Metalation of Azines and Diazines by Philippe C. Gros (auth.), Michael Schnürch, Marko D.

By Philippe C. Gros (auth.), Michael Schnürch, Marko D. Mihovilovic (eds.)

Reactions of Pyridines, Benzopyridines and Azapyridines with Organomagnesiums and Organolithiums, via Manfred Schlosser

Lithiations and Magnesiations on Quinoline and Isoquinoline, through Floris Chevallier, Florence Mongin

Metalation Reactions of Pyridines, Quinolines, and Isoquinolines with Ate Bases and Their Alkali steel Salt-Modified Congeners, through Costa Metallinos, Kathryn Stromski

Lithiations and Grignard Reactions on Pyrimidine and Quinazoline, by means of Andrej Kolarovic

Other Stoichiometric Metalation Reactions on Pyrimidine and Quinazoline, via Philippe C. Gros

Metalation of Pyrazine and Quinoxaline, via Nelly Plé1, Corinne Fruit

Metalation of Pyridazine, Cinnoline, and Phtalazine, by way of Ernst Horkel

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Abbreviations Ac aq Bn BOM Bu Bz Cbz concd dba DME DMF DMSO E+ equiv h HMPA i-Pr LDA LHMDS LTMP LUMO min MOM NIS NMP PMB rt s satd s-Bu TBAI TBDMS t-Bu TDS Acetyl Aqueous Benzyl Benzyloxymethyl Butyl Benzoyl Benzyloxycarbonyl Concentrated Dibenzylideneacetone Dimethoxyethane Dimethylformamide Dimethyl sulfoxide Electrophile Equivalent(s) Hour(s) Hexamethylphosphoric triamide Isopropyl Lithium diisopropylamide Lithium bis(trimethylsilyl)amide Lithium 2,2,6,6-tetramethylpiperidide Lowest unoccupied molecular orbital Minute(s) Methoxymethyl N-Iodosuccinimide N-Methyl-2-pyrrolidinone 4-Methoxyphenyl Room temperature Second(s) Saturated sec-Butyl Tetrabutylammonium iodide tert-Butyldimethylsilyl tert-Butyl Dimethyl-(2,3-dimethylbut-2-yl)silyl (thexyl-dimethylsilyl) 39 46 46 55 57 61 61 Lithiations and Grignard Reactions on Pyrimidine and Quinazoline THF THP TIPS TMEDA TMP TMS Tr 23 Tetrahydrofuran Tetrahydropyran-2-yl Triisopropylsilyl N,N,N0 ,N0 -Tetramethyl-1,2-ethylenediamine 2,2,6,6-Tetramethylpiperidyl Trimethylsilyl Triphenylmethyl 1 Introduction Pyrimidines comprise an important class of heterocyclic compounds, with numerous applications in medicinal and agricultural chemistry [1].

References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Abbreviations Ac aq Bn BOM Bu Bz Cbz concd dba DME DMF DMSO E+ equiv h HMPA i-Pr LDA LHMDS LTMP LUMO min MOM NIS NMP PMB rt s satd s-Bu TBAI TBDMS t-Bu TDS Acetyl Aqueous Benzyl Benzyloxymethyl Butyl Benzoyl Benzyloxycarbonyl Concentrated Dibenzylideneacetone Dimethoxyethane Dimethylformamide Dimethyl sulfoxide Electrophile Equivalent(s) Hour(s) Hexamethylphosphoric triamide Isopropyl Lithium diisopropylamide Lithium bis(trimethylsilyl)amide Lithium 2,2,6,6-tetramethylpiperidide Lowest unoccupied molecular orbital Minute(s) Methoxymethyl N-Iodosuccinimide N-Methyl-2-pyrrolidinone 4-Methoxyphenyl Room temperature Second(s) Saturated sec-Butyl Tetrabutylammonium iodide tert-Butyldimethylsilyl tert-Butyl Dimethyl-(2,3-dimethylbut-2-yl)silyl (thexyl-dimethylsilyl) 39 46 46 55 57 61 61 Lithiations and Grignard Reactions on Pyrimidine and Quinazoline THF THP TIPS TMEDA TMP TMS Tr 23 Tetrahydrofuran Tetrahydropyran-2-yl Triisopropylsilyl N,N,N0 ,N0 -Tetramethyl-1,2-ethylenediamine 2,2,6,6-Tetramethylpiperidyl Trimethylsilyl Triphenylmethyl 1 Introduction Pyrimidines comprise an important class of heterocyclic compounds, with numerous applications in medicinal and agricultural chemistry [1].

1 C-Deprotonative Lithiations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2 Lithiations and Grignard Reactions by Halogen–Metal Exchange . . . . . . . . . 7 Quinazolines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8 Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

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