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XXXIV Table of Contents 17.2.3.1.1.2.2.12 Method 12: Reaction of [1-(Acylamino)-2-chlorovinyl]triphenylphosphonium Chlorides with Benzimidamides .............. 494 17.2.3.1.1.2.2.13 Method 13: Reaction of N-(2,2-Dicyanovinyl)thioimidates with Amidine Derivatives ............................................... 494 17.2.3.1.1.2.3 Fragments N—C—N—C—N and C ........................................... 495 17.2.3.1.1.2.3.1 Method 1: Reaction of N 2 -Cyanoamidine Derivatives with Chloromethaniminium Salts ..................................... 495 17.2.3.1.1.2.3.2 Method 2: Reaction of Biuret with Carboxylic Acid Derivatives .......... 497 17.2.3.1.1.2.3.3 Method 3: Reaction of Imidodicarbonimidates with C 1 Fragments ...... 498 17.2.3.1.1.2.3.4 Method 4: Reaction of 2-Alkylisourea-1-carboximidamide and Its Thio Analogues or Thiourea-1-carboximidamide with Carboxylic Acid Derivatives ........................................... 499 17.2.3.1.1.2.3.5 Method 5: Reaction of Sodium Dicyanamide or Guanidine-1-carbonitrile with Acid Derivatives ...................................... 500 17.2.3.1.1.2.3.6 Method 6: Reaction of Biguanides with Carboxylic Acid Derivatives ..... 500 17.2.3.1.1.2.3.7 Method 7: Reaction of 1-Carboximidoylguanidines with Carboxylic Acid Derivatives ........................................... 502 17.2.3.1.1.2.4 Fragments C—N—C—N—C and N ........................................... 503 17.2.3.1.1.2.4.1 Method 1: Reaction of N 1 ,N 2 -Dicyanoamidines with Hydroxylamine ..... 503 17.2.3.1.1.3 By Formation of One N—C Bond ........................................... 503 17.2.3.1.1.3.1 Fragment N—C—N—C—N—C ............................................... 503 17.2.3.1.1.3.1.1 Method 1: Cyclization of Guanidine-1,2-dicarbonitriles and Their Salts .. 503 17.2.3.1.1.3.1.1.1 Variation 1: With Hydrogen Halides .................................... 503 17.2.3.1.1.3.1.1.2 Variation 2: With Hydrogen Sulfide .................................... 504 17.2.3.1.1.3.1.1.3 Variation 3: With Amines .............................................. 505 17.2.3.1.1.3.1.2 Method 2: Cyclization of 3-Acylguanidine-1-carbonitriles .............. 505 17.2.3.1.1.3.1.3 Method 3: Cyclization of N 1 ,N 2 -Diacylamidine Derivatives .............. 506 17.2.3.1.1.3.1.4 Method 4: Cyclization of 1,3,5-Triazahexa-1,4-dienylium Perchlorates .. 508 17.2.3.1.2 Synthesis by Ring Transformation .......................................... 508 17.2.3.1.2.1 By Ring Enlargement ..................................................... 508 17.2.3.1.2.1.1 Method 1: From 2-(Cyanoimino)thiazolidines and Amines ............. 508 17.2.3.1.2.1.2 Method 2: From Imidazoles .......................................... 509 17.2.3.1.2.1.3 Method 3: Thermolysis of 3-Phenyl-1,2,4-oxadiazol-5-amines .......... 510 17.2.3.1.2.1.4 Method 4: Electroreduction of 3,4-Diphenyl-1,2,5-thiadiazole 1-Oxide .. 511 17.2.3.1.2.2 Formal Exchange of Ring Members with Retention of the Ring Size .......... 511 17.2.3.1.2.2.1 Method 1: Reaction of 4H-1,3-Benzoxazin-4-ones with Amidine Derivatives ............................................... 511 17.2.3.1.2.2.2 Method 2: Rearrangement of Pyrimidine Derivatives ................... 512 17.2.3.1.2.2.2.1 Variation 1: Conversion of 5-Nitrosopyrimidin-4-amines into 1,3,5-Triazine-2-carbonitriles .............................. 513 17.2.3.1.2.2.2.2 Variation 2: Reaction of 4-Chloropyrimidines with Potassium Amide ..... 513 17.2.3.1.2.2.2.3 Variation 3: Oxidation of Pyrimidinediamines ........................... 514 17.2.3.1.2.2.3 Method 3: Conversion of 1,3,5-Oxadiazines and Their Salts into 1,3,5-Triazines ............................................ 515
