By Gordon W. Gribble and Thomas L. Gilchrist (Eds.)
This quantity of growth in Heterocyclic Chemistry (PHC) is the fourteenth annual evaluation of the literature, masking the paintings released on vital heterocyclic ring platforms in the course of 2001. during this quantity there are really expert experiences. the 1st, through Jan Bergman and Tomasz Janosik, covers their paintings on sulfur-containing indoles. the second one, via David Knight, discusses five- endo -trig iodocyclisations. the next chapters, prepared through expanding heterocycle ring dimension, overview fresh advances within the box of heterocyclic chemistry with emphasis on synthesis and reactions.
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Extra info for A Critical Review of the 2001 Literature Preceded by Two Chapter on Current Heterocyclic Topics
A problem associated with such initial products 211 is their inherent instability; oxidation to the S,S-dioxide was carried out prior to characterization. As yet, the stereochemical characteristics of such cyclizations remain unknown. An isolated example 213 suggests that such cyclizations could be viable when the Electrophile-mduced 5-Endo Cyclizations 43 two reacting functions are attached to a ring 212 <94JOC5858>. Perhaps surprisingly, the cyclization is not stereoselective but interestingly does demonstrate that a thioacetal can be the source of the sulfur nucleophile without affecting the second thioether function.
21 Electrophile-induced 5-Endo Cyclizations aq. MeCN HO HO I 12, NaHCO3 I 9 Et'" 12 13[-5%] 14 15 ~"OH I E ! OH HO Et---~-~ HO 16 12' NaHC03 DRY MeCN 12 Et"' 13 [> 9 5 % 1 Almost inevitably, few discoveries are entirely novel. In 1978, Bartlett and Myerson <78JA3950> had observed a similar phenomenon when attempting to iodolactonize the hydroxy-ester 17. While the major product was indeed the expected butyrolactone 18 arising from ester dealkylation and 5-exo-trig cyclization, a minor product was the iodotetrahydrofuran 19, despite the fact that its formation required demethylation of the methyl ether.
Low temperatures are essential in this case. The related 2-thienyl derivative 150 may be more suitable for the latter transformation into a hydroxy group following, in this case, radical generation and trapping using allyl bromide. , PhSeCI Ph 146 ~" "0 ~ -Ph Ph 147 R =OTIPS [3:1] NHPh [3:1] SPh [3:1] SO2Ph [-9:1] 148 150 149 OH [3:7] OEt [1:9] OCHzCF 3 [1:3] OPh [1:4] Much the same pattern is observed when the substituent is a methoxycarbonyl group <99EJO9797>. Thus, selenocyclization of the erythro-[3-hydroxy-esters [151; R 1, R 2 - Me, Ph] gives largely (>9:1) the 2,5-trans-tetrahydrofurans 152 whereas similar reactions of the corresponding threo-isomers lead to the 2,5-cis isomers 153.
A Critical Review of the 2001 Literature Preceded by Two Chapter on Current Heterocyclic Topics by Gordon W. Gribble and Thomas L. Gilchrist (Eds.)