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Ring transformations of heterocyclic compounds. XIX . Spiro[dihydropyridine‐indolines] novel heterocycles with two spiro ‐condensed N ‐containing subunits easy accessible by 1,3‐oxazinium ring transformation
Author(s) -
Zimmermann Thomas,
Abram Ulrich
Publication year - 2000
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.5570370535
Subject(s) - chemistry , ring (chemistry) , dihydropyridine , acetonitrile , indoline , triethylamine , tetrafluoroborate , stereochemistry , transformation (genetics) , carbazole , medicinal chemistry , organic chemistry , catalysis , calcium , biochemistry , ionic liquid , gene
The synthesis of hitherto unknown 1‐benzoyl‐1′,3′,3′‐trimethyl‐4,6‐diphenylspiro[1,2‐dihydropyridine‐2,2′‐indolines] 5 from 2,4,6‐triphenyl‐1,3‐oxazinium tetrafluoroborate ( 1b ) and 1,3,3‐trimethyl‐2‐methyleneindolines 2 (used as such or generated in situ from the corresponding 3 H ‐indolium salts 4 ) in the presence of triethylamine in anhydrous acetonitrile by a 3,6‐[C 3 N+C 2 ] 1,3‐oxazinium ring transformation is reported. Structure elucidation is performed by an X‐ray structure determination of the spiro[dihydropyridine‐indoline] 5a . Spectroscopic data of the transformation products and their mode of formation are discussed.