This article describes the author’s personal perspective on the design, production and delivery of an open-learning module in natural product chemistry. This 10 credit, level 6 module is delivered using three tutorial sessions and is assessed by three open-book tests. The study material is available to the students as both hard-copy and electronic copy.

The 2,3-dihydro-7-methyl-1H,5H-pyrido[3,2,1-ij]quinoline-1,5-dione derivatives 9 and 10 were prepared from 3-(5,7-dimethoxy-4-methyl-2-oxo-2H-quinolin-1-yl)propionitrile (6). Cyclodehydration of the amide 8 gave 1,2-dihydro-7,9-dimethoxy-6-methylpyimido[ 1,2-a]quinolin-3-one (11).

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Amidrazone 1 and the tricarbonyl derivatives 2a–c gave the triazines 3a–c, respectively, which reacted with 2,5-norbornadiene 4 in boiling ethanol yielding the corresponding novel 2,2′-bipyridines 5a–c in good yield. Triazine 6 gave the 2,2′-bipyridyl derivative 7 (65%) with compound 4 in 1,2-dichlorobenzene at 140°C.

Amides 1a–f reacted with phosphorane 3 at room temperature giving a mixture of enamine 4a–f and imine 6a–f tautomers in excellent yields. These tautomers were formed in competing reaction pathways. Silica gel promoted the conversion of 4d into 6d. Amides 1d and 1f reacted with the methyl analogue of phosphorane 3 giving tautomers 11a,b/12a,b. The β-amino acid derivatives, 13a,b, were formed from sodium borohydride reduction of imines 12a,b.

The aldehydes 7e and 7h were prepared by treatment of the 1,2,3,4-tetrahydroisoquinolines 5e and 5h,, respectively, with N-bromosuccinimide (NBS). Basic hydrolysis of compounds 7e and 7h gave the 4bH,6H-isoquino[2,1-a][3,1]benzoxazine derivatives 9 (R=H, OMe). Heterocycle 10 was obtained from the reaction of compound 5c with NBS and isolated as the ethyl derivative 11.

PM3 Semi-empirical molecular orbital calculations have been performed on terthiophene derivatives which are also heteropentalene mesomeric betaines. The ionization potentials and band-gaps have been determined in order to identify systems which might provide suitable monomers for conducting polythiophene derivatives.

The diastereoselective methylations of chiral pyridyl amide enolates 7 is described which gave products 8 and 9 in moderate diastereoisomeric excesses.

N-Trifluoroacetylanilines 6 and 7 undergo a Wittig reaction with phosphorane 2 (R = Et) giving enamine derivatives 9 and 10 respectively which are precursors to indoles 4 and quinolones 5.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The Heck reaction of methyl 2-bromobenzoate with methyl acrylate gave a mixture of alkene 1 and lactone 9. Acrylonitrile and methyl 2-bromobenzoate gave lactone 10. Ethyl 2-bromobenzoate and methyl acrylate or acrylonitrile gave the alkenes 2 and 4 respectively.

2-Bromopyridine and 2-bromo-6-methoxymethylpyridine reacted with an excess of 1-phenylethylamine at reflux giving the aminopyridine derivatives 3a and 3b respectively.

A number of substituted 1H-isoindole-1,3-(2H)-dione derivatives (phthalimides) underwent dichloromethylenation when reacted with a mixture of triphenylphosphine and carbon tetrachloride.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Lithiation of 1,2,3-triazolo[1,5-a]pyridines 4b and 4c with lithium diisopropylamide (LDA) gave the corresponding lithio derivatives 5b and 5c from which esters 6b and 6c were obtained by treatment with carbon dioxide and then dimethyl sulfate. Lithio derivatives 5a-5c reacted with DMF giving aldehydes 7a-7c. Esters 9a-9c were prepared from aldehydes 7a-7c and carbomethoxymethylenetriphenylphosphorane.