Tandem allylic isomerization IMDAF reaction in the synthesis 5,6,7-substituted indoles. Research Topic Seminar Jie Xu
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1 Tandem allylic isomerization IMDAF reaction in the synthesis 5,6,7-substituted indoles Research Topic Seminar Jie Xu Jie Wipf Group Page 1 of 35 6/7/2011
2 Contents! Introduction of indoles! Preparation and functionalization of indoles! Amino furan cycloaddition! Summary and acknowledgement Jie Wipf Group Page 2 of 35 6/7/2011
3 Contents! Introduction of indoles! Preparation and functionalization of indoles! Amino furan cycloaddtion! Summary and acknowledgement Jie Wipf Group Page 3 of 35 6/7/2011
4 General Properties Indole and the simple alkyl indoles are colorless crystalline solids With a range of odours from naphthalene-like to faecal Many simple indoles are available commercially and produced by synthesis Most indoles are quite stable in air with the exception of those which carry a simple alkyl group at C-2 Joule, J.A.; Mills, K. in Heterocyclic Chemistry (5th Edition), Wiley, Hoboken, N.J., Jie Wipf Group Page 4 of 35 6/7/2011
5 History Indole = indigo + oleum 1869: Propose the formula of indole Which is generally accepted today Adolf von Baeyer The Nobel Prize in Chemistry 1905 In recognition of his services in the advancement of organic chemistry and the chemical industry, through his work on organic dyes and hydroaromatic compounds". Baeyer, A. Chem. Ber. 1868, 1, 17. Bayer, A. Chem. Ber. 1869, 2, 679. Jie Wipf Group Page 5 of 35 6/7/2011
6 Reserpine Isolated in 1952 India snake root R. serpentina Benth. One of the first drugs for the treatment of diseases of the central nervous system (CNS) such as anxiety and mental disorders. Approved: June 20, 1960 Chen, F. R; Huang, J. Chem. Rev. 2005, 105, Jie Wipf Group Page 6 of 35 6/7/2011
7 Bioactive Indole! Tryptophan, tryptamine, auxins, Essential Amino Acid Neurotransmitter Neurotransmitter Hallucinogen Plant hormone Jie Wipf Group Page 7 of 35 6/7/2011
8 Natural Indole Alkaloid Ergolines Psychedelic drugs β-carbolines CNS drugs Yohimbine Stimulant drugs Kratom alkaloids Psych stimulant Strynos nux-vomica alkaloids Toxic pesticide Iboga alkaloids Psychoactive drugs Vinca alkaloids Anti-mitotic & anti-microtubule agents Kawasaki, T.; Higuchi, K. Nat. Prod. Rep. 2005, 22, 761. Ishikura, M.; Yamada, K. Nat. Prod. Rep. 2009, 26, 803. Jie Wipf Group Page 8 of 35 6/7/2011
9 Top 200 brand-name drugs in 2009 Drugs with indole or indoline cores Jie Wipf Group Page 9 of 35 6/7/2011
10 Biological Activity! Enzyme inhibitors!!! HMG-CoA Reductase Inhibitors Cyclooxygenase Inhibitors Phosphodiesterase (PDE) Inhibitors! Bio receptor Modulators!! 5-Hydroxytryptamine (5-HT) Receptors Cannabinoid Receptors Representative interactions of indole ligands respectively at serotonin 5-HT6 (A) and melanocortin-4 (B) receptors. Fraga, C. et al. Mini-Rev. in Med. Chem. 2009, 9, 782. Jie Wipf Group HMG-CoA Reductase Inhibitors Page 10 of 35 6/7/2011
11 Broad Spectrum of Application Agrochemicals Pigments Pharmaceuticals Fragrances Jie Wipf Group Material Science Page 11 of 35 6/7/2011