Table of Contents XXXV 17.2.3.1.2.2.4 Method 4: Conversion of 1,2,4-Triazines into 1,3,5-Triazines ............ 516 17.2.3.1.2.2.5 Method 5: Conversion of 1,2,3,5-Oxathiadiazine 2,2-Dioxides into 1,3,5-Triazines ............................................ 517 17.2.3.1.2.2.6 Method 6: Conversion of 1,2,3,5-Tetrazines into 1,3,5-Triazines ........ 518 17.2.3.1.2.2.7 Method 7: Conversion of 1,3,5,2l 5 ,4l 5 ,6l 5 -Triazatriphosphinines into 1,3,5-Triazines ............................................ 519 17.2.3.1.3 Aromatization ............................................................ 519 17.2.3.1.3.1 By Oxidation .............................................................. 519 17.2.3.1.3.1.1 Method 1: By Dehydrogenation of Dihydro-1,3,5-triazines ............. 519 17.2.3.1.3.1.2 Method 2: By Dehydrogenation of 2,4,6-Triaryl-1,2-dihydro-1,3,5triazines with Sulfite ...................................... 520 17.2.3.1.3.2 By Elimination ............................................................ 521 17.2.3.1.3.2.1 Method 1: Haloform Reaction ........................................ 521 17.2.3.1.4 Synthesis by Substituent Modification ..................................... 522 17.2.3.1.4.1 Substitution of Existing Substituents ....................................... 522 17.2.3.1.4.1.1 Of Hydrogen .............................................................. 522 17.2.3.1.4.1.1.1 Method 1: Cyanation ................................................ 522 17.2.3.1.4.1.1.2 Method 2: C-Alkylation .............................................. 522 17.2.3.1.4.1.1.2.1 Variation 1: Reaction of 2,4-Diphenyl-1,3,5-triazine with Active Methylene Compounds .............................................. 522 17.2.3.1.4.1.1.2.2 Variation 2: Reaction of 1,3,5-Triazine with Amidines and Imidates ...... 522 17.2.3.1.4.1.1.2.3 Variation 3: Dimroth Rearrangements ................................. 523 17.2.3.1.4.1.1.3 Method 3: Halogenation ............................................. 524 17.2.3.1.4.1.1.4 Method 4: Amination ................................................ 525 17.2.3.1.4.1.2 Of Metals ................................................................ 525 17.2.3.1.4.1.2.1 Method 1: Reaction of 1,3,5-Triazinyllithium with Ketones ............. 525 17.2.3.1.4.1.3 Of Carbon Functionalities ................................................. 525 17.2.3.1.4.1.3.1 Method 1: Decarboxylation .......................................... 525 17.2.3.1.4.1.3.2 Method 2: Substitution of Trichloromethyl Groups .................... 525 17.2.3.1.4.1.3.3 Method 3: Substitution of Trinitromethyl Groups ...................... 526 17.2.3.1.4.1.4 Of Heteroatoms .......................................................... 527 17.2.3.1.4.1.4.1 Dehalogenation .......................................................... 527 17.2.3.1.4.1.4.1.1 Method 1: Reductive Dechlorination .................................. 527 17.2.3.1.4.1.4.2 Substitution of Halogens by Carbon Functionalities ......................... 528 17.2.3.1.4.1.4.2.1 Method 1: Reaction with Organolithium Reagents ..................... 528 17.2.3.1.4.1.4.2.2 Method 2: Reaction with Grignard Reagents .......................... 529 17.2.3.1.4.1.4.2.3 Method 3: Reaction with Arylboronic Acids (Suzuki Coupling) .......... 530 17.2.3.1.4.1.4.2.4 Method 4: Reaction with Perfluoroalkylsilanes ......................... 530 17.2.3.1.4.1.4.2.5 Method 5: Reaction with Organotin Reagents ......................... 531 17.2.3.1.4.1.4.2.6 Method 6: Friedel–Crafts Reactions ................................... 532 17.2.3.1.4.1.4.2.7 Method 7: Reaction with Active Methylene Compounds ............... 533 17.2.3.1.4.1.4.2.8 Method 8: Reaction with Cyanide ..................................... 535
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 and 10: Table of Contents XVII 17.1.3.2 1,4
Page 11 and 12: Table of Contents XIX 17.1.3.3.1.1.
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: Table of Contents XXXIII 17.2.3.1.1
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
Page 61: Table of Contents LXIX 17.9.22.3 Me

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