Preparation of 2-substituted pyrroles and indoles by regioselective alkylation and deprotection of 1- (2-trimethylsilylethoxymethyl) pyrrole and 1- (2-trimethylsilylethoxymethyl) indole
Edwards, M.P.; Doherty, A.M.; Ley, S.V.; Organ, H.M.
Tetrahedron (Oxford. Print) 42(13): 3723-3729
1986
ISSN/ISBN: 0040-4020 Accession: 077347443
PDF emailed within 1 workday: $29.90
Related References
Edwards, M.P.; Doherty, A.M.; Ley, S.V.; Organ, H.M. 1986: Preparation of 2 substituted pyrroles and indoles by regioselective alkylation and deprotection of 1 2 trimethylsilylethoxymethyl pyrrole and 1 2 trimethylsilyethoxymethyl indole Tetrahedron 42(13): 3723-3729Binder, J.; Zbiral, E. 1984: Diethyl[trimethylsilylethoxymethyl]phosphonat: ein neuartiges Reagens für variable Aufbaustrategien von Carbonyl-, α-Hydroxycarbonyl Verbindungen und Vinylphosphonaten - Le triméthylsilyléthoxyméthyl phosphonate de diéthyle: un nouveau réactif pour des stratégies de construction variables de composés carbonylés, α-hydroxycarbonylés et de vinyl phosphonates - Diethyl [trimethylsilylethoxymethyl] phosphonate: a new reagent for variable preparation methods of carbonyl-, α-hydroxycarbonyl compounds and vinylphosphonates Tetrahedron Letters 25(38): 4213-4216
Yu, C.H.E.N.; Imrie, C.T.; Cooper, J.M.; Glidle, A.; Morris, D.G.; Ryder, K.S. 1998: Structure and conductivity in substituted polypyrroles. Part 1. Synthesis and electropolymerization of N-trimethylsilylethoxymethyl-3-methyl-4-pyrrole carboxylate ethyl ester Polymer International 47(1): 43-49
Chandra, T.; Broderick, W.E.; Broderick, J.B. 2010: An efficient deprotection of N-trimethylsilylethoxymethyl (SEM) groups from dinucleosides and dinucleotides Nucleosides Nucleotides and Nucleic Acids 29(2): 132-143
Wei, H.-Z.; Yu, L.-Z.; Shi, M. 2019: Lewis or Brønsted acid-catalysed reaction of propargylic alcohol-tethered alkylidenecyclopropanes with indoles and pyrroles for the preparation of polycyclic compounds tethered with indole or pyrrole motif Organic and Biomolecular Chemistry 18(1): 135-139
Logusch, E.W. 1984: Use of a β-trimethylsilylethoxymethyl ester as a protecting group: a facile preparation of 1-hydroxycyclopropanecarboxylic acid phosphate Tetrahedron Letters 25(38): 4195-4198
Bach, T.; Jiao, L. 2013: Regioselective Direct C–H Alkylation of NH Indoles and Pyrroles by a Palladium/Norbornene-Cocatalyzed Process Synthesis 46(01): 35-41
Sakurai, N.; Ohmiya, S. 1993: Photoaddition reaction of 1,2-dialkyl-indoles and -pyrroles to 1-methyl-2-pyridone via proton transfer from the 2-methylene group of the indole or pyrrole Journal of the Chemical Society. Chemical Communications (3): 297-298
Nair, R.N.; Bannister, T.D. 2015: One-pot directed alkylation/deprotection strategy for the synthesis of substituted pyrrole[3,4-d]pyridazinones European Journal of Organic Chemistry 8: 1764-1770
Guadarrama-Morales, O.; Méndez, F.; Miranda, L.D. 2007: Highly regioselective radical alkylation of 3-substituted pyrroles Tetrahedron Letters 48(26): 4515-4518
Yadav, J.; Reddy, B.; Reddy, P.; Srinivas, C. 2002: Zinc-mediated Barbier reactions of pyrrole and indoles: a new method for the alkylation of pyrrole and indoles Tetrahedron Letters 43(29): 5185-5187
Unangst, P.C.; Brown, R.E. 1984: Indole esters as heterocyclic synthons. II: Preparation of 1,3-oxazino[5,6-b]indoles and 3-substituted-pyrano[3,2-b]indoles Journal of Heterocyclic Chemistry 21(2): 283-288
Agarwal, S.K.; Saxena, A.K.; Anand, N. 1981: A Convenient Method for Indole N-Alkylation in Substituted Pyrazino[2′,1′:6,1]pyrido[3,4-b]indoles Synthesis 06: 465-466
Lipshutz, B.H.; Vaccaro, W.; Huff, B. 1986: Protection of imidazoles as their β-trimethylsilylethoxymethyl (SEM) derivatives Tetrahedron Letters 27(35): 4095-4098
Wang, W.; Liu, X.; Cao, W.; Wang, J.; Lin, L.; Feng, X. 2010: Highly enantioselective synthesis of beta-heteroaryl-substituted dihydrochalcones through Friedel-Crafts alkylation of indoles and pyrrole Chemistry 16(5): 1664-1669
Huff, B. 1986: Protection of imidazoles as their beta trimethylsilylethoxymethyl derivatives Tetrahedron Letters: 4095-4098
Kanaoka, Y.; Miyashita, K.; Yonemitsu, O. 1969: 3H-indoles--II. Synthesis of 3-alkyl-3H indoles by the alkylation of 2,3-disubstituted indoles with polyphosphate ester and some reactions of the 3H-indole system Tetrahedron 25(14): 2757-2766
Chaudhary, B.; Diwaker, M.; Sharma, S. 2018: Regioselective indole C2-alkylation using β-CF3-substituted enones under redox neutral Rh(iii) catalysis Organic Chemistry Frontiers 5(21): 3133-3137
Palacios, Francisco; Aparicio, Domitila; De-Los-Santos, Jesus, M.; Vicario, Javier 2001: Regioselective alkylation reactions of hydrazones derived from phosphine oxides and phosphonates. Synthesis of phosphorus substituted 1-amino-pyrrolones, pyridinones and pyrroles Tetrahedron 57(10): 1961-1972, 3 March
Crich, D.; Lim, L.B.L. 1990: Trimethylsilylethoxymethyl Chloride as a Formaldehyde Equivalent in Aldol-Type Reactions Synlett 1990(2): 117-118