By Alan R. Katritzky (ed.)
Written via confirmed specialists within the box, the excellent studies mix descriptive chemistry and mechanistic perception and yield an figuring out of ways the chemistry drives the houses. quantity ninety four of Advances in Heterocyclic Chemistry commences with a evaluation of cascade reactions on heterocyclic synthesis. The bankruptcy provides a desirable array of advanced sequences which supply effective routes to a wide selection of heterocyclic structures. the second one bankruptcy is the 12th within the sequence at the natural chemistry of heterocyclic ligands in steel complexes. the current contribution bargains with the chemistry of polypyridine ligands in organomanganese and organorhenium complexes. Its present value may be measured by means of the truth that, of the approximately seven hundred references, nearly part date from the final 10 years. guidance of aminoisoxazoles and their software within the synthesis of condensed structures also are coated. within the ultimate bankruptcy, isothiazolium salts and their use in synthesis are reviewed. Many condensed S,N-heterocyclic structures are defined during this, the 1st evaluate devoted to this topic.
* up to date leads to the topic which maintains to realize value and expand
* Makes to be had to graduate scholars and learn staff in educational and commercial laboratories the newest studies on wide array of heterocyclic topics
* The sequence varieties a really massive database overlaying extensive parts of heterocyclic chemistry
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Extra resources for Advances in Heterocyclic Chemistry, Vol. 94
3,3]-SIGMATROPIC REARRANGEMENTS Of the various heterocycle-forming cascade reactions involving [3,3]-rearrangements, Overman’s use of the Aza-Cope rearrangement/Mannich cyclization sequence certainly represents the best-known example of this methodology (88JA4329, 92ACR352). Condensation of a secondary homoallylic amine containing an allylic alcohol or ether such as 218 with aldehydes produces the intermediate iminium ion 219 (Scheme 39) (79JA1310). A Cope rearrangement then provides a new iminium ion (220) that contains a transient enol, which attacks the cationic center in a Mannich fashion to deliver pyrrolidines of type 221 (79CB1913).
Sec. C] 45 THE SYNTHESIS OF HETEROCYCLES OMe OMe p -TsOH SPh PhH ∆ O OMe + SPh m-CPBA PhS OMe O PhS CH2Cl2 O O O OH 336 337 338 339 Toluene ∆ OMe OMe OMe OHC m-CPBA O CH2Cl2 O O O 342 341 340 Scheme 63 pTsOH MgSO4 OH O + H OH O AcO H OBn CH2Cl2 O H 342 341 OBn H 343 OBn O HO H Br trans-kumausyne O HO O OBn O H H Br H H O H Br kumausallene 344 345 Scheme 64 Application of the Prins-pinacol strategy also led to the synthesis of several cembranoid diterpenes. In these syntheses, BF3dOEt2 promoted the condensation of aldehyde 346 with diol 347 that generated oxonium ion 348 that underwent a subsequent Prins cyclization to provide 349 (Scheme 65) (95JA10391, 01JA9033).
In their studies, sulfoxide 204 was allowed to react with TFAA in the presence of 2,6-lutidine to give cycloadduct 205 in 50% yield and with a remarkably high diastereoselectivity (495% de). Hydrolysis of the triﬂuoroacetyl group delivered an advanced intermediate (206) that was used for the synthesis of pseudolaric acid A. III. Rearrangements and Electrocyclizations A. [2,3]-SIGMATROPIC SHIFTS The [2,3]-sigmatropic rearrangement of ammonium ylides can lead to interesting heterocycles. Although it has been known for some time that the Simmons–Smith Sec.
Advances in Heterocyclic Chemistry, Vol. 94 by Alan R. Katritzky (ed.)