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XXII Table <strong>of</strong> Contents<br />

17.2.1.1.4.1.2.1 Method 1: 1-Hydroxyalkylation <strong>of</strong> Lithio-1,2,3-triazines with<br />

Aromatic Aldehydes ....................................... 246<br />

17.2.1.1.4.1.3 Of Heteroatoms .......................................................... 247<br />

17.2.1.1.4.1.3.1 Method 1: Dehalogenation ........................................... 247<br />

17.2.1.1.4.1.3.2 Method 2: Substitution <strong>of</strong> Halogens by Perfluoroalkyl Groups .......... 248<br />

17.2.1.1.4.1.3.3 Method 3: Substitution <strong>of</strong> Halo-1,2,3-triazines by Hetero Nucleophiles . 249<br />

17.2.1.1.4.1.3.4 Method 4: Hydroxylation <strong>of</strong> 5-Halo-1,2,3-triazines ..................... 250<br />

17.2.1.1.4.1.3.5 Method 5: Replacement <strong>of</strong> Halogen by Alkoxy, Aryloxy, Alkylsulfanyl,<br />

and Dialkylamino Groups .................................. 250<br />

17.2.1.1.4.1.3.6 Method 6: Substitution <strong>of</strong> Alkoxy by Hydrazino Groups ................ 252<br />

17.2.1.1.4.1.3.7 Method 7: Hydrolysis <strong>of</strong> 5-(Dialkylamino)-1,2,3-triazinium Salts ........ 252<br />

17.2.1.1.4.2 Addition Reactions ....................................................... 253<br />

17.2.1.1.4.2.1 Method 1: Protonation <strong>of</strong> 1,2,3-Triazines by Tetrafluoroboric Acid ...... 253<br />

17.2.1.1.4.2.2 Method 2: N-Acylation, N-Alkylation, and N-Arylation ................. 254<br />

17.2.1.1.4.2.3 Method 3: N-Methylenation .......................................... 256<br />

17.2.1.1.4.2.4 Method 4: Demethylation and Demethylenation ...................... 256<br />

17.2.1.1.4.2.5 Method 5: Oxidation to N-Oxides ..................................... 256<br />

17.2.1.1.4.2.6 Method 6: N-Amination .............................................. 257<br />

17.2.1.1.4.2.7 Method 7: Reduction <strong>of</strong> 1,2,3-Triazine N-Oxides ....................... 258<br />

17.2.1.1.4.2.8 Method 8: Diazotization <strong>of</strong> 2-Amino-4,6-dimethyl-1,2,3-triazinium ..... 258<br />

17.2.1.1.4.3 Modification <strong>of</strong> Substituents .............................................. 258<br />

17.2.1.1.4.3.1 Method 1: Oxidation <strong>of</strong> a-Hydroxy-Substituted Benzyl Groups ......... 258<br />

17.2.1.1.4.3.2 Method 2: Acylation <strong>of</strong> 4,6-Disubstituted 2-Amino-1,2,3-triaziniums ... 259<br />

17.2.1.2 Annulated 1,2,3-Triazines ................................................. 260<br />

17.2.1.2.1 Synthesis by Ring-Closure Reactions ....................................... 260<br />

17.2.1.2.1.1 By Annulation to a Heterocycle or Carbocycle .............................. 260<br />

17.2.1.2.1.1.1 By Formation <strong>of</strong> Two N—N Bonds .......................................... 260<br />

17.2.1.2.1.1.1.1 Method 1: Reaction <strong>of</strong> (2-Aminophenyl)arylimines with Nitrous Acid ... 260<br />

17.2.1.2.1.1.1.1.1 Variation 1: Reaction <strong>of</strong> 2-Aminoaryl Oximes with Nitrous Acid .......... 260<br />

17.2.1.2.1.1.1.2 Method 2: Reaction <strong>of</strong> 2-Aminobenzcarboxamides or<br />

Aminohetarenecarboxamides with Nitrous Acid ............ 261<br />

17.2.1.2.1.1.1.2.1 Variation 1: Reaction <strong>of</strong> 2-Aminoarenehydroxamic Acids and<br />

2-Aminoarenecarbohydrazides with Nitrous Acid ........... 265<br />

17.2.1.2.1.1.1.2.2 Variation 2: Reaction <strong>of</strong> 2-Aminothiobenzamides and Aminohetarenecarbothioamides<br />

with Nitrous Acid ......................... 266<br />

17.2.1.2.1.1.1.2.3 Variation 3: Reaction <strong>of</strong> 2-Aminobenzcarboxamidines and Related<br />

Compounds with Nitrous Acid ............................. 267<br />

17.2.1.2.1.1.1.2.4 Variation 4: Reaction <strong>of</strong> Aminohetarenecarbonitriles with Nitrous Acid<br />

and Hydrochloric Acid ..................................... 268<br />

17.2.1.2.1.1.1.3 Method 3: Cyclization <strong>of</strong> 2-Aminobenzonitriles and Related Compounds<br />

with Nitric Acid ........................................... 269<br />

17.2.1.2.1.1.1.4 Method 4: Diazotization <strong>of</strong> Naphthalene-1,8-diamines ................. 270<br />

17.2.1.2.1.1.1.4.1 Variation 1: Diazotization <strong>of</strong> (Aminohetaryl)azoles ...................... 271<br />

17.2.1.2.1.1.1.4.2 Variation 2: Diazotization <strong>of</strong> 2-(2-Aminophenyl)pyridines ............... 274

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