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Additionen von 2,2‐Dimethyl‐3‐dimethylamino‐2 H ‐azirin an 2‐Formyl‐cycloalkanone und Sulfinsäuren
Author(s) -
Chandrasekhar B. Parthasarathi,
Schmid Ursula,
Schmid Rudolf,
Heimgartner Heinz,
Schmid Hans
Publication year - 1975
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.19750580423
Subject(s) - chemistry , yield (engineering) , medicinal chemistry , adduct , benzene , azirine , salt (chemistry) , organic chemistry , ring (chemistry) , materials science , metallurgy
2,2‐Dimethyl‐3‐dimethylamino‐2 H ‐azirine ( 1 ) reacts with the formyl‐cycloalkanones 4 – 8 in boiling benzene to give the 1:1 adducts 13 – 17 in 60–99% yield (Table). These adducts are N′‐[(2‐oxo‐cycloalkylidene)‐methyl] derivatives of 2‐amino‐N, N‐dimethylisobutyramide. The reaction mechanism (Scheme 6) is analogous to the mechanism of the reaction of 1 with carboxylic acids and cyclic enolisable 1,3‐diketones [1]. Sulfinic acids and 1 undergo a similar reaction at −15° to yield 2‐sulfinamido‐N, N‐dimethylisobutyramides (Schemes 4 and 7), while sulfonic acids and the azirine 1 lead to a dimeric salt of type 20 , which with sodium hydroxide gives the dihydropyrazine 21 (Scheme 5).