12 Statics! Number of publications (limited to letters and review articles) focusing on indole (SciFinder Scholar). The inset shows the number of publications dealing with the synthesis or functionalization of indoles ( ). Bandini, M.; Eichholzer, A. Angew. Chem. Int. Ed. 2009, 48, Jie Wipf Group Page 12 of 35 6/7/2011
13 Contents! Introduction to indoles! Preparation and functionalization of indoles! Amino furan cycloaddtion! Summary and acknowledgement Jie Wipf Group Page 13 of 35 6/7/2011
14 Syntheis Indoles from pyrroles Aryne intermediates Sigmatropic rearrangements Cycloaddition and electrocyclization Nucleophilic cyclization Metal-catalyzed indole syntheses Electrophilic cyclization Radical cyclization Oxidative cyclization Reductive cyclization Jie Wipf Group Page 14 of 35 6/7/2011
15 Cyclization! Nucleophilic Madelung, Schmid, Wender, Couture, Smith, Kihara Nenitzescu, Engler, Bailey Liebeskind, Wright, Saegusa Madelung, W. Ber, 1912, 45, 1128.! Electrophilic Bischler, Nordlander, Cadogan Sundberg, Sundberg, Hemetsberger, Quéguiner, Iwao, Magnus, Feldman Moody, C. J.; Swann, E. Synlett, 1998, 135. Jie Wipf Group Page 15 of 35 6/7/2011
16 Cyclization! Reductive Reissert, Leimgruber Batcho, Makosza Lobachevsky, P. et al. Aust. J. Chem. 1998, 51, 243. Makosza. M.; Stalewski, J. Synthesis, 1997, 1131! Oxidative Watanabe, Knölker! Radical Tin-mediated cyclization Samarium-mediated cyclization Murphy indole-indoline synthesis Ohta, A. et al. Tetrahedron Lett. 1996, 37, Kobayashi, S. et al. Tetrahedron Lett. 1999, 40, Jie Wipf Group Page 16 of 35 6/7/2011
17 Sigmatropic Rearrangements! Fischer, Gassman, Bartoli, Thyagarajan, Julia Fischer indole synthesis Prominent role as a route to indoles, both new and old, and to the large-scale production of indole pharmaceutical intermediates. Gribble, G. J. Chem. Soc., Perkin Trans. 1, 2000, Robinson, B., The Fischer Indole Synthesis, Wiley-Interscience, New York, Jie Wipf Group Page 17 of 35 6/7/2011
18 Cycloaddition and Electrocyclization! Diels Alder cycloaddition Padwa, A.; Dimitroff, M.; Waterson, A. G.; Wu, T. J. Org. Chem. 1998, 63, 3986.! Chapman photocyclization Ibrahim-Ouali, M.; Sinibaldi, M. E.; Troin, Y.; Guillaume D.; Gramain, J. C. Tetrahedron, 1997, 53, Jie Wipf Group Page 18 of 35 6/7/2011
19 Indoles from Pyrroles Natsume indole synthesis Utsunomiya, I.; Muratake, H.; Natsume, M. Chem. Pharm. Bull. 1995, 43, 37. Aryne intermediates Hardcastle, I. R.; Hunter, R. F.; Quayle, P.; Edwards, P. N. Tetrahedron Lett., 1994, 35, Jie Wipf Group Page 19 of 35 6/7/2011
20 Metal-catalyzed indole syntheses! Pd Hegedus Mori Heck indole synthesis Yamanaka Sakamoto indole synthesis Larock indole synthesis! Rh, Ru, Ti (Fürstner), Zr, Cu (Castro), Cr, Mo Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, Gribble, G. J. Chem. Soc., Perkin Trans. 1, 2000, Jie Wipf Group Page 20 of 35 6/7/2011
21 Functionalization of indole Reaction with CC Multiple bond Diels- Alder Reactions Indole Reaction with carbonyl groups Reations at C(sp3) atoms Arylation Vinylation Bandini, M.; Eichholzer, A. Angew. Chem. Int. Ed. 2009, 48, 9608 Jie Wipf Group Page 21 of 35 6/7/2011
22 Chemical Properties Basicity pka (H 2 O) = K eq = 10-6 Oxidation of indole Electron rich nature Electrophilic substitution C times reactive than benzene Jie Wipf Group Page 22 of 35 6/7/2011
