Detailed table of contents (pdf)

XXIV Table of Contents
17.2.1.2.4.1 Substitution of Existing Substituents ....................................... 298
17.2.1.2.4.1.1 Of Hydrogen .......................................................... 298
17.2.1.2.4.1.1.1 Method 1: Hydrogen–Deuterium Exchange ........................... 298
17.2.1.2.4.1.1.2 Method 2: Metalation ................................................ 298
17.2.1.2.4.1.1.3 Method 3: C-Halogenation ........................................... 298
17.2.1.2.4.1.1.4 Method 4: N-Acylation ............................................... 299
17.2.1.2.4.1.1.5 Method 5: N-Alkylation and N-Arylation .............................. 300
17.2.1.2.4.1.1.6 Method 6: N-Thiolation and N-Tosylation ............................. 303
17.2.1.2.4.1.1.7 Method 7: N-Amination .............................................. 303
17.2.1.2.4.1.2 Of Carbon Functionalities ................................................. 304
17.2.1.2.4.1.2.1 Method 1: N-Deacylation and N-Dealkylation ......................... 304
17.2.1.2.4.1.3 Of Heteroatoms .......................................................... 304
17.2.1.2.4.1.3.1 Method 1: Substitution of Halogen ................................... 304
17.2.1.2.4.1.3.1.1 Variation 1: Replacement of the 4-Chloro Substituent by Sulfur ......... 305
17.2.1.2.4.1.3.1.2 Variation 2: Replacement of the 4-Chloro Substituent by Amino
or Hydrazino Groups ...................................... 305
17.2.1.2.4.1.3.2 Method 2: Substitution of the 4-Oxo Group ........................... 305
17.2.1.2.4.1.3.2.1 Variation 1: Replacement of a 4-Oxo by a Thioxo Group ................. 306
17.2.1.2.4.1.3.2.2 Variation 2: Replacement of a 4-Oxo by Amino Groups .................. 307
17.2.1.2.4.1.3.3 Method 3: Substitution of the 4-Methoxy Group ...................... 307
17.2.1.2.4.1.3.4 Method 4: Substitution of the 4-Thioxo Group ........................ 308
17.2.1.2.4.1.3.5 Method 5: Substitution of the 4-(Methylsulfanyl) Group ............... 309
17.2.1.2.4.1.3.6 Method 6: Substitution of Amino, 4-Hydrazino, and
4-(1,2,4-Triazol-1-yl) Groups ............................... 310
17.2.1.2.4.2 Addition Reactions ....................................................... 310
17.2.1.2.4.2.1 Method 1: Alkylation of 4-(Arylamino)-1,2,3-benzotriazines ............ 310
17.2.1.2.4.2.2 Method 2: Oxidation to N-Oxides ..................................... 311
17.2.1.2.4.2.3 Method 3: Deoxygenation of N-Oxides ................................ 312
17.2.1.2.4.3 Rearrangement of Substituents ........................................... 313
17.2.1.2.4.3.1 Method 1: Photoisomerization of 2-Substituted
1,2,3-Benzotriazinium-4-olates ............................ 313
17.2.1.2.4.3.2 Method 2: Rearrangement of Annulated 3-Substituted
1,2,3-Triazin-4(3H)-imines ................................. 313
17.2.1.2.4.4 Modification of Substituents .............................................. 314
17.2.1.2.4.4.1 Method 1: Reactions of 2-Methyl Substituents of
Naphtho[1,8-d,e][1,2,3]triazine ............................ 314
17.2.1.2.4.4.2 Method 2: Reactions of Chloromethyl Substituents .................... 314
17.2.1.2.4.4.3 Method 3: Reactions of Hydroxyalkyl Substituents ..................... 314
17.2.1.2.4.4.4 Method 4: Modification of Oxygen Functionalities ..................... 315
17.2.1.2.4.4.5 Method 5: Modification of 4-Thioxo and 4-Methylsulfanyl Substituents . 315
17.2.1.2.4.4.6 Method 6: Modification of Nitrogen Functionalities .................... 316
17.2.1.3 Monocyclic 1,2,3l 5 -Diazaphosphinines ..................................... 317
17.2.1.3.1 Synthesis by Ring-Closure Reactions ....................................... 317