176327-46-1

Basic information

• Product Name: N-(benzenesulfonyl)-3-iodoindole-2-carboxaldehyde
• Synonyms: N-(benzenesulfonyl)-3-iodoindole-2-carboxaldehyde
• CAS NO: 176327-46-1
• Molecular Weight: 411.22
• Mol File: 176327-46-1.mol

Chemical Properties

• CAS DataBase Reference: N-(benzenesulfonyl)-3-iodoindole-2-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: N-(benzenesulfonyl)-3-iodoindole-2-carboxaldehyde(176327-46-1)
• EPA Substance Registry System: N-(benzenesulfonyl)-3-iodoindole-2-carboxaldehyde(176327-46-1)

Safety Data

• Hazardous Substances Data: 176327-46-1(Hazardous Substances Data)

Upstream product

• 19005-93-7 1H-indol-2-ylcarboxaldehyde 
• 80360-14-1 3-iodo-1-phenylsulfonyl-1H-indole 
• 109-94-4 formic acid ethyl ester 
• 98-09-9 benzenesulfonyl chloride 
• 176327-44-9 3-iodo-1H-indole-2-carboxaldehyde 

Downstream Products

• 258497-56-2 3-(phenylethynyl)-1-(phenylsulfonyl)indole-2-carbaldehyde 
• 752212-08-1 3-allyl-1-benzenesulfonyl-1H-indole-2-carbaldehyde 
• 91944-01-3 3-phenyl-9H-pyrido[3,4-b]indole 
• 1313739-68-2 N-[(3-iodo-1-phenylsulfonyl-1H-indol-2-yl)methyl]-N-methylamine 
• 1313739-69-3 4-{N-[(3-iodo-1-phenylsulfonyl-1H-indol-2-yl)methyl]-N-methylamino}-2-butanone 
• 1313739-70-6 1-{N-[(3-iodo-1-phenylsulfonyl-1H-indol-2-yl)methyl]-N-methylamino}-2-propanone 
• 1313739-83-1 1-acetyl-2-methyl-4-phenylsulfonyl-2,4-dihydropyrrolo[3,4-b]indole 
• 1562039-07-9 2-(1-hydroxyprop-2-en-1-yl)-3-iodo-N-(phenylsulfonyl)indole 
• 1562039-18-2 2-[1-(tert-butyldimethylsilyloxy)prop-2-en-1-yl]-3-iodo-N-(phenylsulfonyl)indole 
• 188037-50-5 1-Benzenesulfonyl-2-(1-methoxymethoxy-prop-2-ynyl)-3-vinyl-1H-indole 
• 188037-59-4 1-(1-Benzenesulfonyl-3-vinyl-1H-indol-2-yl)-prop-2-yn-1-ol 
• 403642-58-0 1-benzenesulfonyl-3-(3-hydroxy-3-methyl-but-1-ynyl)-1H-indole-2-carbaldehyde 
• 188037-54-9 1-Benzenesulfonyl-3-vinyl-1H-indole-2-carbaldehyde 
• 176327-47-2 N-(benzenesulfonyl)-3-(2-ethoxyethenyl)indole-2-carboxaldehyde 

Relevant articles and documents

Total synthesis of carazostatin and hyellazole by allene-mediated electrocyclic reaction

The free radical scavenger carazostatin and the marine alkaloid hyellazole have been synthesized by a new type of allene-mediated electrocyclic reaction involving the indole 2,3-bond as a key step.

Synthesis of β-carbolines from 2-Acyl-1-benzenesulfonyl-3-iodo-1H-indoles

2-Acyl-1-benzenesulfonyl-3-iodo-1H-indoles and 1-benzenesulfonyl-3-iodo-1H-indole-2-carbaldehyde give in satisfactory yields 1,3- and 3-substituted-β-carbolines, respectively, by combined palladium-catalyzed coupling with alk-1-ynes followed by 6-endo-dig

Total Syntheses of Carazostatin, Hyellazule, and Carbazoquinocins B-F

Total syntheses of carazostatin (1), hyellazole (2a), and carbazoquinocins B-F (3b-f) have been completed. The cross-coupling reaction between 3-iodoindole 8 and vinylstannane 11b gave the 3-alkenylindole 7. Treatment of 7 with ethynylmagnesium bromide, followed by etherification of the resulting alcohol 12 with MOMCl, yielded the 3-alkenyl-2-propargylindole 6. The compound 6 was treated with t-BuOK in t-BuOH at 90°C to obtain the desired carbazoles 4 together with the N-deprotected carbazole 13 through an allene-mediated electrocyclic reaction. The carbazole 13a, derived from 4a or 4c, was converted into the triflate 24 in two steps. The triflate 24 was subjected to the Suzuki cross-coupling reaction with either 9-heptyl-9-BBN or phenylboronic acid in the presence of a palladium catalyst to produce the 1-heptylcarbazole 25a and the 1-phenylcarbazole 25b. Cleavage of the ether bond of 25a yielded carazostatin (1). Cleavage of the ether bond of 25b followed by O-methylation gave hyellazole (2a). Oxidation of carazostatin (1) with benzene seleninic anhydride afforded carbazoquinocin C (3c). In a similar way, carbazoquinocins B and D-F (3b,d-f) were synthesized, respectively.