251089-11-9

Upstream product

• 616-38-6 carbonic acid dimethyl ester 
• 251089-10-8 3-(o-nitrophenyl)-1H-quinoline-2-one 
• 552-89-6 2-nitro-benzaldehyde 
• 529-23-7 o-aminobenzaldehyde 
• 941-91-3 3-bromo-1-methylquinolin-2(1H)-one 
• 190788-59-1 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene 
• 91-22-5 quinoline 
• 79476-07-6 3-Iodoquinoline 
• 5570-19-4 2-nitrophenylboronic acid 
• 138037-41-9 3-iodo-1-methylquinolin-2(1H)-one 
• 3947-76-0 N-methylquinolinium iodide 
• 251089-13-1 (E)-2-nitro-2'-(triphenylphosphoranylidene)aminostilbene 
• 365529-80-2 C₁₅H₁₀N₂O₃ 
• 251089-08-4 (Z)-2-amino-2'-nitrostilbene 

Downstream Products

• 114414-78-7 neocryptolepine 
• 251089-12-0 1-methyl-3-(o-azidophenyl)-1H-quinoline-2-one 
• 197524-37-1 1-methyl-3-(o-aminophenyl)-1H-quinoline-2-one 

Relevant academic research and scientific papers

Iodination/Amidation of the N-Alkyl (Iso)quinolinium Salts

The NaIO4-mediated sequential iodination/amidation reaction of N-alkyl quinolinium iodide salts has been first developed. This cascade process provides an efficient way to rapidly synthesize 3-iodo-N-alkyl quinolinones with high regioselectivity and good functional group tolerance. This protocol was also amenable to the isoquinolinium salts, thus providing a complementary method for preparing the 4-iodo-N-alkyl isoquinolinones.

Regioselective Synthesis of Chirally Enriched Tetrahydrocarbazolones and Tetrahydrocarbazoles

A new one-step, reagent-directed regioselective synthesis of chirally enriched tetrahydrocarbazolones and tetrahydrocarbazoles from a common type of substrate has been developed. The salient features of this method include inherited stereodiversity, a bro

Efficient total synthesis of neocryptolepine and synthetic access to 6-methylquinindoline from a common intermediate

A convenient approach toward the indoloquinolines neocryptolepine and 6-methylquinindoline from a common intermediate, is reported. Both sequences, designed for maximum use of accessible reagents and robust conditions, are straightforward and efficient. They involved the amidation of 2-aminobenzaldehyde (prepared by iron-mediated reduction of 2-nitrobenzaldehyde) with 2-nitrophenylacetic acid, followed by a K2CO3-assisted cyclization to form a 3-(2-nitrophenyl)quinolin-2-one as the common precursor. Me2CO3-mediated N-methylation of the lactam, reduction of the nitro moiety and final cyclization resulted in 55% overall yield of neocryptolepine, whereas cyclocondensation and N-methylation afforded 79% overall yield of 6-methyl quinindoline. Thus, the sequences toward the targets entailed two POCl3-promoted C-N bond forming reactions, two Fe-mediated nitro group reductions and two base-promoted transformations.

A novel approach to the indoloquinoline alkaloids cryptotackieine and cryptosanguinolentine by application of cyclization of o-vinylsubstituted arylheterocumulenes

1-Methyl-3-(o-azidophenyl)quinoline-2-one prepared by cyclization of the corresponding o-vinylsubstituted isocyanate under microwave irradiation is directly converted into cryptotackieine 1 by an intramolecular aza-Wittig reaction with trimethylphosphine; alternatively heating followed by reduction of the resulting indoloquinoline derivative provided cryptosanguinolentine 2.

A divergent approach to cryptotackieine and cryptosanguinolentine alkaloids

A seven-step synthesis of the 1-methyl-3-(o-azidophenyl)quinolin-2-one, a common intermediate for the synthesis of the cryptotackieine and cryptosanguinolentine alkaloids, is described. This intermediate is directly converted into cryptotackieine 1 by an intramolecular aza-Wittig reaction with trimethylphosphine; alternatively heating followed by reduction of the resulting indoloquinoline derivative provided cryptosanguinolentine 2.