Covering: 1 January 2001 to 31 December 2001. Previous review: J. Chem. Soc., Perkin Trans. 1, 2001, 2303.

Covering: 1 April 1998 to 30 June 1999. Previous review: J. Chem. Soc., Perkin Trans. 1, 1998, 4175.

Covering: 1 July 1999 to 31 December 2000. Previous review: J. Chem. Soc., Perkin Trans. 1, 2000, 1291.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTLigand Effects in the Rhodium(II)-Catalyzed Reactions of .alpha.-Diazoamides. Oxindole Formation is Promoted by Use Rhodium(II) Perfluorocarboxamide CatalystsDavid S. Brown, Mark C. Elliott, Christopher J. Moody, Timothy Mowlem, Joseph P. Jr. Marino, and Albert PadwaCite this: Org. Chem. 1994, 59, 9, 2447–2455Publication Date (Print):May 1, 1994Publication History Published online1 May 2002Published inissue 1...

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTDetermination of Free Acid in Presence Hydrolyzable IonsG. L. Booman, M. C. Elliott, R. B. Kimball, F. O. Cartan, and J. E. ReinCite this: Anal. Chem. 1958, 30, 2, 284–287Publication Date (Print):February 1, 1958Publication History Published online1 May 2002Published inissue 1 February 1958https://pubs.acs.org/doi/10.1021/ac60134a035https://doi.org/10.1021/ac60134a035research-articleACS PublicationsRequest reuse permissionsArticle...

Abstract This study focuses on the development of environmentally friendly and efficient synthetic routes for novel thiazolo[3,2‐ a ]pyridine‐6‐sulfonamide derivatives with potential antimicrobial properties. Using one‐pot multi‐component approach, these heterocyclic compounds were synthesized both in solution under solvent‐free mechanochemical conditions. Reactions between 1‐(4‐oxothiazolidin‐2‐ylidene)‐ N ‐phenylmethane sulfonamide, malononitrile, aryl aldehydes led to two distinct classes...

Model studies towards the synthesis of cytotoxic marine natural product diazonamide A are described. Three model 3-phenylbenzo[b]furan derivatives 5, 8 and 10 were prepared using rhodium(II) catalysed decomposition diazophenylacetate 3, Claisen rearrangement ether 7, a classical intramolecular Friedel–Crafts reaction as key steps. Only aromatic benzofuran system proved satisfactory in palladium coupling reactions; diazoacetyl(benzofuranyl)indole 18 was by Suzuki (benzofuran-7-yl)boronic acid...

Application of a diastereoselective three-component coupling to the bicyclic core batzelladine alkaloids is described. The synthesis features elaboration glutamic acid by use Eschenmoser sulfide contraction. An earlier approach also included, which shows some limitations dithiane chemistry when applied particular compounds required for this target.

Abstract

M. C. Elliott, J. Chem. Soc., Perkin Trans. 1, 1998, 4175 DOI: 10.1039/A805170D

An improved synthesis of the 1,1',2,2',3,3',4,4'-octahydro-1.1'-biisoquinoline ring system is described. The reactivity this has been investigated, including unusually high basicity parent compound and its N.N'-dimethyl derivative. resolution achieved for first time, along with development a straightforward method assaying enantiomeric purity.

Alkylidenepyrrolidines 1, 21, 24 and 26 undergo reactions with nitrile oxides nitrilimines or their precursors to give a range of novel heterocyclic compounds. With alkylidenepyrrolidine ester nitrolic acids products in which the liberated nitrous acid reacts alkylidenepyrrolidine, followed by two cycloadditions adducts 3. In contrast, hydroximoyl chlorides isoxazoles 10, presumably cycloaddition/elimination. hydrazonyl chlorides, simple acylation occurs compounds 17. sulfonyl...

It is commonly stated that alkyl groups exert an inductive electron-releasing effect when compared to hydrogen. This information has been given in numerous organic chemistry textbooks over the last 75 years. The evidence for this position weak, and does not withstand scrutiny, there some contrary position. We provide a significant body of computational data clearly show electron-withdrawing (-I) revised conflict with experimental data, since group effects are small likely be masked by...

Fifteen examples are presented showing that various modes of cyclization (5-endo, 5-exo, 6-endo, 6-exo, and 7-endo) can be used for the desymmetrization cyclohexa-1,4-dienes. All take place with complete diastereocontrol good yield.

Batzelladine C (3) is a tricyclic guanidine alkaloid of unknown stereochemistry at one centre as well absolute stereochemistry. The two possible diastereoisomers the methyl ester corresponding to this compound have been synthesised, permitting relative and be assigned.

5-Amino-3-methyl-1-phenyl-1H-pyrazole was prepared to react with various aromatic aldehydes and pyruvic acid afford 6-aryl-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carbxylic acids. The compounds were characterized by Mass, IR, 1H, 13C NMR spectra CHN analysis data. Various acids synthesized during this work also evaluated for their antibacterial activities. Some of these found be good agents.

M. C. Elliott, Contemp. Org. Synth., 1994, 1, 457 DOI: 10.1039/CO9940100457

New chiral imidazolinium salts with tunable steric features, based on a biisoquinoline template, have been developed and structurally characterised using single crystal X-ray crystallography. The trans PdI(2)(NHC)(2) complex was prepared by reaction of the parent H(4) salt Pd(OAc)(2) in presence NaI, solid state structure determined rigid, chiral, geometry found to be maintained upon ligand complexation. sterically unencumbered has give high conversion modest enantioselectivity...

Lycoposerramine A (1) is a pentacyclic alkaloid isolated in 2001 by Takayama and co-workers. concise synthesis of model compound 8 for the tetracyclic core this natural product described. Key steps include desymmetrising free-radical cyclisation 7 to give 18 spirocyclisation 26 8. Earlier approaches using novel high-yielding stereoselective anionic cyclohexa-1,4-diene are also reported.

Alkenyldihydrooxazoles undergo a highly diastereoselective formal aza-Diels–Alder reaction with aryl and arenesulfonyl isocyanates to give oxazolo[3,2-c]pyrimidines. Depending on the substitution pattern of alkenyldihydrooxazole, these compounds may then addition second equivalent isocyanate either tetrahydrooxazolo[3,2-c]pyrimidine-8-carboxamides or octahydroazeto[2,3-d]oxazolo[3,2-c]pyrimidines. The is sensitive steric electronic factors, can be prevented in some cases.

Chiral 2-alkenyloxazolines and 2-alkenylthiazolines react with isocyanates ketenes to give formal hetero-Diels-Alder adducts complete diastereocontrol. In each case an electron-rich double bond in the adduct is prone a second addition of heterocumulene. oxazoline faster than first, while thiazolines slower so that different heterocumulene can be incorporated.