700874-12-0

Upstream product

• 918135-78-1 methyl N-isopropyl-2-methoxybuta-2,3-dienimidothioate 
• 2253-73-8 isopropyl isothiocyanate 
• 13169-00-1 Methoxyallene 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

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

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.

Application of copper catalysis in a one-pot procedure for 1-alkyl-3- methoxy-2-methylthiopyrroles starting from methoxyallene and alkyl isothiocyanates

1-Alkyl-3-methoxy-2-methylthiopyrroles are obtained with high purities and in high yields by Cu(I)halide-catalyzed cyclization of the products from addition of 1-lithiomethoxyallene to alkyl isothiocyanates and subsequent methylation.

Further Developments in the Reaction of 2-Aza-1,3,5-trienes with Superbases: Competitive Formation of New 4,5-Dihydro-1,3-thiazoles, Dihydroazepines, and Azepines by Tandem Deprotonation-Cyclization

Allyl- and benzylsulfanyl-substituted 2-aza-1,3,5-trienes, which are readily available from alkoxyallenes, isothiocyanates, and allyl or benzyl bromide, are easily transformed into polyfunctionalized 4,5-dihydro-1,3-thiazoles (2-thiazolines) through depro

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

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

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.

Mass spectra of new heterocycles: X. Fragmentation of the molecular ions of 1-alkyl(cycloalkyl, aryl)-3-alkoxy(aryl)-2-methylsulfanyl-1H-pyrroles

The mass spectra of previously unknown 1-alkyl(cycloalkyl, aryl)-3-alkoxy(aryl)-2-methylsulfanyl-1H-pyrroles were studied. Fragmentation of all 3-alkoxy-substituted pyrroles under electron impact (70 eV) follow both ether and sulfide decomposition paths;

Allenic compounds and isothiocyanates as key building units in the synthesis of heterocycles

Reaction between lithiated allenic compounds and isothiocyanates, R 1N=C=S, in most cases gives exclusively thioimidates with the allenic structure, C=C=CC(SLi)=NR1. These intermediates have been used in novel approaches to 2,3-dihydropyridines, pyrroles, quinolines, cyclobutanopyrrolines, and thiophene or dihydrothiophene derivatives. The procedures leading to the heterocycles with a nitrogen atom in the ring involve S-alkylation followed by simple heating or by treatment with copper(I) halide. 2-Aminothiophenes and 2-imino-2,5-dihydrothiophenes are formed by intramolecular nucleophilic attack of the thiolate moiety on the allenic system and subsequent addition of methyl iodide or protonation.