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Cycloadditionen mit Azabenzolen, XIII. Reaktionen von 1,2,4,5‐Tetrazinen mit Fulvenen
Author(s) -
Und Michael Bachmann,
Neunhoeffer Hans
Publication year - 1979
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.197919790511
Subject(s) - chemistry , pyridazine , cycloaddition , tetrazine , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Cycloaddition Reactions with Azabenzenes, XIII. ‐ Reactions of 1,2.4,5‐Tetrazines with Fulvenes Depending on the conditions, reaction of 6‐dialkylaminofulvenes 1 with 3,6‐diphenyl‐1,2,4,5‐tetrazine ( 2a ) affords 5‐dialkylaminomethylene‐1,4‐diphenyl‐5H‐cyclopenta[ d ]pyridazines 10a‐d , 3,6‐diphenylpyridazine ( 12 ), 4‐(2‐dimethylaminovinyl)‐3,6‐diphenylpyridazine ( 13 ), 9‐dimethylaminomethylene‐ 1,4,5,8‐tetraphenyl‐4a,4b,8a,9a‐ tetrahydro‐9 H ‐cyclopenta[1,2‐ d :3,4‐ d ]dipyridazine ( 14 ), and 9‐dimethylaminomethylene‐1,4,5,8‐tetraphenyl ‐9 H ‐cyclopenta‐[1,2‐ d :3,4‐ d ]dipyridazine ( 15 ). Compounds 10a and 10b are easily hydrolyzed, yielding 1,4‐diphenyl‐2‐ H ‐cyclopenta[d]pyridazine‐5‐carbaldehyde ( 11a ) and 1‐(1,4‐diphenyl‐2‐ H ‐cyclopenta[ d ]pyridazine‐5‐yl)ethanone ( 11b ), respectively. The structures of compounds 10 and 12‐15 were determined by spectroscopic methods, chemical reactions or synthesis by an independent route.