1. Metalation of p-Excessive Heteroaromatics

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1. Metalation of p-Excessive Heteroaromatics

Thermodynamic Acidities of π - Excessive Heteroaromatics References and Notes: Reutov, O.A.; Beletskaya, I.P.; Butin, K.P. CH-acids, Prgamon Press, Oxford, 1978, pp. 67-119.

Kinetic Acidities of π - Excessive Heteroaromatics. References and Notes: Reutov, O.A.; Beletskaya, I.P.; Butin, K.P. CH-acids, Prgamon Press, Oxford, 1978, pp. 67-119. Various authors on Katritzky, A.R,; Rees, C.W. Comprehensive Heterocyclic Chemistry, Pergamon Press, Oxford, 1984, pp 238, 650,771.

Synthetic Use of Metalated non-DMG Furans and Thiophenes. Conversions into other Heterocycles References and Notes: Tetrahedron Lett. 1987, 28, 5791

Synthetic Use of Metalated non-DMG Furans and Thiophenes. Oxidative Pathways References and Notes: Tetrahedron Lett. 1981, 22, 5191. Helv. Chim. Acta. 1985, 68, 2350. Acta Chem. Scand. 1967, 21, 1952; ibid 1972, 26, 31. Review: Gronowitz, S. Hornfeldt, A.-B. in Thiophene and Derivatives, Gronowitz, S. Ed., Wiley, New York, Pt III, 1986 p.24 ff.

Metalated Furans. Additions on Glycosyl Nitrones References and Notes: J. Org. Chem. 1997, 62, 5484

Use of Metalated non-DMG Thiophenes. Historical Industrial Practice References and Notes: Braye, E. Pracor, Paris, France, US 4,127,580, Nov. 28, 1978.

Directed ortho Metalation (DoM) Reactivity of Furans and Thiophenes References and Notes: Org. React. 1979, 26, 1. Organic Sulfur Chemistry 1975, 203. Advan. Heterocyclic Chem. 1981, 30, 167., ibid 1982, 31, 237. Advan. Het. Chem. 1993, 56, 155.

DoM Chemistry of Furans and Thiophenes. Carbon-Based DMG’s. DMG = 2-oxazolino References and Notes: J. Chem Soc. Perkin Trans. I 1985, 2649. J. Org. Chem. 1977, 42, 2649. Tetrahedron 1984, 40, 2107. J. Chem Soc. Perkin Trans. I 1982, 1343.

DoM Chemistry of Furans. DMG = CON-R. Application References and Notes: Tetrahedron Lett. 1988, 29, 741.

DoM Reactivity of Furans and Thiophenes. Dianion Equivalents with Carbon-based DMGs References and Notes: Tetrahedron Lett. 1985, 26, 1149. Tetrahedron Lett. 1985, 26, 5335.

DoM Reactivity of Furans and Thiophenes. “DMG” = CO2- References and Notes: Tetrahedron Lett. 1972, 13, 3507. J. Chem Soc. Perkin Trans. I 1983, 791. Tetrahedron Lett. 1985, 26, 1777. Tetrahedron Lett. 1982, 23, 4127. J. Chem Soc. Perkin Trans. I 1982, 623. J. Chem Soc. Perkin Trans. I 1985, 799. Cuomo, J.; Gee, S.K.; Hartzell, S.C. in Baker, D.R.; Feynes, J.G.; Moberg, W.K. Eds. Synthesis andChemistry of Agrochemicals II, ACS Symposium Series No. 443, ACS Washington, D.C. 1990.

DoM Chemistry of Furans. DMG = CH2O- References and Notes: Tetrahedron Lett. 1983, 24, 5835. Tetrahedron Lett. 1987, 28, 5965. Tetrahedron Lett. 1988, 29, 1247. Tetrahedron Lett. 1989, 30, 1765. Synlett 1991, 33.

DoM Chemistry of Furans and Thiophenes. Heteroatom - Based DMGs, DMG = SO2R References and Notes: Hanagan, M.A. personal communications. Cuomo, J.; Gee, S.K.; Hartzell, S.C. in Baker, D.R.; Feynes, J.G.; Moberg, W.K. Eds. Synthesis and Chemistry of Agrochemicals II, ACS Symposium Series No. 443, ACS Washington, D.C. 1990.

DoM Reactivity of N-DMG Pyrroles References and Notes: Tetrahedron. 1986, 42, 3723. J. Org. Chem. 1989, 54, 203. J. Org. Chem. 1981, 46, 3760.

DoM Reactivity of N-DMG Pyrroles References and Notes: Synthesis 1988, 316. Prog. Heterocyclic Chem. 1989, 1, 1. Org. Prep. Proc. Int.. 1988, 20, 585.

