Indeno indoles

Indeno-indolic compounds Chiral AGP, bovine serum albumin (BSA-DSC) and ovomucoid (Uliron ES-OVM) 12-34]... 

Indenopyrene, see Indeno[l,2,3-crf pyrene l//-Indole, see Indole Indolene, see Indoline Inexit, see Lindane Inhibisol, see 1,1,1-Trichloroethane Insecticide 497, see Dieldrin Insecticide 4049, see Malathion Insectophene, see a-Endosulfan, p-Endosulfan Intox 8, see Chlordane Inverton 245, see 2,4,5-T lodomethane, see Methyl iodide IP, see Indeno[l,2,3-crf pyrene IP3, see Isoamyl alcohol Ipaner, see 2,4-D IPE, see Isopropyl ether IPH, see Phenol Ipersan, see Trifluralin Iphanon, see Camphor Isceon 11, see Trichlorofluoromethane Isceon 122, see Dichlorodifluoromethane Iscobrome, see Methyl bromide Iscobrome D, see Ethylene dibromide Isoacetophorone, see Isophorone a-Isoamylene, see 3-Methyl-l-butene Isoamyl ethanoate, see Isoamyl acetate Isoamylhydride, see 2-Methylbutane Isoamylol, see Isoamyl alcohol Isobac, see 2,4-Dichlorophenol Isobenzofuran-l,3-dione, see Phthalic anhydride 1,3-Isobenzofurandione, see Phthalic anhydride IsoBuAc, see Isobutyl acetate IsoBuBz, see Isobutylbenzene Isobutane, see 2-Methylpropane Isobutanol, see Isobutyl alcohol Isobutene, see 2-Methylpropene Isobutenyl methyl ketone, see Mesityl oxide Isobutyl carbinol, see Isoamyl alcohol Isobutylene, see 2-Methylpropene Isobutylethylene, see 4-Methyl-l-pentene Isobutyl ketone, see Diisobutyl ketone Isobutyl methyl ketone, see 4-Methyl-2-pentanone Isobutyltrimethylmethane, see 2,2,4-Trimethylpentane Isocumene, see Propylbenzene Isocyanatomethane, see Methyl isocyanate Isocyanic acid, methyl ester, see Methyl isocyanate Isocyanic acid, methylphenylene ester, see 2,4-Toluene-diisocyanate... 

Developing their work on the use of microwave-assisted Niementowski reactions, the same group published the synthesis of novel triaza- and tetraaza-benzo a -indeno[l,2-c]anthracen-5ones by the condensation of anthranilic acid with 2-(2-aminophenyl)indole or benzimidazole (Scheme 3.49)78,79. 

The aromaticity obtained by means of the DE values and their differences in the single pseudoazulene systems are also the result of calculations of the bond orders (Fig. 1). The calculated bond alternations46 57-77-79-82-117118-129 are in line with the heteroaromaticity of the systems. Similar relationships were calculated for azulene.219 The extent of the bond alternation, however, differs from one system to the other (see Fig. 1). In indeno[2.1-f>]-l-benzo-pyran (44a) the bond lengths of the central cyclo[fo]pyran system indicate pronounced bond alternation, and in the opinion of the authors, the systems have little aromatic character.129 Calculations with 1 //-pyrindines (26) and 2//-pyrindines (29) show that 26 is more stable than 29, but both are less aromatic than indole.63 A comparison of SCF calculations for pseudoazulenes 26 and 29 with their aza analogs 68 and 69-73, which contain a pyrrole-type nitrogen, shows only minor perturbations of carbon-carbon bond lengths on replacing a =CH— moiety by =N—.66... 

