A new asymmetric synthesis of (S)-dolaphenine and its heteroaromatic congeners utilizing (+)-2-hydroxy-3-pinanone and (-)-3-hydroxy-2-caranone as chiral auxiliaries was written by Irako, Naoko;Hamada, Yasumasa;Shioiri, Takayuki. And the article was included in Tetrahedron in 1995.Reference of 55661-33-1 This article mentions the following:
(+)-2-Hydroxy-3-pinanone and (-)-3-hydroxy-2-caranone were resp. converted to the corresponding Schiff bases derived from 2-thiazolemethanamine, 2-thiophenemethanamine, 2-furanmethanamine and benzyl amine. Alkylation of the Schiff base derivative of 2-thiazolemethanamine followed by removal of the chiral auxiliaries (+)-2-hydroxy-3-pinanone and (-)-3-hydroxy-2-caranone afforded (S)-α-(phenylmethyl)-2-thiazolemethanamine [i.e., (S)-dolaphenine] in optically pure form. The method was applied to the asym. synthesis of the dolaphenine analogs also. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Reference of 55661-33-1).
Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Reference of 55661-33-1
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica