Anthranils, nitro-, rearrangement

The yellow crystalline azaberbinone (388) has been prepared by several, closely related methods. Dehydrogenation of betaine 378 (Section III,E,2) with dichlorodicyanoquinone gives compound 388 directly. Alternatively, this compound (388) has been prepared in three ways from 6 -nitropapaverine (385) (Scheme 15) (i) Treatment of compound 385 with triethyl phosphite gives a low yield of betaine 388 directly (ii) compound 385 in methanolic KOH at reflux temperature gives the anthranil 386 which rearranges to the betaine 388 in hot triethyl phosphite and (iii) iodine oxidation of 6 -nitro-papaverine (385) generates the A-oxide 387 which is reduced to the betaine 388 by sodium bisulfite. The chemistry of compound 388 remains unexplored. 

Anthracene, 9,10-dihydro-9,9-dimethyl-as antidepressant, 1, 169 Anthracene, 1,4,5,8,9-pentamethyl-synthesis, 2, 537 Anthracyclinones synthesis, 1, 414, 4, 700 Anthramycin synthesis, 7, 614 Anthranil, 3-acyl-rearrangement, 5, 93 Anthranil, 3-aiyl-acridones from, 2, 93 thermolysis, 5, 91 Anthranil, 3-(imidazol-2-yl)-rearrangement, 5, 433 Anthranil, 6-nitro-reactions... 

Reinvestigation of the base-catalyzed rearrangement of o-nitrotoluene to anthranilic acid using lsO-enriched water has confirmed anthranil as a reaction intermediate.161 Anthranil is also suspected as being an intermediate in the gas-phase conversion of o-nitrotoluene to anthranilic acid.162 4-t-Butyl-7-methyl-6-nitro- and 6-t-butyl-5-methoxy-4-nitroanthranil are secondary photoproducts of 2-methoxy-4-methyl-3,5-dinitro-r-butylbenzene ( musk ambrette ) in methanolic sodium hydroxide.163... 

Nitro-3-(2,5-dimethoxyphenyl)anthranil rearranges to 1,4-dimethoxy-acridone, whereas the 6-nitro-3-(3,4-dimethoxyphenyl) derivative yields a mixture of rearranged and unrearranged dimethoxyacridones.165... 

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