Detailed table of contents (pdf)
Detailed table of contents (pdf) Detailed table of contents (pdf)
XVIII Table of Contents 17.1.3.2.3.1.1.2.2 Variation 2: Alkenylation and Alkylation ................................ 149 17.1.3.2.3.1.1.3 Method 3: By Halogens .............................................. 152 17.1.3.2.3.1.1.3.1 Variation 1: Direct Halogenation ....................................... 152 17.1.3.2.3.1.2 Of Halogens .............................................................. 152 17.1.3.2.3.1.2.1 Method 1: By Nucleophiles ........................................... 152 17.1.3.2.3.1.3 Of Oxygen ............................................................... 153 17.1.3.2.3.1.3.1 Method 1: By Hydrogen .............................................. 153 17.1.3.2.3.1.4 Of Nitrogen .............................................................. 153 17.1.3.2.3.1.4.1 Method 1: Deacylation ............................................... 153 17.1.3.2.3.1.4.2 Method 2: Dealkylation .............................................. 153 17.1.3.2.3.2 Addition Reactions ....................................................... 154 17.1.3.2.3.2.1 Of Hydrogen ............................................................. 154 17.1.3.2.3.2.1.1 Method 1: By Reduction of 1,4-Benzothiazines ........................ 154 17.1.3.2.3.2.1.2 Method 2: By Oxidation at Sulfur ..................................... 155 17.1.3.2.3.3 Rearrangement of Substituents ........................................... 157 17.1.3.2.3.3.1 Method 1: Of an Acetoxy Group ...................................... 157 17.1.3.2.3.3.2 Method 2: Of an Alkoxycarbonyl Group ............................... 157 17.1.3.2.3.3.3 Method 3: Of a Methyl Group ........................................ 158 17.1.3.2.3.3.4 Method 4: Of an Allyl Group .......................................... 158 17.1.3.2.3.3.5 Method 5: Configurational Isomerization ............................. 158 17.1.3.2.3.4 Modification of Substituents .............................................. 159 17.1.3.2.3.4.1 Method 1: By Aldolization ............................................ 159 17.1.3.2.3.4.2 Method 2: By Lithiation and Electrophilic Attack ....................... 159 17.1.3.3 Phenothiazines .......................................................... 160 17.1.3.3.1 Synthesis by Ring-Closure Reactions ....................................... 163 17.1.3.3.1.1 Annulation to an Arene or a Hetarene ..................................... 163 17.1.3.3.1.1.1 By Formation of Two S—C Bonds ........................................... 163 17.1.3.3.1.1.1.1 Method 1: From S-[2-Amino-5-(dimethylamino)phenyl] Hydrogen Thiosulfate and N,N-Dimethylaniline ....................... 163 17.1.3.3.1.1.1.2 Method 2: From Arylamines and Sulfur ............................... 164 17.1.3.3.1.1.1.2.1 Variation 1: From Diarylamines and Sulfur .............................. 164 17.1.3.3.1.1.1.2.2 Variation 2: From Oligomeric Diphenylamines and Related Compounds .. 168 17.1.3.3.1.1.1.2.3 Variation 3: From Hetarylamines ...................................... 170 17.1.3.3.1.1.1.2.4 Variation 4: From Diarylamines and Sulfuryl Chloride, Thionyl Chloride, or Sulfur Dichloride ....................................... 171 17.1.3.3.1.1.1.2.5 Variation 5: From (Arylamino)-1,4-quinones and Sodium Sulfide ......... 172 17.1.3.3.1.1.2 By Formation of One S—C and One N—C Bond .............................. 172 17.1.3.3.1.1.2.1 Method 1: From Arylamines and 1-(Anilinosulfanyl)-2-nitrobenzenes ... 172 17.1.3.3.1.1.2.2 Method 2: From Aminoarenethiols ................................... 173 17.1.3.3.1.1.2.2.1 Variation 1: From 2-Aminoarenethiols and Quinones ................... 173 17.1.3.3.1.1.2.2.2 Variation 2: From Heterocyclic Quinones ............................... 175
