Detailed table of contents (pdf)
Detailed table of contents (pdf) Detailed table of contents (pdf)
XIV Table of Contents 17.1.2.2.1.2 By Formation of One O—C Bond ............................................ 65 17.1.2.2.1.2.1 Method 1: From 6,7,8-Trifluoroquinoline-1-acetaldehydes .............. 66 17.1.2.2.1.2.2 Method 2: By Ring Closure of N-Substituted 2-Aminophenols ........... 66 17.1.2.2.1.3 By Formation of One N—C Bond ............................................ 67 17.1.2.2.1.3.1 Method 1: By Ring Closure of O-Substituted 2-Aminophenols ........... 67 17.1.2.2.1.3.2 Method 2: Reductive Cyclization of 2-Nitrophenols ..................... 69 17.1.2.2.2 Synthesis by Ring Transformation ........................................... 72 17.1.2.2.2.1 Method 1: By Ring Enlargement ....................................... 72 17.1.2.2.2.2 Method 2: Heterocyclic Ring Size Retained ............................. 73 17.1.2.2.3 Aromatization ............................................................. 73 17.1.2.2.3.1 Method 1: By Dehydrogenation ....................................... 73 17.1.2.2.3.1.1 Variation 1: By Oxidation of Dihydro-1,4-benzoxazines ................... 74 17.1.2.2.3.1.2 Variation 2: By Aromatization of 1,4-Benzoxazin-3-ones .................. 74 17.1.2.2.3.2 Method 2: By Elimination ............................................. 75 17.1.2.2.4 Synthesis by Substituent Modification ...................................... 75 17.1.2.2.4.1 Substitution of Existing Substituents ........................................ 75 17.1.2.2.4.1.1 Of Hydrogen .............................................................. 75 17.1.2.2.4.1.1.1 Method 1: By Alkylation or Acetylation ................................ 75 17.1.2.2.4.1.1.2 Method 2: By Bromine ................................................ 76 17.1.2.2.4.1.1.3 Method 3: By Oxygen ................................................. 76 17.1.2.2.4.2 Synthesis by Reduction of 1,4-Benzoxazines ................................. 77 17.1.2.2.4.2.1 Method 1: By Hydrogenation .......................................... 77 17.1.2.2.4.2.2 Method 2: By Electrochemical and Chemical Reduction ................. 77 17.1.2.3 Phenoxazines .............................................................. 78 17.1.2.3.1 Synthesis by Ring-Closure Reactions ........................................ 79 17.1.2.3.1.1 By Formation of One O—C and Two N—C Bonds ............................. 80 17.1.2.3.1.1.1 Method 1: From Nitrosoarenes and 2,5-Dihydroxybenzo-1,4-quinones ... 80 17.1.2.3.1.1.2 Method 2: Nitration of 3-Methoxyphenol .............................. 80 17.1.2.3.1.2 By Formation of One O—C and One N—C Bond .............................. 80 17.1.2.3.1.2.1 Method 1: From 2-Aminophenols ...................................... 80 17.1.2.3.1.2.1.1 Variation 1: By Oxidation ............................................... 81 17.1.2.3.1.2.1.2 Variation 2: By Self-Condensation ....................................... 82 17.1.2.3.1.2.1.3 Variation 3: By Reactions with 2-Chloronitrobenzenes ................... 82 17.1.2.3.1.2.1.4 Variation 4: By Reactions with Pyrocatechol ............................. 84 17.1.2.3.1.2.1.5 Variation 5: By Reactions with 2-Hydroxy- or 2-Halobenzo-1,4-quinones .. 85 17.1.2.3.1.2.1.6 Variation 6: By Reactions with Indazole-4,7-diones ...................... 92 17.1.2.3.1.2.1.7 Variation 7: By Reactions with Dimethyl 2-Amino-3-oxophenoxazine-1,9dicarboxylate .............................................. 92 17.1.2.3.1.2.2 Method 2: From Phenols and 1-Nitroso-2-naphthol ..................... 93 17.1.2.3.1.2.3 Method 3: From N-Chlorobenzoquinone Imines and Phenols ............ 94 17.1.2.3.1.2.4 Method 4: From Nitrosoanilines and Phenols ........................... 95