To a solution of the S-(+)-4-acethoxy-9-[2-(5-ethyl-l,2,3,6-tetrahydro-pyridin-3yl)-l-(lH-indol-2-yl)-l-methoxycarbonyl-ethyl]-3a-ethyl-5-hydroxy-8-methoxy-6-methyl-3a,4,5,5a,6,ll,12,12b-octahydro-lH-6,12a-diaza-indeno[7,l-ca]fluorene-5-carboxylic acid methyl ester in dioxane and glacial acetic acid was added 37% aqueous formaldehyde and the mixture stirred at 35°C for 24 h. The solution was evaporated in vacuo and the residue suspended in chloroform and washed with cold aqueous 5% K2C03 solution. The chloroform layer was dried (MgS04), filtered, and evaporated. The residue was chromatographed eluting with EtOAc/MeOH, 10% NH4OH to give the product navelbine. 

The 5,6-dihydro-indeno[2,l-Z>]indole 19a is obtained by the photo-stimulated reaction of 16 with the enolate anion of 2-indanone in DMSO and in liquid ammonia (Sch. 22, n= 1) [92]. 

The palladium-catalyzed Sonogashira reaction between l-(2-propynyl)-l//-indole 1460 and l-iodo-2-(2-phenylethy-nyl)benzene 1461 was successful in producing 17/-indole 1462 in excellent yield (Scheme 279) <2005JOC6647>. Treatment of indole 1462 with a strong base produced 12-phenyl-7//-indeno[l, 2 4,5]pyrido[l,2- ]indole 1463 in... 

Synthesis of carbazoles and related indoles fused to carbocyclic rings is yet another fruitful field for application of the Fischer indolization, which has for example resulted in routes to indeno[2,l- ]indoles <20040M344>, diaryl-carbazoles <1999HC451>, tetrahydrocarbazole derivatives <2000JOC3387, 2003BMC3413, 1999CAL93,... 

Bos, M., Jenck, E., Martin, J. R., Moreau, J.-L., Sleight, A. J., Wichmann, J., Widmer, U. Novel agonists of 5HT2C receptors. Synthesis and biological evaluation of substituted 2-(indol-l-yl)-l-methylethylamines and 2-(indeno[l,2-h]pyrrol-l-yl)-l-methylethyl-amines. Improved therapeutics for obsessive compulsive disorder. 7. Med. Chem. 1997,40,2762-2769. 

Brown, Eastwood, and colleagues pyrolyzed qui-nolone-3,4-dicarboxylic anhydrides to give fused indoles (Scheme 3, equations 1 and 2) [14]. The unstable indeno[l,2-b]indole (1) reacted with various nucleophiles in low yield (17%-29%) (equation 3). 

An efficient three-component domino strategy for the synthesis of multi-functionahzed tetracyclic indeno[l,2-h]indole derivatives has again been reported by Tu, li, and coworkers [62]. The domino reaction between enaminones 57 and 2,2-dihydroxyindene-l,3-dione 105 in acid anhydride generated the fused pyrazoles 106 (tetracyclic 6-5-S-6 skeleton), which involved a nucleophilic substitu-tion/cychzation/methyl migration/aromatization/esterification. On the other hand,... 

Scheme 12.41 Selective synthesis of tetracyclic indeno[l, 2-b]indoles.

Li and Tu have described an innovative three-component domino reaction for the synthesis of multifunctionalized tetracyclic indeno[l,2-h]indole derivatives (Scheme 6.30) [59]. Ninhydrin 205 was used to test the allyUc esterification, but the desired product 208 was not observed during this process. Indeed, a novel polysubstituted tetracyclic indeno[l,2-fc]indole derivative 207 was obtained. Li and Tu tested then the best conditions and found out that the reaction proceeds nicely in acetic anhydride under microwave conditions in 20-32min with 63-87% yield (Scheme 6.30a). Electron-withdrawing substituents like fluoro, chloro, and bromo in the para-position of the benzene ring as well as electron-donating substituents (Me, OMe) are well tolerated in this reaction. Bulky residues do not cause any problems. 

SCHEME 6.30 Synthesis of multifunctionalized tetracyclic indeno[l,2-fc]indole derivatives 207 and 209. 

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