Chemical Interactions of Thiosemicarbazides with 1,4‐Benzo‐ and 1,4‐Naphthoquinones

Abstract

Abstract Thiosemicarbazones 2a–e form charge‐transfer (CT) complexes with chloranil (CHL), fluoranil (TFQ) and 2,3‐dicyano‐1,4‐naphthoquinone (DCNQ). The donors 2a–d react with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) to yield 3‐amino‐5‐arylthiadiazoles 7 and DDQ‐H 2 ( 8 ). The thiosemicarbazide itself interacts with CHL via CT complexation to form the products 10–13 . Heating of thiosemicarbazide ( 1 ) with 2,3‐dichloro‐1,4‐naphthoquinone (DCHNQ) affords the thiadiazine derivative 15 .