23 Functionalization of indole! Reaction with CC Multiple bond! Reations at C(sp 3 ) atoms! Reaction with carbonyl groups Bandini, M.; Eichholzer, A. Angew. Chem. Int. Ed. 2009, 48, 9608 Jie Wipf Group Page 23 of 35 6/7/2011
24 Functionalization of indole! Arylation Vinylation! Diels-Alder Reactions! Reactive in N1, C2, C3 Bandini, M.; Eichholzer, A. Angew. Chem. Int. Ed. 2009, 48, 9608 Jie Wipf Group Page 24 of 35 6/7/2011
25 Contents! Introduction to indoles! Preparation and functionalization of indoles! Amino furan cycloaddition! Summary and acknowledgement Jie Wipf Group Page 25 of 35 6/7/2011
26 Background!! Presence of 4-substitued natural indole compound Lack of effective ways to synthesis 4-substitued indole Petronijevic, F.; Timmons, C.; Cuzzupey, A.; Wipf, P. Chem. Commun. 2009, 104. Jie Wipf Group Page 26 of 35 6/7/2011
27 Amino furan cycloaddition For reviews of IMDAF Kappe, C. O.; Murphree, S. S.; Padwa, A., Tetrahedron, 1997, 53, 14179; Prof. Albert Padwa Emory University Jie Wipf Group Page 27 of 35 6/7/2011
28 Amino furan cycloaddition to indoline! Amino Furan Diels Alder Reaction Padwa, A., et. al., J. Org. Chem., 1997, 62, 2786 ; Padwa, A., et. al., J. Org. Chem.,, 1997, 62, 4088! Thermal or LiClO 4 in ether Padwa, A. et al. J. Org. Chem. 1998, 63, Jie Wipf Group Page 28 of 35 6/7/2011
29 Amino furan cycloaddition to indoline! COOEt more stable than Boc! Br, SPh as leaving group! Alkyne IMDAF! Indoline synthesis Padwa, A. et al. J. Org. Chem. 1999, 64, Jie Wipf Group Page 29 of 35 6/7/2011
30 Amino furan cycloaddition to indoline! DFT calculation of IMDAF with Becke3LYP/6-31G* model Padwa, A. et al. Org. Lett., 2002, 4, 473.! Danishefsky diene to synthesis the precursoe! Carbomethoxy group to activate the olefin! Ergoline intermediate Padwa, A. et al. J. Org. Chem. 2005, 70, Jie Wipf Group Page 30 of 35 6/7/2011
31 Previous Work! Microwave assisted IMDAF! Much fast heating process and less reaction times! Higher temperatures in the pressurized reactor vial! Deprotected indole product rather than protected indoline Petronijevic, F.; Timmons, C.; Cuzzupey, A.; Wipf, P. Chem. Commun. 2009, 104. Jie Wipf Group Page 31 of 35 6/7/2011
32 Methodologies in our group! 3, 4-sustitued by Filip! 5-hydroxy substitued by Ki Bum! 5,6,7-substitued indole Jie Wipf Group Page 32 of 35 6/7/2011
33 Allylic Isomerization! Pd(OAc) 2 catalyst! Internal olefin favored Tsuji, J. et al. Bull. Chem. Soc. Jp. 1976, 49, 1701.! Pd(CH 3 CN) 2 Cl 2 catalyst! 100% conversion of terminal olefin Overman, L. E.; Knoll, F. M. Tetrahedron Lett. 1979, 321.! Pd(CH 3 CN) 2 Cl 2 catalyst! Equilibrium of two internal olefins Nakai, T. et al. Tetrahedron Lett. 1993, 34, Jie Wipf Group Page 33 of 35 6/7/2011
34 Contents! Introduction to indoles! Preparation and functionalization of indoles! Amino furan cycloaddtion! Summary and acknowledgement Jie Wipf Group Page 34 of 35 6/7/2011
35 Acknowledgement! Dr. Wipf! Wipf group members past & present! NMR & MS facilities! NIH, University of Pittsburgh Arts & Science Fellowships Jie Wipf Group Page 35 of 35 6/7/2011
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