By Alan R. Katritzky (ed.)
ISBN-10: 0123739632
ISBN-13: 9780123739636
Written via proven specialists within the box, the excellent experiences mix descriptive chemistry and mechanistic perception and yield an knowing of ways the chemistry drives the houses. quantity ninety four of Advances in Heterocyclic Chemistry commences with a assessment of cascade reactions on heterocyclic synthesis. The bankruptcy offers a desirable array of advanced sequences which supply effective routes to a large choice of heterocyclic platforms. the second one bankruptcy is the 12th within the sequence at the natural chemistry of heterocyclic ligands in metal complexes. the current contribution offers with the chemistry of polypyridine ligands in organomanganese and organorhenium complexes. Its present significance may 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 application 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 structures are defined during this, the 1st assessment devoted to this topic.
* up to date ends up in the topic which maintains to realize significance and expand
* Makes on hand to graduate scholars and examine staff in educational and business laboratories the most recent studies on big range of heterocyclic topics
* The sequence types a truly mammoth database masking vast parts of heterocyclic chemistry
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Example text
Ether 467b formed with excellent diastereoselectivity (450:1), whereas ketone 467c was obtained as a 6:1-mixture of diastereomers. The disubstituted olefin 468 reacted in a similar fashion and gave 469 in 70% yield, though the diastereoselectivity (5:1) of the cyclization was significantly diminished. 5:1) diastereoselectivity. 2–6:1) diastereoselectivities. Using similar substituent placement to control relative rates, 7- and 8-membered rings were also constructed in 50–86% yields. K. BUR AND A.
The formation of tetracyclic 357 is interesting because this compound incorporates both the tetrahydropyrrolo[2,3-b]indole structure, which is found in physostigmine and related alkaloids, and the tetrahydroimidazo[1,2-a] indole skeleton, which is present in asperlicin and related natural products. V. 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.
B. PUMMERER CASCADE REACTIONS The combination of a Pummerer-based reaction (04CR2401) followed by an N-acyliminium ion cyclization in tandem to form pyrrolidine-containing ring systems represents a unique method to synthesize heterocycles. In a typical example from the Padwa laboratory, enamide 299 was treated with p-TsOH in boiling benzene to produce thionium ion 300. A subsequent Nazarov-like ring closure of 300 furnished iminium ion 301. Finally, an intramolecular Pictet–Spengler reaction with the pendant aromatic ring of 301 provided 302 as a single diastereomer in 78% yield (Scheme 56) (98JOC6778, 02JOC5928).
Advances in Heterocyclic Chemistry, Vol. 94 by Alan R. Katritzky (ed.)
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