Chemistry of Heterocyclic Compounds: Synthesis of Fused by Gwynn P. Ellis

By Gwynn P. Ellis

This booklet classifies tools of synthesizing a heterocyclic ring that's fused to a different ring. type relies at the useful staff or teams found in the substrate, each one bankruptcy being dedicated to the reactions of a specific pair of teams. The teams are prepared alphabetically which will be came upon simply. The e-book allows the reader to find references (over 2000 are incorporated) to the conversion of a wide selection of useful teams into heterocyclic jewelry of 5 to 8 atoms. every one cyclization is proven as an equation which incorporates concise information or reagents, stipulations, and yields. because the type of every cyclization is predicated at the practical teams concerned, finding the appropriate reference is autonomous of the id of the hoop within the substrate. This simplifies the hunt for the correct reference.Content:
Chapter 1 creation (pages 1–7):
Chapter 2 Acetal or Aldehyde and Amine (pages 8–16):
Chapter three Acetal and Ring?Carbon or Ring?Nitrogen (pages 17–20):
Chapter four Acylamine and Aldehyde or Ketone (pages 21–23):
Chapter five Acylamine and Amine (pages 24–28):
Chapter 6 Acylamine or Carbamate and Carboxamide or Nitrile (pages 29–31):
Chapter 7 Acylamine and Carboxylic Acid or Ester (pages 32–36):
Chapter eight Acylamine or Amine and Ether or Thioether (pages 37–39):
Chapter nine Acylamine, Acylhydrazine or Amine and Halogen (pages 40–47):
Chapter 10 Acylamine or Amine and Hydroxy or Thiol (pages 48–59):
Chapter eleven Acylamine, Amine or Diazonium Salt and lActam Carbonyl (pages 60–67):
Chapter 12 Acylamine or Amine and Methylene (pages 68–73):
Chapter thirteen Acylamine or Amine and Nitrile (pages 74–82):
Chapter 14 Acylamine, Acylhydrazine, Amine or Carbamate and Nitro (pages 83–85):
Chapter 15 Acylamine or Amine and Nitroso or N?Oxide (pages 86–88):
Chapter sixteen Acylamine, Acyloxy, Amine or Hydroxy and Phosphorane (pages 89–91):
Chapter 17 Acylamine or Acylhydrazine and Ring?Carbon or Ring?Sulphur (pages 92–97):
Chapter 18 Acylamine or Acylhydrazine and Ring?Nitrogen (pages 98–101):
Chapter 19 Acylamine or Amine and Sulphonamide, Thioureide or Ureide (pages 102–104):
Chapter 20 Acylamine or Amine and Thiocyanate (pages 105–106):
Chapter 21 Acyl Halide and Ring?Carbon or Ring?Nitrogen (pages 107–109):
Chapter 22 Aldehyde or Ketone and Alkene or Alkyne (pages 110–112):
Chapter 23 Aldehyde or Ketone and Azide (pages 113–115):
Chapter 24 Aldehyde or Ketone and Carbamate (pages 116–117):
Chapter 25 Aldehyde or Ketone and Carboxamide or Hydrazide (pages 118–119):
Chapter 26 Aldehyde or Ketone and Carboxylic Acid or Ester (pages 120–124):
Chapter 27 Aldehyde or Ketone and Ether or Thioether (pages 125–129):
Chapter 28 Aldehyde or Ketone and Halogen (pages 130–136):
Chapter 29 Aldehyde and Hydroxy, Thiol or Thiocyanate (pages 137–142):
Chapter 30 Aldehyde and Ketone; Dialdehyde or Diketone (pages 143–153):
Chapter 31 Aldehyde or Ketone and Methylene (pages 154–156):
Chapter 32 Aldehyde or Ketone and Nitrile (pages 157–158):
Chapter 33 Aldehyde or Ketone and Nitro, Nitroso or N?Oxide (pages 159–160):
Chapter 34 Aldehyde or different Carbonyl and Phosphorane (pages 161–165):
Chapter 35 Aldehyde or Ketone and Ring?Carbon (pages 166–174):
Chapter 36 Aldehyde or Ketone and Ring?Nitrogen (pages 175–179):
Chapter 37 Alkene or Alkyne and Arnine or Nitro (pages 180–183):
Chapter 38 Alkene or Alkyne and Carboxylic Acid or its spinoff (pages 184–186):
Chapter 39 Alkene or Alkyne and Halogen (pages 187–188):
Chapter forty Alkene or Alkyne and Hydroxy, Thiol or Ethqr (pages 189–192):
Chapter forty-one Alkene, Methylene, Ring?Carbon, or Ring?Nitrogen and Lactam Carbonyl (pages 193–196):
Chapter forty two Alkene or Alkyne and Methylene, Ring?Carbon or Ring?Nitrogen (pages 197–202):
Chapter forty three Arnidine and Arnine, Carboxylic Acid, Ester, Hydroxy, Methylene or Nitro (pages 203–205):
Chapter forty four Arnidine and Ring?Carbon or Ring?Nitrogen (pages 206–207):
Chapter forty five Arnine and Azo or Diazo (pages 208–209):
Chapter forty six Arnine and Carboxarnide or Thiocarboxarnide (pages 210–218):
Chapter forty seven Arnine and Carboxylic Acid (pages 219–225):
Chapter forty eight Arnine and Carboxylic Ester (pages 226–238):
Chapter forty nine Arnine and Enarnine (pages 239–240):
Chapter 50 Amine and Hydrazide or Hydrazine (pages 241–245):