Table of Contents XV 17.1.2.3.1.3 By Formation of One O—C Bond ............................................ 96 17.1.2.3.1.3.1 Method 1: From (2-Hydroxyaryl)(2-nitroaryl)amines .................... 96 17.1.2.3.1.3.2 Method 2: From Bis(2-alkoxyaryl)amines ............................... 96 17.1.2.3.1.3.3 Method 3: From 2,5-Dianilinobenzo-1,4-quinones ...................... 97 17.1.2.3.1.4 By Formation of One N—C Bond ............................................ 99 17.1.2.3.1.4.1 Method 1: From Diaryl Ethers ......................................... 99 17.1.2.3.1.4.1.1 Variation 1: By Cyclization of 2-Aminoaryl 2-Haloaryl Ethers .............. 99 17.1.2.3.1.4.1.2 Variation 2: By Cyclization of 2-Aminoaryl 2-Nitroaryl Ethers ............ 101 17.1.2.3.1.4.1.3 Variation 3: By Cyclization of 2-Aminoaryl or 2-Nitroaryl Aryl Ethers ..... 101 17.1.2.3.2 Synthesis by Substituent Modification ..................................... 102 17.1.2.3.2.1 Substitution of Existing Substituents ....................................... 102 17.1.2.3.2.1.1 Of Hydrogen ............................................................. 102 17.1.2.3.2.1.1.1 Method 1: By Metalation ............................................. 102 17.1.2.3.2.1.1.2 Method 2: By Friedel–Crafts Acylation, Halogenation, or Nitration ...... 103 17.1.2.3.2.1.1.3 Method 3: By Oxidative Substitution .................................. 104 17.1.2.3.2.1.2 Of Alkyl Groups .......................................................... 105 17.1.2.3.2.1.2.1 Method 1: Demethylation ............................................ 105 17.1.2.3.2.1.3 Of Halogen ............................................................... 105 17.1.2.3.2.1.3.1 Method 1: Reductive Dehalogenation ................................. 105 17.1.2.3.2.2 Modification of Substituents .............................................. 105 17.1.2.3.2.2.1 Method 1: Reductive O-Methylation of Phenoxazin-3-one .............. 105 17.1.2.4 1,4-Oxaphosphinines and Phenoxaphosphines ............................. 106 17.1.2.4.1 Synthesis by Ring-Closure Reactions ....................................... 106 17.1.2.4.1.1 By Formation of Two O—C Bonds .......................................... 106 17.1.2.4.1.1.1 Method 1: From Phosphorylethenamines ............................. 106 17.1.2.4.1.1.2 Method 2: From Bis(2-oxo-2-phenylethyl)phosphinic acid .............. 106 17.1.2.4.1.2 By Formation of One O—C and One P—C Bond ............................. 107 17.1.2.4.1.2.1 Method 1: From Alkynylphosphines and Bromo Ketones ............... 107 17.1.2.4.1.2.2 Method 2: From 1-Phenyl-2-(triphenylphosphonio)ethenolate ......... 107 17.1.2.4.1.3 By Formation of Two P—C Bonds ........................................... 108 17.1.2.4.1.3.1 Method 1: From Diaryl Ethers ........................................ 108 17.1.2.4.1.3.1.1 Variation 1: From Bis(2-lithiophenyl) Ether ............................. 108 17.1.2.4.1.3.1.2 Variation 2: With Phosphorus Chlorides and Aluminum Trichloride ....... 108 17.1.2.4.1.3.1.3 Variation 3: From Diaryl Ether 2-Diazonium Salts ....................... 109 17.1.2.4.2 Synthesis by Substituent Modification ..................................... 110 17.1.2.4.2.1 Substitution of Existing Substituents ....................................... 110 17.1.2.4.2.1.1 Of Heteroatoms .......................................................... 110 17.1.2.4.2.1.1.1 Method 1: By Reduction of 4-Substituted Oxaphosphinines 4-Oxides ... 110
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- Page 29 and 30: Table of Contents XXXVII 17.2.3.1.4
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XIV Table <strong>of</strong> Contents<br />
17.1.2.2.1.2 By Formation <strong>of</strong> One O—C Bond ............................................ 65<br />
17.1.2.2.1.2.1 Method 1: From 6,7,8-Trifluoroquinoline-1-acetaldehydes .............. 66<br />
