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Rearrangement and Degradation of 3a,7a-Dihydroindole Esters
Corresponding Author(s) : Do-Hun Lee
Asian Journal of Chemistry,
Vol. 28 No. 1 (2016): Vol 28 Issue 1
Abstract
The purpose of this paper is to report that pyrroles 1a-c also gave the 1:2 adducts 3a-c when refluxed with dimethyl acetylene dicarboxylate in ether (or ether with AlCl3) and rearrangement and degradation of 3a,7a-dihydroindole esters 3a-c as 1:2 molar [4+2] cycloadducts were investigated. The electrons in compound 3a are assumed to move as in its resonance structure A which should results in the formation of transition state B. Next, cleavage of the C-C bond between the carbonyl carbon atom and the 3a carbon atom and the 1,3-shift of the hydrogen atom from 7a position into 2 position will occur easily to form an aromatized stable indole compound 4a.
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- J. Juselius and D. Sundholm, Phys. Chem. Chem. Phys., 2, 2145 (2000); doi:10.1039/b000260g.
- E. Fischer, Sugar and Purine Syntheses, Nobel Prize Lecture (1902).
- R.A. Jones and G.P. Bean, The Chemistry of Pyrroles, Academic Press, New York, p. 146 and 256 (1977).
- R.M. Acheson and J.M. Vernon, J. Chem. Soc., 1148 (1962); doi:10.1039/jr9620001148.
- R.M. Acheson and J.M. Vernon, J. Chem. Soc., 1008 (1963); doi:10.1039/jr9630001008.
- T. Ohe, K. Ohe, S. Uemura and N. Sugita, J. Organomet. Chem., 344, C5 (1988); doi:10.1016/0022-328X(88)80220-1.
- P. Scheiner, J.H. Schomaker, S. Deming, W.J. Libbey and G.P. Nowack, J. Am. Chem. Soc., 87, 306 (1965); doi:10.1021/ja01080a030.
- J.H. Hall, F.E. Behr and R.L. Reed, J. Am. Chem. Soc., 94, 4952 (1972); doi:10.1021/ja00769a027.
- E.M. Kosower, Physical Organic Chemistry, Wiley: New York, Part I (1968).
- A.A. Frost and R.G. Pearson, Kinetics and Mechanism, Wiley: New York, Chp. 7, edn 2 (1961).
References
J. Juselius and D. Sundholm, Phys. Chem. Chem. Phys., 2, 2145 (2000); doi:10.1039/b000260g.
E. Fischer, Sugar and Purine Syntheses, Nobel Prize Lecture (1902).
R.A. Jones and G.P. Bean, The Chemistry of Pyrroles, Academic Press, New York, p. 146 and 256 (1977).
R.M. Acheson and J.M. Vernon, J. Chem. Soc., 1148 (1962); doi:10.1039/jr9620001148.
R.M. Acheson and J.M. Vernon, J. Chem. Soc., 1008 (1963); doi:10.1039/jr9630001008.
T. Ohe, K. Ohe, S. Uemura and N. Sugita, J. Organomet. Chem., 344, C5 (1988); doi:10.1016/0022-328X(88)80220-1.
P. Scheiner, J.H. Schomaker, S. Deming, W.J. Libbey and G.P. Nowack, J. Am. Chem. Soc., 87, 306 (1965); doi:10.1021/ja01080a030.
J.H. Hall, F.E. Behr and R.L. Reed, J. Am. Chem. Soc., 94, 4952 (1972); doi:10.1021/ja00769a027.
E.M. Kosower, Physical Organic Chemistry, Wiley: New York, Part I (1968).
A.A. Frost and R.G. Pearson, Kinetics and Mechanism, Wiley: New York, Chp. 7, edn 2 (1961).