2,5-bis-(2-n-lower alkyl amino isopropyl)-1,3,4-trithiolanes and process for the preparation thereof

Abstract

Abstract DIMERCAPTO COMPOUNDS CHARACETERIZED AS ALPHA, ALPHADIMETHYL-BETA, BETA-DIMERCAPTO-N-LOWER ALKYL-(PHENYL AND SUBSTITUTED PHENYL) ETHYLAMINES OF THE STRUCTURAL FORMULA: R-C(-SH)2-C(-CH3)2-NH-R1 (I) WHERE R IS PHENYL AND SUBSTITUTED PHENYL AND R1 IS LOWER ALKYL CONTAINING 1 TO 8 CARBON ATOMS ARE DESCRIBED. TRITHIOLANE CONDENSATION DERIVATIVES OF THE DIMERCAPTO COMPOUNDS (I) PREPARED BY OXIDATION WITH THE ELIMINATION OF HYDROGEN SULFIDE ARE ALSO DESCRIBED. THE DIMERCAPTO COMPOUNDS (I) ARE GENERALLY PREPARED BY REACTING AN ALPHA, ALPHA-DIMETHYL-BETA-N-LOWER ALKYL IMINE-(PHENYL AND SUBSTITUTED PHENYL) ETHYLAMINE OF THE STRUCTURAL FORMULA: R-N(=N-R2)-C(-CH3)2-NH-R1 (III) WHERE R AND R1 ARE AS IN THE DIMERCAPTO COMPOUNDS (I) AND R2 IS A LOWER ALKYL GROUP CONTAINING 1 TO 8 CARBON ATOMS WITH HYDROGEN SULFIDE IN AN INERT ANHYDROUS POLAR ORGANIC SOLVENT FOR THE IMINO COMPOUNDS (III) AT TEMPERATURES LESS THAN THE DECOMPOSITION TEMPERATURE OF THE DIMERCAPTO COMPOUNDS (I) AND UNTIL (I) IS FORMED AND PRECIPITATES FROM THE REACTION MIXTURE. THE IMINO COMPOUNDS (III) ARE PREFERABLY PREPARED BY REACTING A COMPOUND OF THE STRUCTURAL FORMULA: R-CO-C(-CH3)2-NH-R1 (II) WITH A LOWER ALKYL AMINE (R2-NH2) CONTAINING 1 TO 8 CARBON ATOMS. THE PRODUCT DIMERCAPTO COMPOUNDS (I) AND TRIHIOLANES ARE PARTICULARLY USEFUL AS ANTIMALARIALS IN MAMMALS.

Inventors

• 👤 Arthur B Ash
• 👤 Calvin L Stevens
• 👤 Anica Markovac

Bibliographic Details