Indazole dione

Chemical Name 21-ester of 1(1-benzyl-1 H-indazol-3-yl-oxy]-acetic acid with 11/3,17a, tri-hydroxy-pregn-4-ene 3 0-dione... 

CN (llp)-l l,17-dihydroxy-21-[[[[l-(phenylmethyl)-lH-indazol-3-yl]oxy]acetyl]oxy]pregn-4-ene-3,20-dione... 

Dumitrascu and co-workers (52) transformed 4-halosydnones into 5-halopyr-azoles by cycloaddition with DMAD and methyl propiolate followed by retro-Diels-Alder loss of CO2. Turnbull and co-workers (194) reported that the cycloadditions of 3-phenylsydnone with DMAD and diethyl acetylenedicarboxylate to form pyrazoles can be achieved in supercritical carbon dioxide. Nan ya et al. (195) studied this sydnone in its reaction with 2-methylbenzoquinone to afford the expected isomeric indazole-4,7-diones. Interestingly, Sasaki et al. (196) found that 3-phenylsydnone effects the conversion of l,4-dihydronaphthalene-l,4-imines to isoindoles, presumably by consecutive loss of carbon dioxide and A-phenylpyrazole from the primary cycloadduct. Ranganathan et al. (197-199) studied dipolar cycloadditions with the sydnone 298 derived from A-nitrosoproline (Scheme 10.43). Both acetylenic and olefinic dipolarophiles react with 298. In... 

When the Knoevenagel adducts formed from aldehydes with dimedone were reacted with dihydropyridazine-dione 156 (Scheme 30), pyridazino indazole triones 157 were obtained under solvent-free conditions in moderate yields [67]. The compounds were tested for their antibacterial properties against E. coli (ATCC 25922), P aeruginusa (ATCC 85327), Bacillus subtilis (ATCC 465) and S. aureus (ATCC 25923) (Table 11). Compounds 158-160 were found to be more active than Amoxicillin against E. coli but less potent than Norfloxacin. None of the reported compounds was active against S. aureus. 

There are only a few derivatives of the indazole-6,7-dione 178 and 4,5-dione all other indazolequinones belong to the 4,7-dione system 179. 

Similarly, alkane- and arenesulfonyl isocyanates gave 2-sulfonyl-2,3-dihydroisoindol-l-ones 11 with benzocyclopropene. 2,3-Dihydroisoindol-l-one was produced as a byproduct in 4% yield in the case of arenesulfonyl isocyanates. Cyclopropa[ ]naphthalene underwent addition to 4-phenyl-47/-l,2,4-triazole-3,5-dione at 20°C almost instantaneously to give an indazole 12 in 92% yield.Both reactions are believed to occur by electrophilic attack on the cyclo-proparene and may involve a zwittcrionic intermediate. When benzyne was generated from benzenediazonium-2-carboxylate in refluxing dioxane in the presence of cyclopropa[Z ]naph-thalenc, 5//-naphtho[2,5-a]indene was formed in 13% yield. 

Pyridazino l,6-6 indazole, 768 lS ridazino[4.3-6 indoie, 1024 l ridazino 6,l-o isoindole, 1055 F ridazino l,2-6 phthalazine-6,l l-dione,... 

Cyclization of azobenzene and its derivatives tends only to occur under acid conditions. The reaction of the conjugate acids of azobenzene with anhydrous aluminium chloride, stannic chloride, and ferric chloride in 1,2-dichIoroethane has now been reported in detail.144 Benzo[c]cinnoline is formed, but the production of benzidine suggests that the reaction involves photodisproportionation. Similar cyclization is observed with the conjugate acids of azobenzenedicar-boxylic acids.145 With these compounds the reaction also occurs in 98% sulphuric acid to yield, from the 2,2 -isomer, benzo[c]cinnoline-4,7-dicarboxylic acid (90) and indazolo[2,1 - ]indazole-6,12-dione (91) in equal amounts the 3,3 -and 4,4/-dicarboxylic acids of azobenzene likewise give the corresponding cinnolines.145 It is important to note here that benzo[c]cinnoline is light-labile in 148... 

In 2004, the synthesis of indazolo[2,l-a]indazole-6,12-diones was carried out by a rhodium-catalyzed cyclocarbonylation of azobenzenes by the group of... 

C14H16N2O3 0.5 H2O, 2,3a,4,5-Tetrahydro-7,8-dimethoxy-3a-methyl-3H-benz[g]indazol-3-one hemihydrate, 46B, 272 Cl4H16N2O4, 2,3-Hydroxy-2,3-dimethyl-4a,9a-diaza-1,2,3,4,4a,9,9a,10-octahydroanthracene-9,10-dione, 44B, 256 Cl4H16N2O5 f 1,2/3-Dimethoxycarbonyl-3aa-hydroxy-2a,3,3,8,8aa-penta-hydropyrrolo[2,3-b]indole, 44B, 256 C14H1yBrjN, trans-6,8-Dibromo-1,2,3,4,4a,9a-hexahydro-4a,9-dimethyl-carbazole, 37B, 146... 

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