Tetracyclines Communication 33. Synthesis of 8-chloro-5-methoxy-3,10-dioxo-1,2,3,4,4a,9,9a,10-octahydroanthracene [5-chloro-1,3,4,4a,9a,10-hexahydro-8-methoxy-2,9-anthracenedione]

Summary 8-Chloro-5-methoxy-3,10-dioxo-1,2,3,4,4a,9,9a,10-octahydroanthracene (Ib) was synthesized; this can serve as an intermediary in the preparation of the tetracyclic analog (IIb) of aureomycin,Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 806–810, May, 1965 Original article submitted April 22, 1963For preceding communication see [1],The authors thank L. B. Senyavina for infrared spectrum measurements.     

Properties of the amino group in N-(aminophenyl)pyridinium perchlorates

The pyridinium ring as a substituent in aniline is an electron acceptor, the effect of which is comparable to the effect of NO₂ and N(CH₃)₂ groups. Correlation of the reactivities with the basicities of the amino groups is not observed in the investigated reactions of N-(aminophenyl)pyridinium perchlorates with some electrophilic reagents, inasmuch as steric factors apparently play a greater role.