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Iminium carbonic acid derivative salts. IX . Synthesis of N,S ‐containing heterobicycles from N ‐protected 2‐methylthio‐1,3‐thiazinium and 2‐methylthiothiazolium salts part 1. Preparation of N ‐protected 2‐methylthio‐1,3‐thiazinium and 2‐methylthiothiazolium salts and their reaction with CH‐acidic compounds
Author(s) -
Hanefeld Wolfgang,
Naeeni Mahmoud,
Schlitzer Martin
Publication year - 1996
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.5570330639
Subject(s) - chemistry , ketene , iminium , tetrafluoroborate , yield (engineering) , derivative (finance) , medicinal chemistry , methyl iodide , salt (chemistry) , iodide , sodium hydride , organic chemistry , ion , catalysis , ionic liquid , materials science , economics , financial economics , metallurgy
N ‐Boc‐protected 1,3‐thiazine‐2‐thiones and thiazolidin‐2‐thiones were transformed into the corresponding 2‐methylthio‐1,3‐thiazinium and 2‐methylthiothiazolium salts by methyl iodide or trimethyloxonium tetrafluoroborate. This activated species were reacted with CH‐acidic compounds forming ketene‐ N,S ‐acetals. The protection group was removed with trifluoracetic acid to yield the N ‐unsubstituted ketene‐ N,S ‐acetals.