DoM Reactivity of Indoles. N - DMGs References and Notes: a. J. Org. Chem. 1973, 38, 3324. b. Synlett 1991, 289. c. J. Org. Chem. 1993, 58, 1109 and Beak, P. 8th IUPAC Conference on Organic Synthesis, Helsinki, Finland, 1990. d. Tetrahedron Lett. 1985, 26, 5935. e. Tetrahedron Lett. 1987, 28, 3741. f. J. Org. Chem. 1992, 57, 2495 (2-haloindoles). g. Synlett 1990, 313 and references cited therein. h. Heterocycles 1989, 29, 849; J. Org. Chem. 1990, 55, 3688. i. Stoller, A.; Snieckus, V. unpublished results. j. Synthesis 1991, 1079. Fecher, A.; Snieckus, V. unpublished results (2-TMS, 7-deprot) k. Heterocycles 1992, 34, 1295. l. Tetrahedron Lett. 1988, 29, 6429 (ergoline derivatives).

DoM Reactivity of Indoles. N-DMG = CO2t-Bu. Indirect C-7 Substitution References and Notes: Heterocycles 1993, 36, 29.

DoM Reactivity of Indoles. Non-N DMG Indoles. DMG = CONR2 References and Notes: Tetrahedron Lett. 1987, 28, 5259. Synlett 1991, 289. Gribble, G.W. in Advan. Heterocyclic Nat. Prod. Synthesis, Pearson, W.H. Ed. Vol. 1 Jai Press Greenwich, CT., 1991. Wang, X.; Snieckus, V. Unpublished results.

DoM Reactivity of Indoles. Non-N DMG Indoles. DMG = CH2NR2 References and Notes: Synlett 1991, 315. Heterocycles 1992, 34, 1031 Wang, X. Ph.D. Thesis,University ofWaterloo, 1992.

DoM Reactivity of Non-N DMG Indoles. DMG = OCONEt2. Benzenoid Ring Functionalization References and Notes: J. Org. Chem. 1995, 60, 1484.

DoM Reactivity of p-Excessive Heteroaromatics. Pyrrazoles. N DMGs References and Notes: Org. React. 1979, 26, 1. Tetrahedron. 1983, 39, 4133 Prog. Heterocyclic Chem. 1989, 1, 1. Review: Grimmett, M.R.; Iddon, B. Heterocycles 1992, 37, 2087. Synlett 1992, 327. Cuomo, J.; Gee, S.K.; Hartzell, S.C. in Baker, D.R.; Feynes, J.G.; Moberg, W.K. Eds. Synthesis and Chemistry of Agrochemicals II, ACS Symposium Series No. 443, ACS Washington, D.C.1990. .

DoM Reactivity of Pyrrazoles. Non-N DMGs. DMG = SO2N-R References and Notes: Cuomo, J.; Gee, S.K.; Hartzell, S.C. in Baker, D.R.; Feynes, J.G.; Moberg, W.K. Eds. Synthesis and Chemistry of Agrochemicals II, ACS Symposium Series No. 443, ACS Washington, D.C.1990. .

DoM Reactivity of Pyrrazoles. Total Synthesis Application References and Notes: Heterocycles 1982, 19, 1223. .

Metalation Reactivity of Imidazoles References and Notes: Iddon, B. in Kovac, J.; Zalupky, P. Eds. Chemistry of Heterocyclic Compounds Elsevier, Amsterdam, 1988, p.24. Org. React. 1979, 26, 1. Review: Iddon, B.; Ngochindo, R.I. Heterocycles 1994, 38, 2487. .

DoM Reactivity of Imidazoles. DMG = N-SO2NR2. Silicon Protection References and Notes: Synthesis 1991, 1021. J. Chem Soc. Perkin Trans. I 1990, 481.

DoM Reactivity of Imidazoles in Context of Nucleosides References and Notes: Tetrahedron Lett. 1990, 31,1295 and references cited therein. Chem. Pharm. Bull. Jpn. 1983, 31, 787; ibid. 1987, 35, 72. Tetrahedron 1986, 42, 1971.

DoM Reactivity of Oxazoles References and Notes: Tetrahedron Lett. 1981, 22, 3163. Tetrahedron Lett. 1983, 24,2287. Tetrahedron Lett. 1983, 24,4391.

Metalation Reactivity of Thiazoles References and Notes: Reviews: Modern Synthetic Methods, Scheffold, R.Ed, Verlag, Helvetica Chemica Acta, Basel Switzerland, 1992. Dondoni, A., Pure Appl. Chem. 1990, 62, 643. Gazz. Chim. Ital. 1988, 118, 211; Lect. Heterocycl. Chim. 1985, 8, 13. J. Org. Chem. 1989, 54, 693. Tetrahedron Lett. 1989, 30, 6063. Chem. Lett. 1983, 333. Tetrahedron Lett. 1992, 33, 4221. (aminosugars) Tetrahedron Lett. 1993, 34, 619. (Renin inhibitors)

Metalation and DoM Reactivity of Methyl Substituted Oxazoles and Thiazoles References and Notes: Tetrahedron Lett. 1987, 28, 3585.

DoM Reactivity of Aminoisoxazoles References and Notes: Tetrahedron Lett. 1996, 37, 3339

DoM Reactivity of 1-Substituted 1,2,4-Triazoles References and Notes: J. Org. Chem. 1998, 63, 4323