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Derivatives from Isoselenocyanates: Synthesis of 2‐Phenyl‐6 H ‐[5,1,3]benzoselenadiazocine
Author(s) -
Atanassov Plamen K.,
Linden Anthony,
Heimgartner Heinz
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490132
Subject(s) - chemistry , diethyl malonate , acetone , sulfur , salt (chemistry) , medicinal chemistry , base (topology) , malonate , stereochemistry , organic chemistry , catalysis , mathematical analysis , mathematics
Abstract The reaction of N‐ phenylbenzimidoyl isoselenocyanates 8 with primary and secondary amines in acetone at room temperature, followed by treatment with a base, led to 6 H ‐[5,1,3]benzoselenadiazocine derivatives of type 10 ( Scheme 3 ). An analogous cyclization was observed when 8a and 8b were reacted with the Na salt of diethyl malonate in EtOH at room temperature, which yielded the eight‐membered selenaheterocycles 11 ( Scheme 5 ). The molecular structures of some of the products, as well as that of a sulfur analogue, have been established by X‐ray crystallography ( Figs. 1 – 4 ). The isoselenocyanates 8 have been prepared from N ‐(2‐methylphenyl)benzamides 5 in a three‐step procedure via the corresponding imidoyl chlorides 6 , side‐chain chlorination to give 7 , and treatment with KSeCN ( Scheme 2 ).