Synthesis of 5-aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinoline derivatives from 3-cyanopyridine-2(1H)-thiones and 2-(chloromethyl)benzamide

• Published in: Russian chemical bulletin Vol. 67; no. 8; pp. 1492 - 1499
• Main Authors: Kalugin, V. E., Shestopalov, A. M.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.08.2018; Springer Nature B.V
• Subjects: Benzamide; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Condensates; Inorganic Chemistry; Organic Chemistry; Oxidation; Potassium; Substitutes; Sulfones; isoquinolines; potassium; thiones; 2-(chloromethyl)benzamides; 3-cyanopyridine-2; butoxide; 11-dioxides; isoquinoline 11-oxides; domino reactions; 5-aminopyrido[3′,2′:4,5]thieno [3,2; isoquinoline 11; 5-aminopyrido[ 3′,2′:4,5]thieno[3,2; 5-aminopyrido[3′,2′:4,5]thieno[3,2
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-018-2245-x

Substituted 5-aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinolines were synthesized by condensation of substituted 3-cyanopyridine-2(1 H )-thiones with 2-(chloromethyl)benzamide and subsequent treatment of the condensation products with potassium tert -butoxide. Oxidation of the condensation products to sulfoxides and sulfones followed by treatment of these compounds with potassium tert -butoxide gives substituted 5-aminopyrido[3′,2′:4,5]thieno[3,2- c ]isoquinoline 11-oxides and substituted 5-aminopyrido[3′,2′:4,5]thieno[3,2- c ]isoquinoline 11,11-dioxides in good yields.