Detailed table of contents (pdf)
Detailed table of contents (pdf) Detailed table of contents (pdf)
XXXII Table of Contents 17.2.2.2.5.1.2.3 Method 3: Displacement of Alkoxy Substituents ....................... 434 17.2.2.2.5.1.2.4 Method 4: Substitution of Sulfanyl and Sulfonyl Substituents ........... 434 17.2.2.2.5.1.2.5 Method 5: Substitution of Amino Groups by Diazotization ............. 435 17.2.2.2.5.2 Addition Reactions ....................................................... 435 17.2.2.2.5.2.1 Method 1: O-Alkylation of 1,2,4-Benzotriazin-3(4H)-one 1-Oxides ...... 435 17.2.2.2.5.2.2 Method 2: Alkylation of 3-Sulfanylphenanthro[9,10-e][1,2,4]triazine .... 436 17.2.2.2.5.2.3 Method 3: N-Alkylation of 1,2,4-Benzotriazin-3-amine 1-Oxide ......... 437 17.2.2.2.5.2.4 Method 4: Oxidation of 1,2,4-Benzotriazines .......................... 437 17.2.2.2.5.2.4.1 Variation 1: Oxidation of 1,2,4-Benzotriazine 1-Oxides to 1,2,4-Benzotriazine 1,4-Dioxides ........................... 438 17.2.2.2.5.3 Modification of Substituents .............................................. 438 17.2.2.2.5.3.1 Method 1: Oxidation of 3-Ethyl-1,2,4-benzotriazine to 3-Acetyl-1,2,4-benzotriazine ............................... 438 17.2.2.2.5.3.2 Method 2: Oxidation of 3-Methylsulfanyl-1,2,4-benzotriazine .......... 439 17.2.2.2.5.3.3 Method 3: Oxidation of 3-Hydrazinyl-1,2,4-benzotriazine .............. 439 17.2.2.2.5.3.4 Method 4: Reduction of 3-Azido-1,2,4-benzotriazine .................. 440 17.2.2.2.5.3.5 Method 5: Reaction of 3-Hydrazinyl-1,2,4-benzotriazines .............. 440 17.2.3 Product Subclass 3: 1,3,5-Triazines and Phosphorus Analogues S. von Angerer 17.2.3 Product Subclass 3: 1,3,5-Triazines and Phosphorus Analogues .......... 449 17.2.3.1 1,3,5-Triazines ............................................................ 452 17.2.3.1.1 Synthesis by Ring-Closure Reactions ....................................... 452 17.2.3.1.1.1 By Formation of Three N—C Bonds ......................................... 452 17.2.3.1.1.1.1 Fragments N—C, N—C, and N—C ........................................... 452 17.2.3.1.1.1.1.1 Method 1: Trimerization of Nitriles .................................... 453 17.2.3.1.1.1.1.1.1 Variation 1: Synthesis of Unsubstituted 1,3,5-Triazine ................... 453 17.2.3.1.1.1.1.1.2 Variation 2: Synthesis of 2,4,6-Trialkyl-1,3,5-triazines ................... 453 17.2.3.1.1.1.1.1.3 Variation 3: Synthesis of 2,4,6-Triaryl-1,3,5-triazines .................... 455 17.2.3.1.1.1.1.1.4 Variation 4: Synthesis of 2,4,6-Trihalo-1,3,5-triazines ................... 457 17.2.3.1.1.1.1.1.5 Variation 5: Synthesis of 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione and Derivatives ............................................... 458 17.2.3.1.1.1.1.1.6 Variation 6: Synthesis of 1,3,5-Triazine-2,4,6-triamines .................. 459 17.2.3.1.1.1.1.1.7 Variation 7: Cotrimerization of Two Different Nitriles ................... 460 17.2.3.1.1.1.1.1.8 Variation 8: Cotrimerization of Disubstituted Cyanamides with Formamides .............................................. 462 17.2.3.1.1.1.1.1.9 Variation 9: Cotrimerization of Two Nitriles with Guanidine ............. 463 17.2.3.1.1.1.1.1.10 Variation 10: Cotrimerization of Two Cyanates with 2-Alkyl- or 2-Arylisothiourea ......................................... 463 17.2.3.1.1.1.1.2 Method 2: Trimerization of Imidates .................................. 464 17.2.3.1.1.1.1.3 Method 3: Trimerization of Amidines ................................. 465 17.2.3.1.1.1.1.4 Method 4: Trimerization of Urea ...................................... 467 17.2.3.1.1.1.1.5 Method 5: Cyclocondensation of Imidates with Amidines .............. 467 17.2.3.1.1.1.2 Fragments N—C—N, N—C, and C ........................................... 469
