Chapter VI Fused 5/6 Ring structures with additional Heteroatoms (pages 749–859):
Chapter VII Fused 5/6 Ring platforms with 3 additional Heteroatoms (pages 861–925):
Chapter VIII Fused 5/6 Ring platforms with 4 or extra additional Heteroatoms (pages 927–948):
Chapter IX Fused 5/6 Ring structures with Bridgehead Nitrogen Atoms (pages 949–956):
Chapter X Fused 5/7 and bigger Ring structures (pages 957–1000):
Chapter XI Fused 6/6 Ring platforms without additional Heteroatom (pages 1001–1140):
Chapter XII Fused 6/6 Ring platforms with One additional Heteroatom (pages 1141–1214):
Chapter XIII Fused 6/6 Ring structures with or extra additional Heteroatoms (pages 1215–1239):
Chapter XIV Fused 6/6 Ring platforms with Bridgehead Nitrogen Atoms (pages 1241–1246):
Chapter XV Fused 6/7 and bigger Ring platforms (pages 1247–1264):
Chapter XVI Bridged 3/4 via 5/6 Ring platforms (pages 1267–1320):
Chapter XVII Bridged 6/6 Ring structures (pages 1321–1402):
Chapter XVIII Bridged 6/7 and bigger Ring structures (pages 1403–1421):
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Extra resources for Chemistry of Heterocyclic Compounds: Heterocyclic Systems with Bridgehead Nitrogen Atoms, Part 2, Volume 15
Phot.. 47,2 (1952). 17. Pat. 2,739,964. 18. Giambrone, Boll. sci. fat. chim. ind. B o ~ o ~ M 11,, 86 (1953); Chem. Abstracts, 49, 4662 (1955). s&y>: 10 A-505. 4H-Pyrimido[2,1-b]bcnzothiazolc I l\ 5 6 4 This nucleus has also been called 4,ll-dihydro- 1,l l-diaza-9-thiafluorem. Schrader indicated that acylacetamides such as I could be dehydrated to I I, but no details were reported. ' 0 k Fused 5/6 Ring Systems with Two Extra Heteroatoms 787 By heating 2-aminobenzothiazoles with paminocrotonic ester, Qntaki and Petrov2 prepared a group of compounds of structure H I (R = H, m.
Dehydrochlorination of VI with alcoholic potash yielded the so-called y-Korper, which was assigned structure VII. However, structure VIII would seem to be an alternative possibility. The only authentic 7-mOnO- - cH3yx3.. H HCI H /I 0 0 VII) CI CH, -Ha __+ YOH (VIII) hydroxy derivative appears to be X , obtained6 by reacting IX with ethoxymethylenemalonic ester. 5-Monohydroxy derivatives (XI) have been obtained 7 7 8 similarly by condensing 2-aminoimidazoles (such as IX) with Bketoesters. Prokof'ev and his co-workers foundg-I ' that guanidine acids such as XI1 may be converted directly into XIV, or may first be cyclized to the 2-amino-4-imidazolinone (XI 11) and this condensed Chapter VI 804 HZN 'y"),' '- C6H6 C,H, J RCOCH,COOC,H, OH with a Fketoester to yield XIV.
The condensation of 2-chlorothiazoles with anthranilic acid, a ynthesis designed to give only the linear product (VIII), was next tudied. ). Since the products prepared from the 2-chlorothiazoles were presumed to be linear (VIII), it was suggested"-12 that the earlier products were the angular (IX) isomers. The condensation of 2-chlorobcnzoic acid with 2-aminothiazoline was reported unsuccessful. T h e condensation of anthranilic acid with ally1 mustard oil yields a product thought to be 3-allyl-2-mercaptoquinazolone or 2,3dihydro-2-methyithiazolo[2,3-b]quinazolin-5-one.
Chemistry of Heterocyclic Compounds: Heterocyclic Systems with Bridgehead Nitrogen Atoms, Part 2, Volume 15