By Alan R. Katritzky
The definitive serial within the box — because 1960.* offers up to date fabric on a quick growing to be and hugely topical topic sector* includes the most recent examine protecting a large choice of heterocyclic subject matters* Written through major professionals and designed as a instruction manual for college students and and educational researchers
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Additional resources for Advances in Heterocyclic Chemistry, Vol. 96
Tymoshenko The pyrrole derivative of carbonyl azide 206 undergoes thermal Curtius rearrangement into isocyanate, which spontaneously cyclizes into pyrrolodiazepinone 207 (Equation (27) (1991JHC1911)). CON3 AcOH N N 62% NH (27) O 206 207 Ketoester 208 derived from 1-(2-nitrophenyl)-1H-pyrrole and ethyl oxalyl chloride can be selectively reduced at the keto group with zinc iodide and sodium cyanoborohydride. Further reduction of the nitro group and cyclization to lactam 209 has been accomplished by treatment with stannous chloride in refluxing ethanol (Scheme 43 (2003BMCL2195)).
Sequential Mannich reaction of ester 210a or nitrile 210b, alkylation and displacement of quaternary ammonium salt affords azides 211. Further hydrogenation can be followed by intramolecular cyclization under basic conditions into pyrrolo-benzodiazepinone 212 (Scheme 44 (1994JHC1317, 1994S164)). Aminomethyl substituted pyrrolo-benzdiazepine can be formed from the Cbz-protected precursor 214 and further reduced into tetrahydro derivative 215. Alternatively, the unsubstituted ring in 217 has been synthesized by a Bischler– Napieralski method (Scheme 45 (1993JHC749).
These processes lead under mild conditions to cyclization products 152. The high regioselectivity can be explained by the formation of dipolar intermediate 151 favored by the predominant enolization of the carbonyl adjacent to phenyl ring. Terminal alkynes react in the similar fashion, although, in this case, mixtures of regioisomers have been reported due to steric hindrance in the intermediate enol (Scheme 30 (1993JOC4885)). The next two examples illustrate intramolecular oxepine C–C bond formation of the furan precursors.