Table of Contents XIX 17.1.3.3.1.1.2.2.3 Variation 3: From 4,8-Bis(alkylamino)naphtho-1,5-quinones ............. 177 17.1.3.3.1.1.2.2.4 Variation 4: From 1,3-Diketones and Related Compounds ............... 177 17.1.3.3.1.1.2.2.5 Variation 5: From Polycyclic Quinones ................................. 178 17.1.3.3.1.1.2.3 Method 3: From Zinc Aminoarenethiolates and Haloquinones .......... 178 17.1.3.3.1.1.2.3.1 Variation 1: From Chlorohydroquinones ................................ 178 17.1.3.3.1.1.2.3.2 Variation 2: From Haloquinones ....................................... 179 17.1.3.3.1.1.3 By Formation of One N—C Bond ........................................... 183 17.1.3.3.1.1.3.1 Method 1: From Diaryl Sulfides and Related Compounds ............... 183 17.1.3.3.1.1.3.1.1 Variation 1: From 2-Azidophenyl Phenyl Sulfides ........................ 183 17.1.3.3.1.1.3.1.2 Variation 2: From 2-Nitrophenyl Phenyl Sulfides ........................ 184 17.1.3.3.1.1.3.1.3 Variation 3: From 2-Aminophenyl 2-Nitrophenyl Sulfides or 2-(Acylamino)phenyl 2-Nitrophenyl Sulfides ................ 185 17.1.3.3.1.1.3.1.4 Variation 4: From 2-Aminophenyl 2-Nitrophenyl Sulfides via 2-Aminobenzenethiol and Halodinitrobenzenes ............ 187 17.1.3.3.1.1.3.1.5 Variation 5: From 2-Aminophenyl 2-Halophenyl Sulfides ................ 189 17.1.3.3.1.1.3.1.6 Variation 6: From 2-Aminophenyl and 2-Aminohetaryl 2-Halodiazinyl Sulfides ................................................... 192 17.1.3.3.1.1.3.1.7 Variation 7: From 5-[(2-Aminoaryl)sulfanyl]pyrimidin-4-ol, or from 6-[(2-Acetylaminophenyl)sulfanyl]-1,3-dimethyluracil ....... 195 17.1.3.3.1.1.4 Miscellaneous Ring-Closure Reactions ..................................... 196 17.1.3.3.1.1.4.1 Method 1: By Thermolysis of 1,2,4-Triazines ........................... 196 17.1.3.3.2 Synthesis by Ring Transformation .......................................... 197 17.1.3.3.2.1 By Ring Enlargement ..................................................... 197 17.1.3.3.2.1.1 Method 1: Of 2,3-Dihydrobenzothiazoles with N-Bromosuccinimide .... 197 17.1.3.3.2.1.2 Method 2: Of 2,3-Dihydrobenzothiazoles with Sulfuryl Chloride ........ 197 17.1.3.3.2.1.3 Method 3: Of 1,2,3-Benzothiadiazole ................................. 198 17.1.3.3.2.2 Formal Exchange of Ring Members with Retention of the Ring Size .......... 198 17.1.3.3.2.2.1 Method 1: From 10-Chloro-5,10-dihydrophenarsenazine and Sulfuryl Chloride .................................................. 198 17.1.3.3.2.3 By Ring Contraction ...................................................... 198 17.1.3.3.2.3.1 Method 1: Of Pyrimido[1,5]benzothiazepines ......................... 198 17.1.3.3.3 Synthesis by Substituent Modification ..................................... 199 17.1.3.3.3.1 Substitution of Existing Substituents ....................................... 199 17.1.3.3.3.1.1 Of Hydrogen ............................................................. 199 17.1.3.3.3.1.1.1 Method 1: By Metals ................................................. 199 17.1.3.3.3.1.1.2 Method 2: By Acylation or Alkylation ................................. 200 17.1.3.3.3.1.1.3 Method 3: By Halogenation .......................................... 201 17.1.3.3.3.1.1.4 Method 4: By Nitration ............................................... 202 17.1.3.3.3.1.2 Of Halogen ............................................................... 202 17.1.3.3.3.1.2.1 Method 1: By Metals ................................................. 202 17.1.3.3.3.1.2.2 Method 2: By Hydrogen .............................................. 203 17.1.3.3.3.2 Addition Reactions ....................................................... 203
- Page 1 and 2: Table of Contents IX Volume 17: Six
- Page 3 and 4: Table of Contents XI Table of Conte
- Page 5 and 6: Table of Contents XIII 17.1.1.2.4.1
- Page 7 and 8: Table of Contents XV 17.1.2.3.1.3 B
- Page 9: Table of Contents XVII 17.1.3.2 1,4
- Page 13 and 14: Table of Contents XXI 17.2 Product
- Page 15 and 16: Table of Contents XXIII 17.2.1.2.1.
- Page 17 and 18: Table of Contents XXV 17.2.1.3.1.1
- Page 19 and 20: Table of Contents XXVII 17.2.2 Prod
- Page 21 and 22: Table of Contents XXIX 17.2.2.1.3.3
- Page 23 and 24: Table of Contents XXXI 17.2.2.2.1.4
- Page 25 and 26: Table of Contents XXXIII 17.2.3.1.1
- Page 27 and 28: Table of Contents XXXV 17.2.3.1.2.2
- Page 29 and 30: Table of Contents XXXVII 17.2.3.1.4
- Page 31 and 32: Table of Contents XXXIX 17.3.3.2 Sy
- Page 33 and 34: Table of Contents XLI 17.4.2.2.2.2
- Page 35 and 36: Table of Contents XLIII 17.4.4.1.2.
- Page 37 and 38: Table of Contents XLV 17.4.5.1.2.3
- Page 39 and 40: Table of Contents XLVII 17.4.5.4.1.
