By Alan R. Katritzky (ed.)
Written by means of validated gurus within the box, the excellent experiences mix descriptive chemistry and mechanistic perception and yield an figuring out of the way the chemistry drives the homes. 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 wide selection of heterocyclic structures. the second one bankruptcy is the 12th within the sequence at the natural chemistry of heterocyclic ligands in metal complexes. the current contribution bargains with the chemistry of polypyridine ligands in organomanganese and organorhenium complexes. Its present value might be measured via 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 platforms also are lined. within the ultimate bankruptcy, isothiazolium salts and their use in synthesis are reviewed. Many condensed S,N-heterocyclic platforms are defined during this, the 1st overview devoted to this topic.
* up to date ends up in the topic which keeps to achieve value and expand
* Makes to be had to graduate scholars and study employees in educational and business laboratories the newest studies on wide array of heterocyclic topics
* The sequence varieties a really monstrous database protecting broad components of heterocyclic chemistry
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Additional resources for Advances in Heterocyclic Chemistry, Vol. 94
Thus, nitro aromatics of type 387 undergo an ironmediated reduction to furnish benzo-fused heterocycles 388 in 88–98% yield (Scheme 72) (00JOC2847). K. BUR AND A. PADWA 52 [Sec. B triggered a cyclization reaction to produce tetrahydrofuran derivatives 390–394 in 70–90% yields (93SC1009). A variant of the Krapcho decarbalkoxylation (73TL957) linked to a Michael reaction of the intermediate enolate was reported to occur onto a tethered enoate moiety (98JOC144). Thus, the reaction of 395 with LiCl in dimethyl2-imidazolidinone (DMEU) at 120 1C selectively excised the methyl ester and the resulting enolate then underwent addition to the neighboring enone moiety to furnish a 3:1-mixture of the substituted tetrahydrofurans 396 and 397 in 67% combined yield.
1,4-Additions A. MICHAEL ADDITION-INITIATED SEQUENCES Dihydropyridine derivatives can be formed from a cascade sequence wherein conjugate addition of enaminoesters occur with a,b-unsaturated carbonyl compounds Sec. A] 47 THE SYNTHESIS OF HETEROCYCLES Cl 10 M HCl EtOH NH O (1:2) heat HN OMe Cl 351 352 Cl OMe Cl NH3 Cl NH2 353 NH2 354 355 Scheme 66 H CO2Me N H H CO2Me H3PO4 HN NC N H HN N CO2Me HN N H 356 H N 357 O O Me N O Me HN N H N N H Me N HO Me H N NH physostigmine O asperlicin Scheme 67 followed by a subsequent condensation reaction.
K. BUR AND A. PADWA 40 O O O p-TsOH SEt N Ar R N CO2Et Me Me 299 Ar=C6H3(OMe)2 O− + R N + + SEt CO2Et Me [Sec. B Me Me 300a SEt CO2Et Me 300b O O H N SEt Me Me CO2Et + N Me 78% H SEt Me CO2Et MeO MeO OMe OMe 302 301 Scheme 56 O O O SEt Bn N CO2Me p-TsOH 61% Me H2C Bn N O p-TsOH SEt Bn N Me CO2Me 80% Me (7) O SEt CO2Me CO2Me Me 304 TMS 303 O SEt Bn N Me (8) p-TsO 305 306 This methodology was employed for the synthesis of the reported structure of the alkaloid jamtine (02OL715, 02JOC929). The key sulfoxide intermediate 307 was heated with CSA to produce several tricyclic products (98% yield) as a mixture (5:2:1:1) of diastereomers in which 308 predominated (Scheme 57).