Ms. Shvartsberg et al., A NEW HETEROCYCLIZATION IN THE SERIES OF ACETYLENIC DERIVATIVES OF ANTHRAQUINONE, Russian chemical bulletin, 45(7), 1996, pp. 1714-1719
2-Alkynyl-1-amino-9, 10-anthraquinones react with HNO2 in a mixture of
dilute HCl and dioxane at 20 degrees C to give 1,1-dichloronlkyl-1 H-
3-naphtho[2,3-g]indazole-6, 11-diones. This reaction differs from the
known cyclization of ortho-alkynylbenzenediazonium salts involving the
formation of a pyridazine ring (the Richter synthesis of 4-hydroxy- a
nd 4-halocinnolines).