Synthesis of 2-Selenoxo-1,3-thiazolidin-4-ones and 2-Selenoxo-1,3-thiazinan-4-ones from Isoselenocyanates

2-Selenoxo-1,3-thiazolidin-4-ones (selenorhodanines) (7a-h) and 2-selenoxo-1,3-thiazinanes (8a-c) can easily be synthesized in a one-pot procedure from aryl isoselenocyanates and α- and β-mercapto carboxylic acids, respectively

First synthesis of a selenazepane

The firstsynthesis of perhydroselenazepane derivatives by the reaction of aryl isoselenocyanates with 5-chlorobutylamine in the presence of triethylamine in DMF as a one-pot procedure is described

Synthesis of 5-Selenoxo-1,2,4-triazole-1-carboxylates from Isoselenocyanates and Azodicarboxylates

A mixture of an azodicarboxylate and triphenylphosphine in dichloromethane reacted with aryl isoselenocyanates (1) at room temperature to give 4,5-dihydro-5-selenoxo-1H-1,2,4-triazole-1-carboxylates (4a-f) in a one-pot reaction in good to excellent yields. The isoselenocyanates (1) have been prepared conveniently from formamides by treatment with elemental selenium and phosgene according to Barton’s procedure

Selenium-containing heterocycles from isoselenocyanates: synthesis of 2-methylidene-1,3-selenazolidine derivatives

A convenient and unequivocal synthesis of the title compounds from isoselenocyanates, malononitrile or 2-cyanoacetate, and 1,2-dibromoethane or a-halogenated carboxylic acid derivatives is reported. The proposed reaction mechanism involves in situ cyclization of different halogenated compounds with an intermediate keten-N,Se-acetal, generated by the base promoted nucleophilic addition of the acidic cyanomethylenes to aliphatic and aromatic isoselenocyanates. Chemical and spectroscopic evidence for the structures of the new compounds is presented

Isoselenocyanates as building blocks for Selenium-containing heterocycles

Isoselenocyanates are conveniently accessible from elemental selenium in safe and efficient reactions. They can be used either as reactive intermediates or as relatively stable and storable starting materials for the preparation of selenaheterocycles or heterocyclic selones. In most cases, the reactions are initiated by a nucleophilic attack onto the isoselenocyanate, followed by a cyclization via the Se- or the N-atom. Alternatively, the intermediate adduct of the nucleophile and the isoselenocyanate can undergo a second nucleophilic addition with a third compound and subsequent cyclization