Other 6-membered heterocycles R 0670 N,N-Dialkyl-N'-chlorosulfonyl Chloroformamidines in Heterocy... more Other 6-membered heterocycles R 0670 N,N-Dialkyl-N'-chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part 6. The Preparation of Some Fused [1,4,2,6]Dithiadiazine Dioxides.-The synthesis of three new fused dithiadiazine dioxide ring systems (III), (VIII) and (IX) is achieved by reaction of title chloroformamidines (II) with mercaptobenzimidazole (I) or mercaptotriazole (VII) as N-C-S dinucleophiles.-(CABLEWSKI, T.;
Concise synthetic protocols for a range of new 2,8-disubstituted-1,7-dicyano-3,9-diazaperylenes, ... more Concise synthetic protocols for a range of new 2,8-disubstituted-1,7-dicyano-3,9-diazaperylenes, starting from commercially available 1,5-diaminoanthraquinone, have been developed, which enable the introduction of various tertiary-amino, substituted-ethynyl, and aryl groups at the C2 and C8 positions, as well as incorporation of aryl-amino groups at the C4 and C10 positions, of the rare 3,9-diazaperylene system. This methodology should enable tuning of physical and optoelectronic properties and may find use in the discovery of new materials for organic photovoltaic devices or other organic electronic applications.
N,N-dialkyl-N-chlorosulfonylchloroformamidines 1 reacted regioselectively with 4-hydroxy-2-pyrone... more N,N-dialkyl-N-chlorosulfonylchloroformamidines 1 reacted regioselectively with 4-hydroxy-2-pyrone derivatives 2 to give 3-dialkylamino-1,1,8-trioxo-1H-1λ 6-pyrano[3,4-e][1,4,3]oxathiazines 3. Dichloride 1b reacted regioselectively with 1,3-dimethylbarbituric acid 10 to give 3-diethylamino-5,7-dimethyl-1,1,6,8-tetraoxo-1H-1λ 6-pyrimido[5,4-e]-[1,4,3]oxathiazine 11. The compounds 3 and 11 are derivatives of new ring systems.
N,N-dialkyl-N-chlorosulfonylchloroformamidines 1 reacted regioselectively with 4-hydroxy-2-pyrone... more N,N-dialkyl-N-chlorosulfonylchloroformamidines 1 reacted regioselectively with 4-hydroxy-2-pyrone derivatives 2 to give 3-dialkylamino-1,1,8-trioxo-1H-1λ 6-pyrano[3,4-e][1,4,3]oxathiazines 3. Dichloride 1b reacted regioselectively with 1,3-dimethylbarbituric acid 10 to give 3-diethylamino-5,7-dimethyl-1,1,6,8-tetraoxo-1H-1λ 6-pyrimido[5,4-e]-[1,4,3]oxathiazine 11. The compounds 3 and 11 are derivatives of new ring systems.
N,N-dialkyl-N-chlorosulfonylchloroformamidines 1 reacted regioselectively with 4-hydroxy-2-pyrone... more N,N-dialkyl-N-chlorosulfonylchloroformamidines 1 reacted regioselectively with 4-hydroxy-2-pyrone derivatives 2 to give 3-dialkylamino-1,1,8-trioxo-1H-1λ 6-pyrano[3,4-e][1,4,3]oxathiazines 3. Dichloride 1b reacted regioselectively with 1,3-dimethylbarbituric acid 10 to give 3-diethylamino-5,7-dimethyl-1,1,6,8-tetraoxo-1H-1λ 6-pyrimido[5,4-e]-[1,4,3]oxathiazine 11. The compounds 3 and 11 are derivatives of new ring systems.
An enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne... more An enantioselective synthesis of the halogenated medium-ring ether natural product (+)-obtusenyne is reported which uses the ring expansion of a seven-membered ketene acetal by means of a Claisen rearrangement to construct the core nine-membered oxygen heterocycle. The trans substituents across the ether linkage were established by using a transition-metal-catalyzed intramolecular hydrosilation reaction of an exo-cyclic enol ether. In addition, a formal synthesis of ent-obtusenyne from 2-deoxy-D-ribose is reported. A number of interesting points regarding the chemistry of medium-ring oxygen heterocycles are highlighted.
