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XXVI Table of Contents 17.2.1.6.1.1.1.1 Method 1: Cyclization of Aminohetarenecarboxamides, Aminohetarenecarbothioamides, 2-Aminobenzamides, and Related Compounds with Phosphorus(V) Reagents ..... 330 17.2.1.6.1.1.1.1.1 Variation 1: Cyclization of Aminohetarenecarbonitriles with Lawesson s Reagent ....................................... 331 17.2.1.6.1.1.1.2 Method 2: Cyclization of 2-Aminobenzamides with Phosphorus Trichloride ................................................ 332 17.2.1.6.1.1.1.2.1 Variation 1: Cyclization of 2-[(w-Hydroxyalkyl)amino]benzamides with Tris(diethylamino)phosphine ............................... 334 17.2.1.6.1.1.1.3 Method 3: Cyclization of Naphthalene-1,8-diamine with Phosphorus(V) Dichlorides ................................. 334 17.2.1.6.1.1.2 By Formation of One N—P Bond ........................................... 335 17.2.1.6.1.1.2.1 Method 1: Cyclization of N-(2-Cyanophenyl)phosphinimidic Acid Chlorides ............................................ 335 17.2.1.6.1.1.3 By Formation of One N—C Bond ........................................... 336 17.2.1.6.1.1.3.1 Method 1: Cyclization of N-(Trimethylsilyl)-N-(phosphoranyl)benzamides 336 17.2.1.6.1.2 By Annulation to the 1,3,2l 5 -Diazaphosphinine Ring ........................ 337 17.2.1.6.1.2.1 Method 1: Cyclization of 1- or 3-(w-Haloalkyl)-1,3,2l 5 -benzodiazaphosphinines ........................................ 337 17.2.1.6.1.2.2 Method 2: Cyclization of 4-Chloro-1,3,2l 5 -diazaphosphinine-5-carbonitriles with Hydrazines ........................................... 338 17.2.1.6.2 Synthesis by Substituent Modification ..................................... 338 17.2.1.6.2.1 Substitution of Existing Substituents ....................................... 338 17.2.1.6.2.1.1 Of Hydrogen .............................................................. 338 17.2.1.6.2.1.1.1 Method 1: Substitution at Phosphorus with Carbon Functional Groups .. 338 17.2.1.6.2.1.2 Of Heteroatoms .......................................................... 339 17.2.1.6.2.1.2.1 Method 1: Replacement of Chloro Substituents by Amino Groups ...... 339 17.2.1.6.2.1.2.2 Method 2: Replacement of Alkylsulfanyl Substituents by Alkyl, Alkoxy, or Amino Groups .......................................... 340 17.2.1.6.2.2 Modification of Substituents .............................................. 340 17.2.1.6.2.2.1 Method 1: Alkylation of Sulfanyl and Thioxo Groups ................... 340 17.2.1.7 Monocyclic 1,2l 5 ,6l 5 -Azadiphosphinines .................................. 341 17.2.1.7.1 Synthesis by Ring-Closure Reactions ....................................... 341 17.2.1.7.1.1 By Formation of Two P—C Bonds ........................................... 341 17.2.1.7.1.1.1 Method 1: Cyclization of Propenes with Diphosphazanes .............. 341 17.2.1.8 Monocyclic 1l 5 ,2,3l 5 -Triphosphinines ..................................... 343 17.2.1.8.1 Synthesis by Ring-Closure Reactions ....................................... 343 17.2.1.8.1.1 By Formation of Two P—P Bonds ........................................... 343 17.2.1.8.1.1.1 Method 1: Cyclization of 3-(Diphenylphosphino)-2-[(diphenylphosphino)methyl]prop-1-ene with Phosphorus Trichloride ............ 343