Chapter fifty one Amine and Hydrazone or Irnine (pages 246–250):
Chapter fifty two Amine and Ketone (pages 251–261):
Chapter fifty three Amine and Ring?Carbon or Ring?Sulphur (pages 262–275):
Chapter fifty four Amine and Ring?Nitrogen (pages 276–291):
Chapter fifty five Azide and Azo or Nitro (pages 292–293):
Chapter fifty six cover and a Carboxylic Acid or its spinoff (pages 294–296):
Chapter fifty seven Azide and Methyl, Methylene or Methine (pages 297–298):
Chapter fifty eight Azide and Ring?Carbon (pages 299–303):
Chapter fifty nine Azide and Ring?Nitrogen (pages 304–306):
Chapter 60 Azo or Triazene and Carbarnate, Carboxylic Acid, Ester or Nitrile (pages 307–308):
Chapter sixty one Carbarnate or Cureide and Ring?Carbon or Ring?nitrogen (pages 309–316):
Chapter sixty two Carboxarnide and one other Carboxylic Acid by-product (pages 317–319):
Chapter sixty three Carboxarnide or Sulphonamide and Diazonium Salt or Diazo (pages 320–321):
Chapter sixty four Carboxamide, Hydroxamic Acid, Hydrazide, Nitrile or Ureide and Hydroxy or Ether (pages 322–327):
Chapter sixty five Carboxarnide or Nitrile and Ring?Carbon or Ring?Nitrogen (pages 328–335):
Chapter sixty six Carboxylic Acid or its spinoff and Halogen (pages 336–346):
Chapter sixty seven Carboxylic Acid or Ester and Hydrazide or Hydrazine (pages 347–349):
Chapter sixty eight Carboxylic Acid, Acyl Chloride or Ester and Hydroxy or Ether (pages 350–356):
Chapter sixty nine Carboxylic Acid or its by-product and Lactam Carbonyl or Isocyanate (pages 357–361):
Chapter 70 Carboxylic Acid, Ester, Nitrile or Isonitrile and Methylene (pages 362–369):
Chapter seventy one Carboxylic Acid Halide or Ester and Nitrile (pages 370–372):
Chapter seventy two Carboxylic Acid, its by-product or Lactam Carbonyl and Nitro or Ureide (pages 373–377):
Chapter seventy three Carboxylic Acid or Ester and Ring?Carbon (pages 378–386):
Chapter seventy four Carboxylic Acid or Ester and Ring?Nitrogen (pages 387–393):
Chapter seventy five Carboxylic Acid or its spinoff and a Sulphinic or Sulphonic Acid spinoff (pages 394–397):
Chapter seventy six 1,2?Diamine (pages 398–425):
Chapter seventy seven 1,3?, 1,4? and 1, 5?Diamine (pages 426–432):
Chapter seventy eight Diazo or Diazonium Salt and Methylene (pages 433–435):
Chapter seventy nine Diazo or Diazonium Salt anD Ring?Carbon or Ring?Nitrogen (pages 436–441):
Chapter eighty Dicarboxylic Acid, its Anhydride, Diacyl Halide, Diester or Dihydrazide (pages 442–445):
Chapter eighty one Dihalogen (pages 446–450):
Chapter eighty two Diol or Dithiol (pages 451–455):
Chapter eighty three Dinit Rile (pages 456–457):
Chapter eighty four Di?Ring?Carbon or Di?Ring?Nitrogen (pages 458–463):
Chapter eighty five Enamine and Ester or Ketone (pages 464–468):
Chapter 86 Enamine and a Non?Carbonyl team (pages 469–472):
Chapter 87 Ether or Thioether and Ring?Carbon or Ring?Nitrogen (pages 473–476):
Chapter 88 Halogen and Hydroxy or Thiol (pages 477–484):
Chapter 89 Halogen and Lactam Carbonyl or a Sulphur?Containing team (pages 485–488):
Chapter ninety Halogen and Methylene or Ring?Carbon (pages 489–491):
Chapter ninety one Halogen and Nitro (pages 492–496):
Chapter ninety two Halogen and Ring?Nitrogen (pages 497–502):
Chapter ninety three Hydrazide or Hydrazine and Nitro or Ring?Nitrogen (pages 503–507):
Chapter ninety four Hydrazine and Ring?Carbon or Ring?Nitrogen (pages 508–521):
Chapter ninety five Hydrazone or Oxime and Ring?Carbon or Ring?Nitrogen (pages 522–527):
Chapter ninety six Hydroxy and Ketone or Lactam Carbonyl (pages 528–532):
Chapter ninety seven Hydroxy and Methylene (pages 533–536):
Chapter ninety eight Hydroxy and Nitro, Nitroso or Ring?Nitrogen (pages 537–539):
Chapter ninety nine Hydroxy or Thiol and Ring?Carbon (pages 540–546):
Chapter a hundred Imine and Hydroxy, Ring?Carbon or Ring?Nitrogen (pages 547–549):
Chapter a hundred and one Isocyanate or Isothiocyanate and Methylene, Ring?Carbon or Ring?Nitrogen (pages 550–553):
Chapter 102 Ketone and Lactam Carbonyl (pages 554–557):
Chapter 103 Methylene and Nitro or Nitroso (pages 558–561):
Chapter 104 Methylene and Ring?Carbon or Ring?Nitrogen (pages 562–567):
Chapter one hundred and five Nitro or N?Oxide and Ring?Carbon or Ring?Nitrogen (pages 568–570):
Chapter 106 Ring?Carbon and Ring?Nitrogen (pages 571–572):
Chapter 107 Ring?Nitrogen and Thiol or Lactam Thiocarbonyl (pages 573–577):

