Abstract
Thioacetalization of the nitrobenzaldehydes with 2-mercaptoethanol is easily carried out in the presence of TMSCl and dichlorodimethylsilane without heating and using of additional solvent. The reaction direction is defined by the reagents ratio and led to formation of bis(2hydroxyethyl)dithioacetals (yield 76-91%) or 1,3-oxathiolanes (yield 76-91%). Bis(2-hydroxyethyl)dithioacetals are easily transformed in the corresponding 1,3oxathiolanes at long storage without heating or influence of catalysts, and also under electronic and chemical ionization.
Highlights
Nitro-substituted aromatic and heterocyclic compounds possess important biological activities[1] and are potential sources of the nitric oxide in living organisms.[2]
It is known that synthesis of the oxa- and thioacetals from carbonyl compounds proceeds via the catalysis with proton acids,[14,15] Lewis acids,[16,17,18,19,20] ets.[21,22]
In continuation of our study of catalytic activity of TMSCl and other organochlorosilanes in the acetalization reaction to synthesize nitroaromatic dithio- and oxathioacetals we have investigated for the first time the interaction of o, m, p – nitrobenzaldehydes with mercaptoethanol without heating in the presence of chlorometylsilanes
Summary
Nitro-substituted aromatic and heterocyclic compounds possess important biological activities[1] and are potential sources of the nitric oxide in living organisms.[2]. Using the interaction of 4-nitrobenzaldehyde with 2-mercaptoethanol as an example, we have studied the effect of the catalyst structure and amount, the reaction temperature, the organochlorine solvent nature and the reagents ratio on yields of the target products 2a and 3a (Table 1).
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