Benz indol-2

Intramolecular acylation of l-benzyl-2-(2-carboxybenzoyl)pyrrole under Friedel-Crafts conditions yields l//-benz[/]indole-4,9-dione (79KGS1564). When the 1-position is unsubstituted, cyclization occurs to that position (B-77MI30502). 

This methodology has since been applied to constructing [6]-an-nelated carbazoles, and benz[/]indole, and the tetracyclic skeleton of the benzophenanthridine alkaloids. Arynes used in this type of reaction include 3,4-didehydropyridine in the synthesis of ellipticine 8 and isoellipticine 9," 3,4-(methylenedioxy)benzyne, and 2,3-naphthalyne. ... 

Lin and colleagues expanded the Nenitzescu indole synthesis to include a wide variety of 1,3-diazaheterocycle-fused [l,2-fl]indoles (Scheme 13, equation 1 and 55-57) [51], Parr and Reiss employed the Nenitzescu indole synthesis to prepare several benz[ ]indoles and 1,2-annulated indoles (equations 2, 3) [52]. 

Suginome and coworkers discovered the novel [3+2] regioselective photoaddilion of 2-amino-1,4-naphthoquinones with electron-rich alkenes to afford lH-benz[/] indole-4,9-diones (Schane 16, equation 1) [112]. Likewise, amino-1,4-benzoquinones with alkenes gave lH-indole-4,7-diones (equation 2). If the initial photoproducts could not indolize by loss of alcohoL then the corresponding dihydro compounds were isolated. Parker and Mindt found that qui-none monoimides were smoothly photocyclized to the respective 5-hydroxyindoles (equation 3) [113]. 

The thermal chemistry of a number of related aryl-substituted 2/f-azirines were also studied. The 2-naphthyl-substituted azirines 299 were found to rearrange to benz[g]indole 300. The selectivity encountered here was attributed to the higher energy content of the intermediate leading to the alternative benz[/]indole system 302. Heteroaromatic systems were also found to undergo thermal rearrangement via highly selective reaction paths ... 

SCHEME 2.38 N-Vinylation of benz[ ]indole with acetylene. 

The condensed indole, benz[ ]indole, under the same conditions, is coupled with benzoylbromoacetylene to furnish a mixture of 3- and 2-benzoylethynylindoles in a 45% overall yield (Scheme 2.59, Table 2.6). In this case, 2-(2-benzoyl-l-bromovinyll) benz[ ]indole, stabilized by strong intramolecular hydrogen bonding between the NH and C=0 groups (5 NH 14.59 ppm), is also detected ( H NMR) [523]. 

Miao L, Haque 1, Manzoni MR, Tham WS, Chemler Sr., Diastereo- and enantioselective copper-catalyzed intramolecular carboamination of alkenes for the synthesis of hexahydro-l/f-benz[/]indoles. Org. Lett. 2010 12(21) 4739-4741. 

Many names in common use for heteropolycycles provide little or no information about structure. Most such names were introduced long before any serious attempts were made to systematize nomenclature, and although more systematic equivalents can now be coined in many cases (for example, indole can be named benz[f)]azole or 1-azacyclopentabenzene), it is likely that the use of a substantial residue of trivial names will continue. However, one would not expect many new trivial names to be introduced in the future, except in the natural product area (see Section 1.02.4). 

A synthetic approach to the same tetracyclic y-carboline nucleus (235) is the consecutive Fischer indole and Bischler-Napieralski ring closure of o-acetamidoacetophenone methylphenyUiydrazone (234). The Bischler-Napieralski reaction has also been used in the synthesis of 3,4-benz-j8-carbolines (236) and 3,4-benz-3-carbolines, e.g. 237... 

Thermolysis of the vinyl azide 11 in toluene furnishes a mixture of ethyl 2-phenyl-l//-3-benz-azepine-4-carboxylate(12), ethyl 4-(2-phenylvinyl)indole-2-carboxylate(13) and ethyl 1-benzyl-isoquinoline-3-carboxylate (14).82... 

Thermolysis of the vinyl azide 26 in xylene yields ethyl 8-(mcthoxymcthyl)-l,8-dihydro-benz[2,3]azepino[4,5- >]indole-2-carboxylate (27) by attack of the vinyl nitrene at the 2-phenyl group.83... 

Dimethylamino-benzoyl)-indol — 3-(4-Dimethylamino-benz l)-indoP 83,4% d.Th. ... 

CN 5-(4,5-dihydro-2-phenyl-3//-benz[e]indol-3-yl)-2-hydroxybenzoic acid... 

Spray solution For indole derivatives Dissolve 50 mg 4-(dimethylamino)-benz-... 

For indole derivatives Dissolve 50 mg 4-(dimethylamino)-benz-aldehyde in 1 ml cone, sulfuric acid and make up to 100 ml with 95% ethanol [7]. 

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