23456-78-2

Upstream product

• 3400-81-5 2-amino-3-methylcyclohex-2-en-1-one 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 86688-99-5 4-<1-(Phenylsulfonyl)-3-pyrrolyl>butyric acid 
• 344871-28-9 4-(1-Benzenesulfonyl-1H-pyrrol-3-yl)-butyryl chloride 
• 765-87-7 cyclohexane-1,2-dione 
• 108153-93-1 7-oxo-4,5,6,7-tetrahydrobenzofuran 
• 21889-89-4 2,3-epoxy-3-methylcyclohexanone 
• 81454-02-6 4-<1-(Phenylsulfonyl)-3-pyrrolyl>-4-oxobutyric acid 
• 176515-91-6 4-Methyl-N-[2-(5-oxo-7-oxa-bicyclo[4.1.0]hept-1-yl)-ethyl]-benzenesulfonamide 
• 144318-24-1 4-Methyl-N-[2-(3-oxo-cyclohex-1-enyl)-ethyl]-benzenesulfonamide 
• 18159-32-5 Δ¹⁽⁸⁾-hexahydroindole 
• 176516-02-2 1-(Toluene-4-sulfonyl)-1,2,3,4,5,6-hexahydro-indol-7-one 
• 176097-78-2 3a,7,7-trichloro-3,3a,4,5,6,7-hexahydro-2H-indole 
• 86689-00-1 1-(phenylsulfonyl)-1,4,5,6-tetrahydro-7H-indol-7-one 

Downstream Products

• 13618-91-2 4,5,6,7-tetrahydroindole 
• 129053-74-3 1-benzyl-1,4,5,6-tetrahydro-7H-indol-7-one 
• 86689-00-1 1-(phenylsulfonyl)-1,4,5,6-tetrahydro-7H-indol-7-one 
• 1236887-99-2 1-(p-methoxy-benzyl)-1,4,5,6-tetrahydro-7H-indol-7-one 
• 1429641-82-6 C₁₇H₁₉NO₃ 
• 1429641-81-5 C₁₆H₁₇NO₂ 
• 1236887-97-0 1-(p-methyl-benzyl)-1,4,5,6-tetrahydro-7H-indol-7-one 
• 67839-04-7 1-phenyl-1,4,5,6-tetrahydro-7H-indol-7-one 

Relevant academic research and scientific papers

PHOTOCHEMOTHERAPEUTIC HETEROCYCLIC AGENTS HAVING ANTIPROLIFERATIVE AND ANTINEOPLASTIC ACTIVITY

The present invention concerns the synthesis of new analogs of angelicins, pyrrolo [3,2-h]quinoline, for the treatment of pathologies having hyperproliferative character included those having neoplastic nature. The treatment is based on the combined actio

Formation of N-substituted 4- and 7-oxo-4,5,6,7-tetrahydroindoles revisited: A mechanistic interpretation and conversion into 4- and 7-oxoindoles

An efficient method for the preparation of 4-oxo-4,5,6,7-tetrahydroindoles was successfully applied to the synthesis of N-substituted 7-oxo-4,5,6,7- tetrahydroindoles for the first time. Both isomers where converted into their corresponding 4- and 7-oxoindoles in good yields utilizing a novel aromatization protocol. Based on the impurity profile obtained, however, different mechanisms for the formation of the 4- and 7-oxo-4,5,6,7-tetrahydroindole derivatives are discussed. In addition, the reaction sequences appear to be stereospecific allowing for the direct introduction of a chiral center α to the nitrogen and preparation of enantiomerically enriched products.

Synthesis of pyrrolo[3,2-h]quinolinones with good photochemotherapeutic activity and no DNA damage

In the search for new photochemotherapeutic agents, a series of derivatives of the ring system pyrrolo[3,2-h]quinoline - bioisosters of the angular furocoumarin angelicin - were synthesized through a four-step synthetic approach, in reasonable overall yields. Eight of the synthesized derivatives showed a remarkable phototoxicity against a panel of four human tumor cell lines and a great dose UV-A dependence, reaching IC50 values at submicromolar level. The mode of cellular death photoinduced by pyrrolo[3,2-h]quinolines was evaluated through a series of flow cytometric analysis and other tests were performed to clarify their mechanism of action.

Conversion of δ-(sulfonyl)amino-α-epoxy ketones to bicyclic ketopyrroles via intramolecular conjugate-addition to azoene intermediates. Synthesis of the bicyclic ketopyrrole core of the 1-azafulvene roseophilin

Reaction of δ-(sulfonyl)amino-α-epoxy ketones with dimethylhydrazine results in cyclization to pyrrolidine-fused β-hydroxy dimethylhydrazones. Hydrolysis, mesylation, and elimination affords dihydropyrroles which can be converted to sulfonyl-protected ketopyrroles via oxidation with NIS; alternatively, treatment with DBU affords N-H bearing ketopyrroles. Copyright

Novel routes to indoles, indolines, quinolines and tetrahydroquinolines from N-(cyclohexylidene)amines

Cyclohexanones have been converted into a variety of bicyclic azaheterocycles of different oxidation level via a sequence of reactions involving (a) imination, (b) α-alkylation with N,N-disilyl-protected ω-bromoamines, (c) transimination, (d) α-chlorination of the resulting bicyclic imines and (e) dehydrochlorination and/or dehydrogenation. Appropriate choice of the reaction conditions selectively led to reactions to indoles, 7-chloroindoles, 7-chloroindolines, 4,5,6,7-tetrahydroindoles, 8-chloro-1,2,3,4-tetrahydroquinolines, 8-chloroquinolines or quinolines.

Reactions of Some 3-Methylcyclohexenones with Dimethylformamide Dimethyl Acetal

The reactions of 3-methylcyclohexenone, 4-ethoxycarbonyl-3-methylcyclohexenone, isophorone, 2-amino-3-methylcyclohexenone and 2-nitro-3-methylcyclohexenone with dimethylformamide dimethyl acetal have been investigated, and the products characterized.

Regioselective Synthesis of Acylpyrroles

The regioselective synthesis of several pyrrole derivatives is described.AlCl3-catalyzed acylation reactions of 1-(phenylsulfonyl)pyrrole (1) give 3-acyl derivatives, whereas the corresponding BF3*OEt2-catalyzed reactions give 2-acyl derivatives predominantly.Mild alkaline hydrolysis gives the corresponding acyl-1H-pyrroles in excellent yields.AlCl3-catalyzed reactions of 1 with 1,1-dichloromethyl methyl ether and oxalyl chloride give 1-(phenylsulfonyl)-2-formylpyrrole (6) and 1-(phenylsulfonyl)-2-(chlorocarbonyl)pyrrole (7), respectively. 3-Pyrrolylacetic acid (10) was prepared by thallium(III) nitrate promoted rearrangement of 1-(phenylsulfonyl)-3-acetylpyrrole (2a).Trifluoroacetic anhydride catalyzed cyclization of 4-butyric acid (14) gives 1-(phenylsulfonyl)-7-oxo-4,5,6,7-tetrahydroindole (17).Attempts to cyclize 14 at the 4-position have been unsuccessful.