N-(Heteroaromatic-Substituted Methyl) Derivatives of 2-Aminoethanethiol ^1,2

Journal Article · Sun Jul 01 04:00:00 EDT 1962 · Journal of Organic Chemistry

DOI:https://doi.org/10.1021/jo01054a039· OSTI ID:4693986

Johnston, Thomas P.; Gallagher, Anne

Several methods for the preparation of N-(heteroaromatic-substituted methyl) derivatives of 2-aminoethanethiol were investigated. The sodium borohydride reduction of Schiff bases derivable from cystamine and heteroaromatic aldehydes (for example, Ia and Ib) may have general utility, for the preparation of this type of N-substituted 2aminoethanethiol. The iodine oxidation of the thiaolidines IIa and IIb was demonstrated to be an advantageous source of the corresponding Schiff bases. The direct aralkylation of cystamine with 8- (bromomethyl)quinoline was shown to be controllable so as to give as the predominant product either a tetra- or a disubstituted cystamine (IX and X, respectively). Sulfur cleavage of the disubstituted cystamines VIa and X afforded the corresponding intra Bunte salts.

• Research Organization: Southern Research Inst., Birmingham, Ala.
• Sponsoring Organization: USDOE
• NSA Number: NSA-17-021728
• OSTI ID: 4693986
• Journal Information: Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 7 Vol. 27; ISSN 0022-3263
• Country of Publication: Country unknown/Code not available
• Language: English

Related Subjects

BOROHYDRIDES
BORON HYDRIDES
CHEMISTRY
CYSTAMINE
ORGANIC SULFUR COMPOUNDS
PREPARATION
SODIUM COMPOUNDS