918135-79-2Relevant academic research and scientific papers
Structural reorganization of (allyl-, benzyl-, and propargylsulfanyl)- substituted 2-aza-1,3,5-trienes in t-BuOK/THF/DMSO: Access to rare functionalized 2-thiazolines
Nedolya, Nina A.,Tarasova, Ol'Ga A.,Albanov, Alexander I.,Trofimov, Boris A.
, p. 2495 - 2498 (2014)
Treatment of (allyl-, benzyl-, and propargylsulfanyl)-substituted 2-aza-1,3,5-trienes, which are readily accessible from lithiated methoxyallene, isopropyl isothiocyanate, and allyl, benzyl, or propargyl bromide, respectively, with t-BuOK in THF/DMSO resu
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
Nedolya,Brandsma,Tarasova,Albanov,Trofimov
experimental part, p. 659 - 677 (2011/08/22)
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 fi veand 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 6p-electrocyclization). Pleiades Publishing, Ltd., 2011.
Simultaneous synthesis of 4,5-dihydro-3H-azepines and 3H-azepines, bearing alkoxy and alkylsulfanyl substituents, through metallation of 2-aza-1,3,5-trienes by t-BuOK
Nedolya, Nina A.,Tarasova, Ol'Ga A.,Volostnykh, Ol'Ga G.,Albanov, Alexander I.,Trofimov, Boris A.
experimental part, p. 3359 - 3368 (2011/10/09)
A new range of alkoxy- and alkylsulfanyl-substituted 4,5-dihydro-3H- azepines and 3H-azepines have simultaneously been obtained from conjugated 2-aza-1,3,5-trienes by treatment with t-BuOK under mild reaction conditions (THF/DMSO, ～-30 °C, 30 min). One-pot synthesis of 1-aza-1,3,4-trienes from α-lithiated alkoxyallenes, isopropyl isothiocyanate and alkyl iodides, followed by the thermally induced sigmatropic [1,5]-H shift, easily leads to starting 2-aza-1,3,5-trienes. The reaction proceeds via generation and [1,7]-electrocyclization of azatrienyl anions and represents a novel simple approach to both azacycloheptadienes and azacycloheptatrienes.
