Advances in Heterocyclic Chemistry, Vol. 30 - download pdf or read online

By Alan R. Katritzky

ISBN-10: 0120206307

ISBN-13: 9780120206308

(from preface)Volume 30 comprises seven chapters. That facing ''Furans'' via F. M. Dean updates the evaluation entitled ''The improvement of the Chemistry of Furans 1952-1963'' via F. Bosshard and С. Н. Eugster which used to be released in quantity 7.Dr. S. T. Reid has contributed the 1st of 2 sections on photochemistry of heterocycles, the current one facing that of /V-heterocycles. This updates a part of his personal past assessment ''The Photochemistry of Heterocycles'' released in 1970inVolume eleven. yet another contribution, so one can expand the updating to O- and 5-heterocycles, could be released almost immediately. Dr. A. B. Hornfeldts evaluate, entitled ''Selenophenes,'' additionally offers with an issue that used to be formerly reviewed in quantity 12 of this sequence by way of N. N. Magdesieva.The final 4 chapters of the current quantity contain subject matters new to the sequence. of them take care of particular teams of compounds (C. J. Moody on ''Azodicarbonyl Compounds'' and T. Sasaki on ''Heteroada-mantanes'') and others take care of the ''Use of Transition Organome-tallic Compounds in Heterocyclic Synthesis'' (J. L. Davidson and P. N. Preston) and ''Sulfur move Reagents''

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14’ 28 CHRISTOPHER J. MOODY [Sec. C Synthetic use can be made of the potent electrophilic properties of ADC compounds by transforming the initial adducts into heterocyclic products. For example, reaction of DEAZD with enamine 92 gives the substitution product 93 in quantitative yield. Further treatment of this initial adduct with acid, followed by base hydrolysis leads to benzoxazol-2-ones. '48-'50 Treatment of 6-amino-1,3-dimethyluracil (94, R = H) with DEAZD gives the 5substitution product (95, R = H).

Chem. 57, 2727 (1979). 239 C. Seitz and H. Hoffmann, Synthesis, 201 (1977). 2 4 0 B. Fuchs, W. D. Kwalwasser, and M. Rosenblum, Isr. J . Chem. 13, 107 (1975). 2 4 1 R. -P. Anselme, Can. J . Chem. 50, 1778 (1972). 2 4 2 J. E. Weidenborner, E. Fahr, M. J. -H. Koch, Anyew. Ed. Enyl. 12, 236 (1973). 233 2’4 ”’ Sec. VI] AZODICARBONYL COMPOUNDS 45 and derivatives, cyclic azoalkanes, and in the protection and trapping of dienes. The reactivity of ADC compounds as 271 components extends to other cycloaddition reactions, for example with 1,3-dipoles to give a wide range five-membered ring heterocycles, and with monoenes to give four-membered rings, although this latter reaction is often complicated by the fact that acyclic ADC compounds can also act as 47t components.

Ibid. 56, 1724 (1978). T. L. Gilchrist, C. W . Rees, and D. Tuddenham, unpublished result. 40 [Sec. E CHRISTOPHER J. MOODY The purine synthesis described in Section IV,C,3, in which an ADC compound acted as a source of one nitrogen atom for the heterocycle, has been extended to the synthesis of six-membered ring alloxazines. Reaction of at 180°C gives 1,3-dimethylDEAZD with 6-anilino-1,3-dimethyluraci1(124) alloxazine presumably via the initial adduct 125. ~’ 0 M e N 5 AN 0 Me (124) DEAZD M 0AN NHPh Me e N k I D Me (125) E.

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Advances in Heterocyclic Chemistry, Vol. 30 by Alan R. Katritzky


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