Benz indazole

CHLOROPHENYL)AMINO)-4,5-DIHYDRO-N-(PHENYLMETHYL)-2H-BENZ( INDAZOLE-2-ACETAMIDE see CJR220... 

Benz. i lindazole. 970 Benz(/ indazol-.3-one, 1019 Benzl6 lindenol 1,2-c 1,4 diazepin-12-one. 1138... 

Benzimidazolo[l,2-c]thiatri azoles synthesis, 6, 612 Benz[cd]indazole antiaromaticity, 5, 208 Benz[cd]indazole, dihydroaromaticity, 5, 208 Benz[e]indolizine synthesis, 4, 466 Benzipiperylon biological activity, 5, 296 Benz[/]isoindoles synthesis, 4, 266... 

An elegant extension of these ring expansions involving diazidonaphthalenes has been reported. Early results on the photolysis of 1,8-diazidonaphthalene (14) indicated the formation of benz[t d]indazole (17).176 However, it has since been found that photolysis of the diazide in sodium methoxide-methanol/dioxane solution for a short period (20 -40 min) yields, in addition to the benz[c,d]indazole (17, 40%), a mixture of 9-azido-l-methoxy-5//-2-benzazepine (15 15-20%) and l,10-dimethoxy-5,5a-dihydroazepino[3,4-c]azepine (16 10-15%).117... 

Similar reactions of been described leading to benz[e]imidazoles, benz[g]indazoles, and benz[f]isoquinolines. 

The present review is comprehensive Chemical Abstracts has been searched by indexes up to mid 1981 and by a computer on-line substructure search up to Issue 26 of Volume 96. A few more recent references are included directly from the commoner international journals. This review covers 3//-pyrazoles that have been isolated or characterized spectroscopically, although some examples that are only transient intermediates in rearrangement reactions are also mentioned. Compounds having exocyclic double bonds and the benz-fused derivatives, the 3//-indazoles, are considered to be outside its scope. 

The acid-base properties of 4-nitroso-5-aminopyrazoles 50 have been studied. In particular, protonation sites have been determined where salts 51 are formed [66], The effects produced on II, 13C, and 15N chemical shifts by protonation and by hydrogen-bonding solvents on five azoles (imidazole, 4,5-dimethylimidazole, pyra-zole, 3,5-dimethyl-pyrazole, and 4,5-dihydro-3-methyl-2//-benz[g]indazole) have been determined experimentally. Phase effects on the 13C chemical shifts of the C-4 atom of pyrazole were discussed, based both on empirical models and on GIAO calculations of absolute shieldings in different complexes. The special case of the chemical shifts of pyrazoles in the solid state, where they form multiple N-H N hydrogen bonds, was also studied theoretically [88],... 

Benzimidoyl chloride, N-phenyl-, Friedel-Crafts benzoylation using, 55, 195 Benz[g]indazoles. 5-trifluoroacetyl-3-trifluoromethyl-, 60, 17 Benz[c]indole, 4.5,6,7,8,9-hexafiuoro-2-phenyl-, 59, 14... 

DIHYDRO-3-(PHENYLAMINO)-2H-BENZ(G)INDAZOL-2-YL)ACET-YL)MORPHOLINE... 

N-(((4-CHLOROPHENYL)AMINO)CARBON iT)-2,fi-DIFLUOROBENZAMIDE see CJV250 4-((3-((4-CHLOROPHENYL)ANnNO)-4,5-DIHYDRO-2H-BENZ(G)INDAZOL-2-YL)ACETYL)MORPHOLINE see CJR210... 

From a qualitative viewpoint there is no doubt that the compounds classified as aromatic in Section 4.04.1.1 (pyrazoles, indazoles, isoindazoles, pyrazolones, indazolones, mesoionic derivatives) indeed have aromatic properties to a greater or lesser extent. Dihy-drobenz[cd]indazole (115) is also formally an aromatic compound since it has an odd number of electron pairs (n =7). However, due to the presence of two adjacent nitrogen atoms the aromatic tautomer (115a) is not stable, and the compound exists as the 1,5- or 1,3-dihydro tautomers (115b) or (115c) <72JCS(P2)68). The antiaromatic benz[cd]indazole (116), although unstable, has been fully characterized by N, H and NMR spectroscopy... 

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