A Critical Review of the 2001 Literature Preceded by Two by Gordon W. Gribble and Thomas L. Gilchrist (Eds.)

By Gordon W. Gribble and Thomas L. Gilchrist (Eds.)

This quantity of growth in Heterocyclic Chemistry (PHC) is the fourteenth annual overview of the literature, overlaying the paintings released on very important heterocyclic ring structures in the course of 2001. during this quantity there are really expert experiences. the 1st, by way 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 by means of expanding heterocycle ring measurement, assessment fresh advances within the box of heterocyclic chemistry with emphasis on synthesis and reactions.

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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.

34] using Wittig homologations <94CC2447>. Thus, treatment of the 2,5-trans-iodotetrahydrofurans 127 with triphenyltin hydride under standard conditions gave the radicals 128 which then underwent efficient cyclizations to give largely (ca. 1]heptanes 129 in excellent yields. Understandably, an analogue lacking the activating carbonyl in conjugation with the acceptor alkene function gave a lower but still respectable 59% yield of the derivative 130. Similarly, Barton-McCombie deoxygenation <75JCS(P1)1574> of the 2,5-cis-4- Electrophile-induced 5-Endo Qvclizations 35 hydroxytetrahydrofuran 131 gave very largely the 3-endo-5-exo isomer 132 in 77% isolated yield.

44 D. W. 6 2 225 5-ENDO-DIG CYCLIZATIONS 5-Endo-dig cyclizations are distinguished from the foregoing 5-endo-trig processes in two contrasting ways: firstly, these are favoured according to Baldwin's rules but, secondly, have enjoyed significantly less popularity. This surprising feature is despite early hints in the literature as to their viability. For example, mercuration of 3-alkyne-l,2-diols 226 under acidic conditions was reported to give good yields of 2,4-disubstituted furans 227 <55ZOB81; 77RZC249>.

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