Advances in Heterocyclic Chemistry, Vol. 94 by Alan R. Katritzky (ed.)

By Alan R. Katritzky (ed.)

Written through validated professionals within the box, the excellent studies mix descriptive chemistry and mechanistic perception and yield an realizing of the way the chemistry drives the houses. quantity ninety four of Advances in Heterocyclic Chemistry commences with a evaluate of cascade reactions on heterocyclic synthesis. The bankruptcy provides a desirable array of advanced sequences which supply effective routes to a large choice 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 offers with the chemistry of polypyridine ligands in organomanganese and organorhenium complexes. Its present significance will 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 lined. 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 ends up in the topic which maintains to realize significance and expand
* Makes to be had to graduate scholars and study employees in educational and commercial laboratories the most recent experiences on large choice of heterocyclic topics
* The sequence types a really huge database protecting extensive parts of heterocyclic chemistry

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BUR AND A. PADWA 56 O Bn NH O TBSOTf Et3N O + OMe Bn N Bn N O CO2Me [Sec. VI H N O CO2Me + DCE O O CH2 R R R 431a R = H 430 R = H 432 R = F F 434 431b R = H 433 R = F Scheme 78 converted into diastereomer 431b by exposure to NaOMe. A variety of unsaturated amides and unsaturated carbonyl compounds react under similar conditions to provide variously substituted piperidones. To demonstrate the synthetic utility of the s Michael addition cascade process, racemic paroxetine (Paxil ) 434 was synthesized by this method.

A] + O 59 THE SYNTHESIS OF HETEROCYCLES I Na2S2O4 NaHCO3 Rf -I Rf CH3CN/H2O N Ts 450 451a Rf = CF3 451b Rf = Cl(CF2)4 O N Ts 452a Rf = CF3 452b Rf = Cl(CF2)4 I In O N Bn + i-PrI H2O 453 O S N O Bn O N Bn 454 I In + i-PrI H2O 455 O S O N Bn 456 Scheme 80 The Et3B-initiated radical reaction of 466 with alkyl halides in the presence of both Lewis acids and a hydride donor provided cyclic ethers such as 467 via a 5-exo-trig pathway (Scheme 82) (04JOC372). Without a Lewis acid, only 467a was obtained in 39% yield, though the diastereoselectivity of the cyclization was 450:1.

B] 29 THE SYNTHESIS OF HETEROCYCLES O S S [2,3] O • 213 [3,3] O O O CCl4 O S O OAr O OAr CH2 OAr O 214 215 SH S O O O O O OAr 216 O OAr 217 Scheme 38 A novel cascade sequence was encountered during a study of the thermolysis of propargylic sulfoxide 213 which gave the rearranged structure 217 in 60–70% yield (Scheme 38) (02T10309). The cascade was initiated by a [2,3]-rearrangement of the sulfoxide, which first produced the allene intermediate 214. A subsequent [3,3]rearrangement of the transient allene then gave enone 215.

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