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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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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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Authors and Affiliations

  1. Faworsky Irkutsk Institute bof Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, 664033, Russia

    N. A. Nedolya, O. A. Tarasova, A. I. Albanov & B. A. Trofimov

  2. Utrecht University, Utrecht, Netherlands

    L. Brandsma

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  1. N. A. Nedolya
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Original Russian Text © N.A. Nedolya, L. Brandsma, O.A. Tarasova, A.I. Albanov, B.A. Trofimov, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 5, pp. 658–676.

For Communication XVI, see [1].

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Nedolya, N.A., Brandsma, L., Tarasova, O.A. et al. 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. Russ J Org Chem 47, 659–677 (2011). https://doi.org/10.1134/S1070428011050034

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