By Gordon W. Gribble and Thomas L. Gilchrist (Eds.)
This quantity of development in Heterocyclic Chemistry (PHC) is the fourteenth annual assessment of the literature, protecting the paintings released on very important heterocyclic ring platforms in the course of 2001. during this quantity there are really good stories. the 1st, by means of Jan Bergman and Tomasz Janosik, covers their paintings on sulfur-containing indoles. the second one, by means of David Knight, discusses five- endo -trig iodocyclisations. the following chapters, prepared through expanding heterocycle ring dimension, assessment fresh advances within the box of heterocyclic chemistry with emphasis on synthesis and reactions.
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Additional resources for A Critical Review of the 2001 Literature Preceded by Two Chapter on Current Heterocyclic Topics
Stereocontrol is good in more highly substituted examples <96G635>. 0 / - - ~ R-50~ PhSe+ 0 R[~~ePh OSePh N . N ~sePh,, 'R 202 t O-Alkenol hydroxylamines 203 can also participate in 5-endo-trig cyclizations without the complication of competing 4-exo reaction, in contrast to the benzylamines 192. However, in these cases, the electrophile was generated from phenylselenenyl persulfate and triflic acid and the cyclization carried out in methanol at 20~ <95TL163>. Only the trans product 204 was formed, although a more highly substituted example showcd poor stereoselectivity.
75-3h), less efficient (ca 70% vs >95%) and less selective in the case of the anti-isomers 98 than those using iodine <94TL7529>. In addition, and for the first time in our work, we isolated a small amounts (< 15%) of oxetanes arising from a competing 4-exo-trig pathway in some cases. Thus, in these examples at least, the use of NIS offers no advantages. These results contrast somewhat with those obtained from 5-endo cyclizations of 3alkene-l,2-diols, although the dissimilarities stem from the smaller size of hydroxy group relative to a methyl.
Knight 34 ether effect. Displacement by azide usually was the most efficient. Thus, exposure of iodotetrahydrofuran 27 to sodium azide in DMF at 80~ for 2h gave the inverted azide 121 in 87% isolated yield <99JCS(P1)2143>. Subsequent hydrogenation in the presence of Boc anhydride <89TL837> then delivered a good yield of the protected amine 122. Stronger heating gave substantial amounts of the elimination product, the 2,5-dihydrofuran 123. Displacement by an oxygen nucleophile could be effected using caesium acetate in hot DMF <81JOC4321> to give acetate 124 in moderate yield; the use of potassium superoxide and 18-crown-6 also in DMF <75CC658> gave marginally better yields of the corresponding alcohol, typically 60-70% at most.