By Joëlle Prunet
The sequence issues in Heterocyclic Chemistry provides severe stories on current and destiny traits within the examine of heterocyclic compounds. total the scope is to hide themes facing all parts inside of heterocyclic chemistry, either experimental and theoretical, of curiosity to the final heterocyclic chemistry group. The sequence contains subject comparable volumes edited by way of well known editors with contributions of specialists within the box. All chapters from subject matters in Heterocyclic Chemistry are released on-line First with a person DOI. In references, issues in Heterocyclic Chemistry is abbreviated as best Heterocycl Chem and mentioned as a journal.
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Extra info for Synthesis of Heterocycles by Metathesis Reactions
The initial product 22a underwent isomerisation to afford tricyclic pyrrole derivative 23a in 65% yield. This approach, however, is not general and 22b underwent isomerisation to afford the alternative enamine product 23b in 65% yield. t. 4 Synthesis of Benzofused 5-Ring Heteroaromatic Systems by RCM RCM has also been employed as a key step in the synthesis of benzofurans and indoles. For these targets, the metathesis step can be used to construct either (a) the C2–C3 linkage or (b) the benzenoid portion of the target (Scheme 12).
F. Bower SES aza-Baylis-Hillman > 60% Yield SES NH CO2Me allylbromide K2CO3 R1 N R1 CO2Me R1 i. t. or o microwave 100 C MeO2C 17 >95% Yield 16 (SES = 2-trimethylsilylethylsulfonyl) SES N 18 ii. t-BuOK, DMF Br Ph H N H N MeO2C MeO2C 19a 78% Yield H N MeO2C 19b 59% Yield 19c 73% Yield Scheme 9 Aza-Baylis–Hillman-enabled RCM approach to pyrroles ii. NaHMDS ClP(O)(OPh)2 acylation R1 O O i. RCM R1 O 20 Ph O OP(O)(OPh)2 76-89% Yield O MeO ii. 3 Synthesis of Furans and Pyrroles by RCM–Isomerisation Sequences A final option for achieving aromatisation is to exploit strategies that rely upon isomerisation.
Scheme 18a). g. 112a, b) were accessed, but other substitution patterns could not be achieved, due to casespecific limitations associated with each step of the sequence. A more flexible CM-based pyridine methodology, which relies on late-stage introduction of nitrogen, has also been developed by the Donohoe group . Here, a CM-based approach was used to access α,β-unsaturated 1,5-dicarbonyl compounds 113. These were either modified further or condensed directly with an ammonia source to afford pyridines (Scheme 30).
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