicarboxylate or diethyl azodicarboxylate) with AlCl₃ as a acid-catalyst. We have performed benzyne chemistry of 2- or 3-substituted pyrroles. Products are 6a-d. Those results indicate that due to electrophilicity of benzyne, a wide variety of anionic and unchanged nucleophilic readily add to pyrrole to generate substituted pyrroles.

Keywords

Pyrrole Benzyne Diels-Alder reaction Michael-type reaction Electrophilicity

Song, J.-H., Lee, E.-J., Kwon, Y.-G., Jung, D.-I., & Hahn, J.-T. (2015). Reactions of 1-Methylpyrrole Derivatives by Benzyne. Asian Journal of Chemistry, 27(8), 3079–3082. https://doi.org/10.14233/ajchem.2015.18884

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References

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References

M.E. Hayes, H. Shinokubo and R.L. Danheiser, Org. Lett., 7, 3917 (2005); doi:10.1021/ol051372l.

U.K. Tambar and B.M. Stoltz, J. Am. Chem. Soc., 127, 5340 (2005); doi:10.1021/ja050859m.

R.W. Hoffimann, Dehydrobenzene and Cycloalkynes, Academic Press: New York (1967).

E.R. Biehl and S.P. Khanapure, Acc. Chem. Res., 22, 275 (1989); doi:10.1021/ar00164a003.

S.V. Kessar, in eds.: B.M. Trost and I. Fleming, Comprehensive Organic Synthesis; Pergamon Press: New York, Vol. 4, pp. 483-515 (1991).

S.L. Buchward and R.D. Broene, in eds.: E.W. Able, F.G.A. Stone and G. Willkinson, Comprehensive Organometallic Chemistry II; Pergamon Press: Oxford, UK, Vol. 12, pp. 771-784 (1995).

H. Pellissier and M. Santelli, Tetrahedron, 59, 701 (2003); doi:10.1016/S0040-4020(02)01563-6.

H.H. Wenk, M. Winkler and W. Sander, Angew. Chem. Int. Ed., 42, 502 (2003); doi:10.1002/anie.200390151.

I.I. Schuster, L. Craciun, D.M. Ho and R.A. Pascal Jr., Tetrahedron, 58, 8875 (2002); doi:10.1016/S0040-4020(02)01054-2.

H.M. Duong, M. Bendikov, D. Steiger, Q. Zhang, G. Sonmez, J. Yamada and F. Wudl, Org. Lett., 5, 4433 (2003); doi:10.1021/ol035751v.

J. Lu, D.M. Ho, N.J. Vogelaar, C.M. Kraml and R.A. Pascal, J. Am. Chem. Soc., 126, 11168 (2004); doi:10.1021/ja046576w.

J. Ikadai, H. Yoshida, J. Ohshita and A. Kunai, Chem. Lett., 34, 56 (2005); doi:10.1246/cl.2005.56.

M.E. Hayes, H. Shinokubo and R.L. Danheiser, Org. Lett., 7, 3917 (2005); doi:10.1021/ol051372l.

C. Dockendorff, S. Sahli, M. Olsen, L. Milhau and M. Lautens, J. Am. Chem. Soc., 127, 15028 (2005); doi:10.1021/ja055498p.

Z.J. Liu and R.C. Larock, J. Org. Chem., 71, 3198 (2006); doi:10.1021/jo0602221.

H. Yoshida, M. Watanabe, J. Ohshita and A. Kunai, Chem. Commun., 3292 (2005); doi:10.1039/b505392g.

H. Yoshida, M. Watanabe, J. Ohshita and A. Kunai, Tetrahedron Lett., 46, 6729 (2005); doi:10.1016/j.tetlet.2005.07.119.

D.I. Jung, Y.Y. Kim, B.G. Yoo, Y.G. Lee and S.K. Choi, J. Korean Chem. Soc., 37, 982 (1993).

Issue

Vol. 27 No. 8 (2015): Vol 27 Issue 8

Reactions of 1-Methylpyrrole Derivatives by Benzyne

Corresponding Author(s) : Dai-Il Jung

Abstract

Keywords

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