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A new intramolecular recyclization in water‐base cleavage reaction of 2,2‐dialkyl‐4‐hydroxymethylbenz[ f ]iso indolinium bromides and chlorides
Author(s) -
Chukhajian Emma O.,
Gevorkyan Hasmik R.,
Chukhajian Eliza O.,
Shahkhatuni Knarik G.,
Panosyan Henrik A.,
Tamazyan Rafael A.
Publication year - 2003
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570400614
Subject(s) - chemistry , intramolecular force , cleavage (geology) , medicinal chemistry , base (topology) , ammonium , stereochemistry , organic chemistry , mathematical analysis , geotechnical engineering , mathematics , fracture (geology) , engineering
The water‐base cleavage reaction of 2,2‐dialkyl‐4‐hydroxymethylbenz[ f ]isoindolinium bromides and chlorides (2b‐g) and (4a‐g) was investigated. It was established that the above‐mentioned salts in water‐base cleavage reaction undergo intramolecular recyclization. As a result 1,3‐dihydro‐4‐dialkylaminomethyl‐naphto[1,2‐ c ]furans (5a‐g) are obtained in 62‐72% yields. The same products in 65‐70% yields may be obtained by step cyclization cleavage reaction of dialkyl‐4‐hydroxybutyn‐2‐yl‐(3‐phenylpropargyl) ammonium salts (1b‐g) and (3a‐g) , as well. The structure of the resulting amines 5a‐g are determined and approved by X‐ray diffraction, nmr and ir spectroscopic methods.