38173-40-9

Upstream product

• 4664-08-8 cinchomeronic anhydride 

Downstream Products

• 99532-65-7 1-(phenylsulfonyl)indol-3-yl 4-carbomethoxy-3-pyridyl ketone 
• 139260-65-4 1-(5-Methoxy-1-phenylsulphonylindol-2-yl)-1-methylfuro<3,4-c>pyridin-3(1H)-one 
• 139260-71-2 4-<1-(5-Methoxy-1-phenylsulphonylindol-2-yl)ethyl>nicotinic Acid 
• 139260-72-3 4-[1-(1-Benzenesulfonyl-5-methoxy-1H-indol-2-yl)-ethyl]-N-(2-dimethylamino-ethyl)-nicotinamide 
• 139260-59-6 4-[1-(1-Benzenesulfonyl-5-methoxy-1H-indol-2-yl)-ethyl]-N-(3-diethylamino-propyl)-nicotinamide 
• 139260-70-1 4-<1-Hydroxy-1-(5-methoxy-1-phenylsulphonylindol-2-yl)-ethyl>-N,N-diisopropylnicotinamide 

Relevant academic research and scientific papers

Synthesis of 11-Amino-substituted-9-methoxy-5-methyl-6H-pyridocarbazoles

A route to 11-amino-substituted-6H-pyridocarbazoles has been studied.Thus, condensation of 2-(4-lithiopyridine-3-yl)-4,4-dimethyloxazoline with 2-acetyl-5-methoxy-1-phenylsulphonylindole led to a low yield of the expected alcohol, which upon hydrolysis gave a complex mixture.A better starting building block was 4-acetyl-N,N-diisopropylnicotinamide obtained either from N,N-diisopropyl-4-lithionicotinamide (low yield) or from pyridine-3,4-dicarboxylic anhydride, using a 4-step sequence.This compound was treated with 2-lithio-5-methoxy-1-phenylsulphonylindole, affording N,N-diisopropyl-4-nicotinamide.Hydrolysis and then reduction led to 4-nicotinic acid whose amides were cyclized by phosphorus trichlorideoxide.Finally, the title compounds were obtained by Raney-nickel reduction-elimination of the 6-phenylsulphonyl protecting group.

A Convenient Synthesis of 3-Acylindoles via Friedel-Crafts Acylation of 1-(Phenylsulfonyl)indole. A New Route to Pyridocarbazole-5,11-quinones and Ellipticine

A Friedel-Crafts acylation of 1-(phenylsulfonyl)indoles (1) with carboxylic acid anhydrides and acid chlorides in the presence of aluminum chloride gives 3-acyl-1-(phenylsulfonyl)indoles (2) in 81-99percent yields.Base hydrolysis converts 2 to 3-acylindoles (3) in 79-96percent yields.The reaction of 1-(phenylsulfonyl)indole (1a) with oxalyl chloride gives acid chloride 2h, which is converted to 3-cyanoindole (7) in three steps (75percent yield).Although a similar Friedel-Crafts alkylation of 1 was unsuccessful, in some cases the 3-acyl-1-(phenylsulfonyl)indoles 2a,e,f could be reduced to 3-alkyl-1-(phenylsulfonyl)indoles 8a,b,c in nearly quantitative yield with sodium borohydride in trifluoroacetic acid.The acid chloride derived from keto acid 9 did not cyclize to the desired pyridocarbazole-5,11-quinone 24 but rather to chloro keto lactam 10.However, acylation of 1a with acid chloride 22 followed by strong-base-mediated cyclization gives 24.Since quinone 24 has been previously converted to the alkaloid ellipticine 26, this route to 24 represents a new synthesis of ellipticine.Related synthetic schemes give rise to quinones 16 and 20.