153615-76-0

Upstream product

• 941-69-5 N-phenyl-maleimide 
• 144328-37-0 2-chloro-N-phenyl-2-(phenylthio)succinimide 
• 108-98-5 thiophenol 
• 71724-33-9 1-phenyl-3-(phenylthio)pyrrolidine-2,5-dione 
• 62-53-3 aniline 
• 84649-32-1 α-(phenylthio)maleic anhydride 
• 103056-32-2 3-phenylthio-1-phenyl-1H-pyrrole-2,5-dione 

Downstream Products

• 174676-69-8 8a-(phenylsulfinyl)-4-methyl-7-phenyl-5,5a,8a,8b-tetrahydro-1-oxa-7-aza-as-indacene-6,8-dione 
• 174676-68-7 8a-Benzenesulfinyl-4-(tert-butyl-dimethyl-silanyloxy)-7-phenyl-5,5a,8a,8b-tetrahydro-furo[2,3-e]isoindole-6,8-dione 
• 153615-79-3 2-(2,2'-biindol-3-yl)-N-phenylmaleimide 

Relevant academic research and scientific papers

Site selectivity of the diels-alder reactions of 3-[1-(tert-butyldimethylsilyloxy)vin-1-yl]furan and 3-(propen-2-yl)furan. Synthesis of 4-substituted benzofurans

The Diels-Alder reaction of 3-vinylfurans 5 and 27 with DMAD, N-phenylmaleimide, and dimethyl maleate afforded products derived both from addition to the furan ring diene system (intraannular addition) and to the furan 2,3-double bond 3-vinyl group diene system (extraannular addition). For example, compounds 6 and 7 were obtained from 5 and DMAD. In contrast, dienophiles containing a phenylsulfinyl group, such as 19-21, gave products derived exclusively from the extraannular reaction mode. These products are useful precursors of 4-substituted benzofurans, especially 4-hydroxybenzofurans.

On the Cycloaddition Approach to Indolocarbazoles

2,2'-Biindolyl 9 reacts with electron-deficient dienophiles at 100-110 deg C to give low to moderate yields of Michael addition and formal cycloaddition products, with the former predominant; the products derived from 9 and 2-(phenylsulphinyl)maleimides 14 and 15 undergo in situ elimination of benzenesulphenic acid, leading to 2,2'-biindolyl-substituted maleimides which can be efficiently photocyclised into indolocarbazoles.