It is my pleasure to preface this Arkivoc special issue "Organic Chemistry in Australia". Colleag... more It is my pleasure to preface this Arkivoc special issue "Organic Chemistry in Australia". Colleagues engaged in organic chemistry research across this vast country from Perth to Brisbane and several places in between have contributed papers which provide for readers a flavor of the areas of research being conducted "down under". The assembly of this collection of papers led me to reflect on the changing landscape of organic chemistry in Australia since my time as a student at The University of Adelaide 30 years ago…my goodness…how time flies! Back then, most of the organic chemistry activity in the country was essentially single discipline, carried out in a few, well-endowed, elite universities, and led predominantly by men, with a significant proportion of them British or British-trained partly because Australian universities have only awarded PhD degrees since 1948 and only in significant numbers since the 1960s. 1 It wasn't until 1996 that the first female Associate Professor and Reader in Chemistry was appointed at the University of Melbourne!
N,N-dialkyl-N-chlorosulfonylchloroformamidines 1 reacted regioselectively with 4-hydroxy-2-pyrone... more N,N-dialkyl-N-chlorosulfonylchloroformamidines 1 reacted regioselectively with 4-hydroxy-2-pyrone derivatives 2 to give 3-dialkylamino-1,1,8-trioxo-1H-1λ 6-pyrano[3,4-e][1,4,3]oxathiazines 3. Dichloride 1b reacted regioselectively with 1,3-dimethylbarbituric acid 10 to give 3-diethylamino-5,7-dimethyl-1,1,6,8-tetraoxo-1H-1λ 6-pyrimido[5,4-e]-[1,4,3]oxathiazine 11. The compounds 3 and 11 are derivatives of new ring systems.
N,N-dialkyl-N-chlorosulfonylchloroformamidines 1 reacted regioselectively with 4-hydroxy-2-pyrone... more N,N-dialkyl-N-chlorosulfonylchloroformamidines 1 reacted regioselectively with 4-hydroxy-2-pyrone derivatives 2 to give 3-dialkylamino-1,1,8-trioxo-1H-1λ 6-pyrano[3,4-e][1,4,3]oxathiazines 3. Dichloride 1b reacted regioselectively with 1,3-dimethylbarbituric acid 10 to give 3-diethylamino-5,7-dimethyl-1,1,6,8-tetraoxo-1H-1λ 6-pyrimido[5,4-e]-[1,4,3]oxathiazine 11. The compounds 3 and 11 are derivatives of new ring systems.
N,N-dialkyl-N-chlorosulfonylchloroformamidines 1 reacted regioselectively with 4-hydroxy-2-pyrone... more N,N-dialkyl-N-chlorosulfonylchloroformamidines 1 reacted regioselectively with 4-hydroxy-2-pyrone derivatives 2 to give 3-dialkylamino-1,1,8-trioxo-1H-1λ 6-pyrano[3,4-e][1,4,3]oxathiazines 3. Dichloride 1b reacted regioselectively with 1,3-dimethylbarbituric acid 10 to give 3-diethylamino-5,7-dimethyl-1,1,6,8-tetraoxo-1H-1λ 6-pyrimido[5,4-e]-[1,4,3]oxathiazine 11. The compounds 3 and 11 are derivatives of new ring systems.
N-aryl methylene benzo-fused sultams (2,3-dihydrobenzo[d]isothiazole 1,1-dioxides) underwent [3þ2... more N-aryl methylene benzo-fused sultams (2,3-dihydrobenzo[d]isothiazole 1,1-dioxides) underwent [3þ2] cycloaddition with benzonitrile oxide to give 5-spiro isoxazoline adducts with complete regioselectivity. Steric hindrance by atropisomerism around the N-aryl bond induced facial selectivity in these cycloadditions.
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