Chapter I Fused 3?Membered Ring structures (pages 7–34):
Chapter II Fused 4?Membered Ring structures (pages 35–62):
Chapter III Fused 5/5 Ring platforms (pages 63–237):
Chapter IV Fused 5/6 Ring structures without additional Heteroatom (pages 239–449):
Chapter V Fused 5/6 Ring structures with one additional Heteroatom (pages 451–747):
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Extra resources for Chemistry of Heterocyclic Compounds: Heterocyclic Systems with Bridgehead Nitrogen Atoms, Part 1, Volume 15
504,l (1933). 5. , 514,267 (1934). 2 A-43. 2,0] hep tane. I. 510 70 - l,CH2.. N 6kx2- 3 I AH-cH, 5 2 4 The alkaloids’ stachydrine (I, R = H) and betonicine (I, R = OH) are the closest approach to examples of this nucleus. Fused 4-Membered Ring Systems 39 Reference 1. Marion, “The Pyrrolidine Alkaloids,” in Manske and Holmes, The Aikaiozds, Academic Press, New York, Vol. 1, 1950, p. 91. 2 A-44. 0]heptane CHrN I CH,6 I CH5 S 4 All of the examples of this ring system were prepared in connection with work upon the penicillins, and all contain a 6 0 x 0 group.
Chim. , 30,1I, 460 (1900). 1 A-25. 01hexane. I. 445 6/N-o HN e 1 YH 5 4 13 \ CH-CH, Hydrolysis of I yielded a product (m. 175") which was called &fulminurzc acid umide and was formulated as 11. The corresponding acid (111, m. 196") was called imidofuroxamcarboxylic acid or 4,Sendoirnino- 1,2,5-oxadia~olzne-3carboxylic acid. Compound 111 was a strong acid, which, by the Fischer-Speyer method, gave an ethyl ester (m. 103-4") and, with nitrous acid, yielded a nitroso derivative (explodes at 133") thought to be IV.
A. 227-32' d. m. 183" (187O). m. 210O. m. 147-8'. Red, m. 247' (245 ', 232 '). 15 1 15 3,4,16,17 -255 C18H12BrZN204 H C18H14N204 H C ~ ~ H ~ ~ B CH~ C19H16N204 H C~0H16Br2N204 H C21H18N204 H C2lHzoN2O4 H 2-8-DibromoEt None n-Pr N Z O 2,SDibromo~ n-Pr None i-Bu 2,8-Dibromoi-Bu None M e 2,4,8,10Et Tetra- methyl- Refs. Properties '. 12 12,14 References 1. , 15,2093 (1882). , 54,1221 (1921). , 55,3180 (1922). , 56,2110 (1923). , 58,680 (1925). , 58,686 (1925). , 40, 1291 (1907). 2. 3. 4. 5. 6. 7. 8.