17.1.2.2.1.2.2 Method 2: By Ring Closure <strong>of</strong> N-Substituted 2-Aminophenols ........... 66<br />
17.1.2.2.1.3 By Formation <strong>of</strong> One N—C Bond ............................................ 67<br />
17.1.2.2.1.3.1 Method 1: By Ring Closure <strong>of</strong> O-Substituted 2-Aminophenols ........... 67<br />
17.1.2.2.1.3.2 Method 2: Reductive Cyclization <strong>of</strong> 2-Nitrophenols ..................... 69<br />
17.1.2.2.2 Synthesis by Ring Transformation ........................................... 72<br />
17.1.2.2.2.1 Method 1: By Ring Enlargement ....................................... 72<br />
17.1.2.2.2.2 Method 2: Heterocyclic Ring Size Retained ............................. 73<br />
17.1.2.2.3 Aromatization ............................................................. 73<br />
17.1.2.2.3.1 Method 1: By Dehydrogenation ....................................... 73<br />
17.1.2.2.3.1.1 Variation 1: By Oxidation <strong>of</strong> Dihydro-1,4-benzoxazines ................... 74<br />
17.1.2.2.3.1.2 Variation 2: By Aromatization <strong>of</strong> 1,4-Benzoxazin-3-ones .................. 74<br />
17.1.2.2.3.2 Method 2: By Elimination ............................................. 75<br />
17.1.2.2.4 Synthesis by Substituent Modification ...................................... 75<br />
17.1.2.2.4.1 Substitution <strong>of</strong> Existing Substituents ........................................ 75<br />
17.1.2.2.4.1.1 Of Hydrogen .............................................................. 75<br />
17.1.2.2.4.1.1.1 Method 1: By Alkylation or Acetylation ................................ 75<br />
17.1.2.2.4.1.1.2 Method 2: By Bromine ................................................ 76<br />
17.1.2.2.4.1.1.3 Method 3: By Oxygen ................................................. 76<br />
17.1.2.2.4.2 Synthesis by Reduction <strong>of</strong> 1,4-Benzoxazines ................................. 77<br />
17.1.2.2.4.2.1 Method 1: By Hydrogenation .......................................... 77<br />
17.1.2.2.4.2.2 Method 2: By Electrochemical and Chemical Reduction ................. 77<br />
17.1.2.3 Phenoxazines .............................................................. 78<br />
17.1.2.3.1 Synthesis by Ring-Closure Reactions ........................................ 79<br />
17.1.2.3.1.1 By Formation <strong>of</strong> One O—C and Two N—C Bonds ............................. 80<br />
17.1.2.3.1.1.1 Method 1: From Nitrosoarenes and 2,5-Dihydroxybenzo-1,4-quinones ... 80<br />
17.1.2.3.1.1.2 Method 2: Nitration <strong>of</strong> 3-Methoxyphenol .............................. 80<br />
17.1.2.3.1.2 By Formation <strong>of</strong> One O—C and One N—C Bond .............................. 80<br />
17.1.2.3.1.2.1 Method 1: From 2-Aminophenols ...................................... 80<br />
17.1.2.3.1.2.1.1 Variation 1: By Oxidation ............................................... 81<br />
17.1.2.3.1.2.1.2 Variation 2: By Self-Condensation ....................................... 82<br />
17.1.2.3.1.2.1.3 Variation 3: By Reactions with 2-Chloronitrobenzenes ................... 82<br />
17.1.2.3.1.2.1.4 Variation 4: By Reactions with Pyrocatechol ............................. 84<br />
17.1.2.3.1.2.1.5 Variation 5: By Reactions with 2-Hydroxy- or 2-Halobenzo-1,4-quinones .. 85<br />
17.1.2.3.1.2.1.6 Variation 6: By Reactions with Indazole-4,7-diones ...................... 92<br />
17.1.2.3.1.2.1.7 Variation 7: By Reactions with Dimethyl 2-Amino-3-oxophenoxazine-1,9dicarboxylate<br />
.............................................. 92<br />
17.1.2.3.1.2.2 Method 2: From Phenols and 1-Nitroso-2-naphthol ..................... 93<br />
17.1.2.3.1.2.3 Method 3: From N-Chlorobenzoquinone Imines and Phenols ............ 94<br />
17.1.2.3.1.2.4 Method 4: From Nitrosoanilines and Phenols ........................... 95