Table of Contents XXVII 17.2.2 Product Subclass 2: 1,2,4-Triazines C. W. Lindsley and M. E. Layton 17.2.2 Product Subclass 2: 1,2,4-Triazines ....................................... 357 17.2.2.1 Monocyclic 1,2,4-Triazines ................................................ 361 17.2.2.1.1 Synthesis by Ring-Closure Reactions ....................................... 361 17.2.2.1.1.1 By Formation of Three N—C Bonds ......................................... 361 17.2.2.1.1.1.1 Fragments N—N—C, C—C, and N ........................................... 361 17.2.2.1.1.1.1.1 Method 1: Reactions of Phenacyl Halides with Acylhydrazides .......... 361 17.2.2.1.1.1.1.1.1 Variation 1: Microwave-Assisted Reactions of Phenacyl Halides with Acylhydrazides ............................................ 362 17.2.2.1.1.1.1.2 Method 2: Condensation of 1,2-Dicarbonyl Compounds with Acylhydrazides and Ammonium Acetate ............... 363 17.2.2.1.1.1.1.2.1 Variation 1: Microwave-Assisted Condensation of 1,2-Dicarbonyl Compounds, Acylhydrazides, and Ammonium Acetate ...... 364 17.2.2.1.1.2 By Formation of Two N—C Bonds .......................................... 365 17.2.2.1.1.2.1 Fragments N—N—C—N and C—C ........................................... 365 17.2.2.1.1.2.1.1 Method 1: Reactions of 1,2-Dicarbonyl Compounds with Amidrazones . 365 17.2.2.1.1.2.1.1.1 Variation 1: Reactions of 1,2-Dicarbonyl Compounds with Semicarbazides, Thiosemicarbazides, or Selenosemicarbazides .............. 367 17.2.2.1.1.2.1.1.2 Variation 2: Reactions of 1,2-Dicarbonyl Compounds with Guanidin-2-amines or Guanidine-1,2-diamines .............. 368 17.2.2.1.1.2.1.2 Method 2: Cyclization of Hydroxyamidrazones with 1,2-Diketones ...... 368 17.2.2.1.1.2.1.3 Method 3: Cyclization of Bis(arylidene)- or Bis(alkylidene)acetone Diaminomethylenehydrazones ............................. 369 17.2.2.1.1.2.1.4 Method 4: Reactions of Guanidin-2-amines with 1,2-Dicarbonyl Equivalents ............................................... 369 17.2.2.1.1.2.1.4.1 Variation 1: Cyclization of 1,2-Diketone Monooximes with Amidrazones and Related Compounds .................................. 370 17.2.2.1.1.2.1.5 Method 5: Reactions of Acyl Nitriles with Amidrazones or Guanidin-2-amines ..................................... 371 17.2.2.1.1.2.1.6 Method 6: Synthesis from Phenacyl Bromides and 3-Methylisothiosemicarbazides ............................ 371 17.2.2.1.1.2.1.7 Method 7: Reactions of Diazo-1,2-diazoles and Electron-Rich Dipolarophiles ............................................ 371 17.2.2.1.1.2.1.7.1 Variation 1: From Activated Methylene Compounds .................... 372 17.2.2.1.1.2.2 Fragments C—C—N—N and C—N ........................................... 373 17.2.2.1.1.2.2.1 Method 1: Reactions of 2-Hydrazono Ketones with Amides and Imidates ...................................... 373 17.2.2.1.1.2.3 Fragments C—N—C—C and N—N ........................................... 373 17.2.2.1.1.2.3.1 Method 1: Reactions of a-Acylamino or a-Thioacylamino Ketones with Hydrazine, then Oxidation ............................ 373 17.2.2.1.1.2.3.2 Method 2: Cyclization of Nitrones with Hydrazine, then Oxidation ...... 374 17.2.2.1.1.2.4 Fragments N—C—C—N—N and C ........................................... 374
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: Table of Contents XXV 17.2.1.3.1.1
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
Page 61: Table of Contents LXIX 17.9.22.3 Me

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