Premium
Novel sultones. II. 1,4‐dialkyl‐9‐oxo‐9 H ‐indeno [1,2‐ d ] [1,2] oxathiin 3,3‐dioxides
Author(s) -
Paull Kenneth D.,
Cheng C. C.
Publication year - 1974
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.5570110632
Subject(s) - chemistry , reagent , pyridine , sulfuric acid , hydrazine (antidepressant) , halogenation , derivative (finance) , salt (chemistry) , medicinal chemistry , organic chemistry , chromatography , financial economics , economics
A new type of sultone, 1,4‐dialkyl‐9‐oxo‐9 H ‐indeno[1,2‐ d ] [1,2]oxathiin 3,3‐dioxides, can be readily synthesized by treating 3 hydroxy‐3‐phenylalkanoic acid with a mixture of acid anhydride and sulfuric acid. A mechanism for the formation of these sultones is proposed. A postulated intermediate in the preparation of the 1,4‐dimethyl analog, 3‐ethylideneindan‐1‐one, was prepared and subsequently converted to the same 1,4‐dimethyl compound by the same reagents. Bromination of these sultones gave the I‐bromalkyl derivatives while treatment with hydrazine yielded pyrazolium sulfonates. Under different reaction conditions, 3‐ethylidene‐indan‐1‐one formed a pyrylium salt, which, in turn, was converted to a fused tricyclic pyridine derivative with ammonia.