Table of Contents XXXIII 17.2.3.1.1.1.2.1 Method 1: Reaction of 2-Alkylisothiouronium Salts with Formic Acid Derivatives ............................................... 469 17.2.3.1.1.1.2.2 Method 2: Reaction of Substituted Guanidines with Dimethylformamide Acetals ................................................... 470 17.2.3.1.1.1.2.3 Method 3: Reaction of Amidines with Carboxylates .................... 471 17.2.3.1.1.1.2.4 Method 4: Reaction of Amidines with Phosgene ....................... 472 17.2.3.1.1.1.2.5 Method 5: Reaction of Urea with Benzonitriles ........................ 473 17.2.3.1.1.1.3 Fragments N—C—N—C, N, and C ........................................... 473 17.2.3.1.1.1.3.1 Method 1: One-Pot Tandem Reaction of Aldehydes with Ammonia and Guanidine-1-carbonitrile ................................... 473 17.2.3.1.1.2 By Formation of Two N—C Bonds .......................................... 474 17.2.3.1.1.2.1 Fragments N—C—N—C and N—C ........................................... 474 17.2.3.1.1.2.1.1 Method 1: Reaction of Dimethyl Cyanodithioimidocarbonate with Amides ................................................... 474 17.2.3.1.1.2.1.2 Method 2: Reaction of 2-Arylisourea-1-carbonitriles with Aryl Cyanates . 475 17.2.3.1.1.2.1.3 Method 3: Reaction of N-Cyanoimidates with Cyanamide .............. 475 17.2.3.1.1.2.1.4 Method 4: Reaction of Guanidine-1-carbonitrile with Nitriles ........... 475 17.2.3.1.1.2.1.5 Method 5: Reaction of Imidodicarbonimidates with Aryl Cyanates ...... 477 17.2.3.1.1.2.1.6 Method 6: Reactions of Guanidine-2-carbaldehydes with N-Formylformimidamide .................................. 478 17.2.3.1.1.2.1.7 Method 7: Reaction of 1-Acylguanidines with Nitriles .................. 478 17.2.3.1.1.2.2 Fragments N—C—N and C—N—C ........................................... 479 17.2.3.1.1.2.2.1 Method 1: Reaction of Cyanodithioimidocarbonates with Amidine Derivatives ............................................... 479 17.2.3.1.1.2.2.2 Method 2: Reaction of 2-Phenylisourea-3-carbonitriles with Amidines .. 481 17.2.3.1.1.2.2.3 Method 3: Reaction of N-Cyanoimidates with Amidine Derivatives ..... 481 17.2.3.1.1.2.2.4 Method 4: Reaction of N-Functionalized Imidoyl Chlorides with Amidine Derivatives ............................................... 482 17.2.3.1.1.2.2.4.1 Variation 1: Reaction of N-(1-Chloroalkylidene)carbamoyl Chlorides ..... 482 17.2.3.1.1.2.2.4.2 Variation 2: Reaction of N-Polychloroalkyl-Substituted Imidoyl Chlorides . 483 17.2.3.1.1.2.2.4.3 Variation 3: Reaction of N-(Trichlorovinyl)benzimidoyl Chlorides ......... 484 17.2.3.1.1.2.2.4.4 Variation 4: Reaction of N-Acylchloroformimidates ..................... 485 17.2.3.1.1.2.2.4.5 Variation 5: Reaction of N-Acylchloroformimidamides .................. 485 17.2.3.1.1.2.2.4.6 Variation 6: Reaction of 1,3-Diamino-1-chloro-2-azapropenylium Salts ... 486 17.2.3.1.1.2.2.5 Method 5: Reaction of Imidodicarbonates with N 1 -tert-Butyl-Substituted Amidines ................................................. 487 17.2.3.1.1.2.2.6 Method 6: Reaction of Acyldithioimidocarbonates with Amidine Derivatives ............................................... 488 17.2.3.1.1.2.2.7 Method 7: Reaction of N 2 -Acyl-1H-benzotriazole-1-carboximidamides with Urea or Thiourea ..................................... 489 17.2.3.1.1.2.2.8 Method 8: Reaction of N-Acylimidates or N-Acylthioimidates with Amidine Derivatives ....................................... 489 17.2.3.1.1.2.2.9 Method 9: Reaction of N 2 -Acylamidines with Amidine Derivatives ...... 491 17.2.3.1.1.2.2.10 Method 10: Reaction of Acyl Isothiocyanates with Amidine Derivatives .. 493 17.2.3.1.1.2.2.11 Method 11: Reaction of N-Acylthioamides with Amidine Derivatives ..... 493
- Page 1 and 2: Table of Contents IX Volume 17: Six
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- 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
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- 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
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- Page 23: Table of Contents XXXI 17.2.2.2.1.4
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- 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
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XXXII Table <strong>of</strong> Contents<br />
17.2.2.2.5.1.2.3 Method 3: Displacement <strong>of</strong> Alkoxy Substituents ....................... 434<br />
17.2.2.2.5.1.2.4 Method 4: Substitution <strong>of</strong> Sulfanyl and Sulfonyl Substituents ........... 434<br />
