Detailed table of contents (pdf)

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