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Chemical Interactions of Thiosemicarbazides with 1,4‐Benzo‐ and 1,4‐Naphthoquinones
Author(s) -
Hassan Alla A.,
Ibrahim Yusria R.,
Semida Ashraf A.,
Mourad AboulFetouh E.
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419941006
Subject(s) - chemistry , chloranil , naphthoquinone , yield (engineering) , 1,4 naphthoquinone , derivative (finance) , medicinal chemistry , benzoquinone , quinone , stereochemistry , organic chemistry , materials science , economics , financial economics , metallurgy
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 .