- Page 41 and 42: Table of Contents XLIX 17.4.6.2.4.2
- Page 43 and 44: Table of Contents LI 17.4.6.5.4.2 A
- Page 45 and 46: Table of Contents LIII 17.4.6.7.4.4
- Page 47 and 48: Table of Contents LV 17.5.2.2.1 Met
- Page 49 and 50: Table of Contents LVII 17.6.2.1.1.4
- Page 51 and 52: Table of Contents LIX 17.6.5.2.2.1.
- Page 53 and 54: Table of Contents LXI 17.7.3.2 [2.3
- Page 55 and 56: Table of Contents LXIII 17.7.5.1.2.
- Page 57 and 58: Table of Contents LXV 17.8.3.2 Cont
- Page 59 and 60: Table of Contents LXVII 17.9.8.3 Me
XVIII Table <strong>of</strong> Contents<br />
17.1.3.2.3.1.1.2.2 Variation 2: Alkenylation and Alkylation ................................ 149<br />
17.1.3.2.3.1.1.3 Method 3: By Halogens .............................................. 152<br />
17.1.3.2.3.1.1.3.1 Variation 1: Direct Halogenation ....................................... 152<br />
17.1.3.2.3.1.2 Of Halogens .............................................................. 152<br />
17.1.3.2.3.1.2.1 Method 1: By Nucleophiles ........................................... 152<br />
17.1.3.2.3.1.3 Of Oxygen ............................................................... 153<br />
17.1.3.2.3.1.3.1 Method 1: By Hydrogen .............................................. 153<br />
17.1.3.2.3.1.4 Of Nitrogen .............................................................. 153<br />
17.1.3.2.3.1.4.1 Method 1: Deacylation ............................................... 153<br />
17.1.3.2.3.1.4.2 Method 2: Dealkylation .............................................. 153<br />
17.1.3.2.3.2 Addition Reactions ....................................................... 154<br />
17.1.3.2.3.2.1 Of Hydrogen ............................................................. 154<br />
17.1.3.2.3.2.1.1 Method 1: By Reduction <strong>of</strong> 1,4-Benzothiazines ........................ 154<br />
17.1.3.2.3.2.1.2 Method 2: By Oxidation at Sulfur ..................................... 155<br />
17.1.3.2.3.3 Rearrangement <strong>of</strong> Substituents ........................................... 157<br />
17.1.3.2.3.3.1 Method 1: Of an Acetoxy Group ...................................... 157<br />
17.1.3.2.3.3.2 Method 2: Of an Alkoxycarbonyl Group ............................... 157<br />
17.1.3.2.3.3.3 Method 3: Of a Methyl Group ........................................ 158<br />
17.1.3.2.3.3.4 Method 4: Of an Allyl Group .......................................... 158<br />
17.1.3.2.3.3.5 Method 5: Configurational Isomerization ............................. 158<br />
17.1.3.2.3.4 Modification <strong>of</strong> Substituents .............................................. 159<br />
17.1.3.2.3.4.1 Method 1: By Aldolization ............................................ 159<br />
17.1.3.2.3.4.2 Method 2: By Lithiation and Electrophilic Attack ....................... 159<br />
17.1.3.3 Phenothiazines .......................................................... 160<br />
17.1.3.3.1 Synthesis by Ring-Closure Reactions ....................................... 163<br />
17.1.3.3.1.1 Annulation to an Arene or a Hetarene ..................................... 163<br />
17.1.3.3.1.1.1 By Formation <strong>of</strong> Two S—C Bonds ........................................... 163<br />
17.1.3.3.1.1.1.1 Method 1: From S-[2-Amino-5-(dimethylamino)phenyl] Hydrogen<br />
Thiosulfate and N,N-Dimethylaniline ....................... 163<br />
17.1.3.3.1.1.1.2 Method 2: From Arylamines and Sulfur ............................... 164<br />
17.1.3.3.1.1.1.2.1 Variation 1: From Diarylamines and Sulfur .............................. 164<br />
17.1.3.3.1.1.1.2.2 Variation 2: From Oligomeric Diphenylamines and Related Compounds .. 168<br />
17.1.3.3.1.1.1.2.3 Variation 3: From Hetarylamines ...................................... 170<br />
17.1.3.3.1.1.1.2.4 Variation 4: From Diarylamines and Sulfuryl Chloride, Thionyl Chloride,<br />
or Sulfur Dichloride ....................................... 171<br />
17.1.3.3.1.1.1.2.5 Variation 5: From (Arylamino)-1,4-quinones and Sodium Sulfide ......... 172<br />
17.1.3.3.1.1.2 By Formation <strong>of</strong> One S—C and One N—C Bond .............................. 172<br />
17.1.3.3.1.1.2.1 Method 1: From Arylamines and 1-(Anilinosulfanyl)-2-nitrobenzenes ... 172<br />
17.1.3.3.1.1.2.2 Method 2: From Aminoarenethiols ................................... 173<br />
17.1.3.3.1.1.2.2.1 Variation 1: From 2-Aminoarenethiols and Quinones ................... 173<br />
17.1.3.3.1.1.2.2.2 Variation 2: From Heterocyclic Quinones ............................... 175
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