17.2.2.2.5.1.2.5 Method 5: Substitution <strong>of</strong> Amino Groups by Diazotization ............. 435<br />
17.2.2.2.5.2 Addition Reactions ....................................................... 435<br />
17.2.2.2.5.2.1 Method 1: O-Alkylation <strong>of</strong> 1,2,4-Benzotriazin-3(4H)-one 1-Oxides ...... 435<br />
17.2.2.2.5.2.2 Method 2: Alkylation <strong>of</strong> 3-Sulfanylphenanthro[9,10-e][1,2,4]triazine .... 436<br />
17.2.2.2.5.2.3 Method 3: N-Alkylation <strong>of</strong> 1,2,4-Benzotriazin-3-amine 1-Oxide ......... 437<br />
17.2.2.2.5.2.4 Method 4: Oxidation <strong>of</strong> 1,2,4-Benzotriazines .......................... 437<br />
17.2.2.2.5.2.4.1 Variation 1: Oxidation <strong>of</strong> 1,2,4-Benzotriazine 1-Oxides to<br />
1,2,4-Benzotriazine 1,4-Dioxides ........................... 438<br />
17.2.2.2.5.3 Modification <strong>of</strong> Substituents .............................................. 438<br />
17.2.2.2.5.3.1 Method 1: Oxidation <strong>of</strong> 3-Ethyl-1,2,4-benzotriazine to<br />
3-Acetyl-1,2,4-benzotriazine ............................... 438<br />
17.2.2.2.5.3.2 Method 2: Oxidation <strong>of</strong> 3-Methylsulfanyl-1,2,4-benzotriazine .......... 439<br />
17.2.2.2.5.3.3 Method 3: Oxidation <strong>of</strong> 3-Hydrazinyl-1,2,4-benzotriazine .............. 439<br />
17.2.2.2.5.3.4 Method 4: Reduction <strong>of</strong> 3-Azido-1,2,4-benzotriazine .................. 440<br />
17.2.2.2.5.3.5 Method 5: Reaction <strong>of</strong> 3-Hydrazinyl-1,2,4-benzotriazines .............. 440<br />
17.2.3 Product Subclass 3: 1,3,5-Triazines and Phosphorus Analogues<br />
S. von Angerer<br />
17.2.3 Product Subclass 3: 1,3,5-Triazines and Phosphorus Analogues .......... 449<br />
17.2.3.1 1,3,5-Triazines ............................................................ 452<br />
17.2.3.1.1 Synthesis by Ring-Closure Reactions ....................................... 452<br />
17.2.3.1.1.1 By Formation <strong>of</strong> Three N—C Bonds ......................................... 452<br />
17.2.3.1.1.1.1 Fragments N—C, N—C, and N—C ........................................... 452<br />
17.2.3.1.1.1.1.1 Method 1: Trimerization <strong>of</strong> Nitriles .................................... 453<br />
17.2.3.1.1.1.1.1.1 Variation 1: Synthesis <strong>of</strong> Unsubstituted 1,3,5-Triazine ................... 453<br />
17.2.3.1.1.1.1.1.2 Variation 2: Synthesis <strong>of</strong> 2,4,6-Trialkyl-1,3,5-triazines ................... 453<br />
17.2.3.1.1.1.1.1.3 Variation 3: Synthesis <strong>of</strong> 2,4,6-Triaryl-1,3,5-triazines .................... 455<br />
17.2.3.1.1.1.1.1.4 Variation 4: Synthesis <strong>of</strong> 2,4,6-Trihalo-1,3,5-triazines ................... 457<br />
17.2.3.1.1.1.1.1.5 Variation 5: Synthesis <strong>of</strong> 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione and<br />
Derivatives ............................................... 458<br />
17.2.3.1.1.1.1.1.6 Variation 6: Synthesis <strong>of</strong> 1,3,5-Triazine-2,4,6-triamines .................. 459<br />
17.2.3.1.1.1.1.1.7 Variation 7: Cotrimerization <strong>of</strong> Two Different Nitriles ................... 460<br />
17.2.3.1.1.1.1.1.8 Variation 8: Cotrimerization <strong>of</strong> Disubstituted Cyanamides with<br />
Formamides .............................................. 462<br />
17.2.3.1.1.1.1.1.9 Variation 9: Cotrimerization <strong>of</strong> Two Nitriles with Guanidine ............. 463<br />
17.2.3.1.1.1.1.1.10 Variation 10: Cotrimerization <strong>of</strong> Two Cyanates with 2-Alkyl- or<br />
2-Arylisothiourea ......................................... 463<br />
17.2.3.1.1.1.1.2 Method 2: Trimerization <strong>of</strong> Imidates .................................. 464<br />
17.2.3.1.1.1.1.3 Method 3: Trimerization <strong>of</strong> Amidines ................................. 465<br />
17.2.3.1.1.1.1.4 Method 4: Trimerization <strong>of</strong> Urea ...................................... 467<br />
17.2.3.1.1.1.1.5 Method 5: Cyclocondensation <strong>of</strong> Imidates with Amidines .............. 467<br />
17.2.3.1.1.1.2 Fragments N—C—N, N—C, and C ........................................... 469
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