Reactions of heterocumulenes with organometallic reagents: XVII. One-pot synthesis of alkoxy and (alkylsulfanyl)-substituted pyrroles and 2,3-dihydropyridines from aliphatic isothiocyanates and lithiated alkoxyallenes |
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Authors: | N A Nedolya L Brandsma O A Tarasova A I Albanov B A Trofimov |
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Institution: | 1.Faworsky Irkutsk Institute bof Chemistry, Siberian Branch,Russian Academy of Sciences,Irkutsk,Russia;2.Utrecht University,Utrecht,Netherlands |
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Abstract: | A fundamentally new approach was developed to designing pyrrole and dihydropyridine rings from available allenes and isothiocyanates
involving a single preparative stage. Applying the reaction of lithiated alkoxyallenes with aliphatic isothiocyanates we have
synthesized previously unknown 1-alkyl(cycloalkyl) pyrroles and 2,3-dihydropyridines with rare alkoxy- and alkylsulfanyl substituents.
It was proved that the five- and six-membered azaheterocycles formed as a result of competing reactions of direct intramolecular
cyclization of S-alkylated adducts of lithiated alkoxyallenes with isothiocyanates (1-aza-1,3,4-trienes) into pyrroles and
of 1,5]-sigmatropic rearrangement into conjugated 2-aza-1,3,5-trienes with subsequent closure into dihydropyridine ring (through
6π-electrocyclization). |
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