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Extra info for Chemistry of Heterocyclic Compounds: Synthesis of Fused Heterocycles, Volume 47

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37 37 37 38 38 38 38 38 38 I. FORMATION OF A FIVE-MEMBERED RING 1. Pyrazole In this cyclization, an anion from a -COCH2COor a -CH,COOH displaces a methylthio group and the amine attacks the carbonyl to form a pyrazole ring. R’=Me,Pr,HO,Phi Pyrazolo[ 1 ,S-U]pyridine R L Ms,MeO,E t O 2. 1,2, QTriazole A methylthio groupattached to n-deficient ring is usually readily displaced and in this base-catalysed reaction one molar proportion each of base and aryl nitrile react with the rnethyithio-arnine to form a triazole ring.

FORMATION OF A SEVEN-MEMBERED RING 1. 1,eDiazepine or 1, 4-Diazepin3-one When the side-chain contains a suitable number of atoms, the diazepine is formed in good yield. COOEt H I u R =Me,Ph Benzofuro[3,2-8]- 1,4- diazepine saNHCocH2 Nol,Me2C0, 13. COPh + NH3 65%* Ph Thisno[3,4 -S]- I , 4 - diazepin- 2 -one Chemistry of Heterocyclic Compounds, Volume47 G. P. Ellis Copyright 0 1987 by John Wiley & Sons, Ltd. CHAPTER 5 Acylamine and Amine I. Formation of a Five-membered Ring I . Imidazole 2. Imidazol-2-one 3.

Pyran 4. 4-Oxazine 5. 1,4-0xazin-2- or -3-one (or -thione) 6. 1,3- or I , 4-Thiazine 7. 4-Thiazin-2- or -3-one 111. Formation of a Seven-membered Ring I . 1,4-Oxazepine-5,7-dione 2. 1,4-Thiazepine or 1,4-Thiazepin-7-one I. 1. FORMATION OF A FIVE-MEMBERED RING 1. Pyrrole or Pyrrol-2-one Cyclocondensation under dehydrating conditions converts 4-aminoalcohols into fused pyrroles in moderate yields; since phosphorus pentachloride is also an effective reagent, the reaction may then be dehydrohalogenation.

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