Regioselectivity of electrophilic aromatic substitution: syntheses of 6-and 7-sulfamoylindolines and-indoles

…, E Chinoporos, MP Filosa, SR Herchen…

Index: Borror, Alan L.; Chinoporos, Efthimios; Filosa, Michael P.; Herchen, Stephen R.; Petersen, Cheryl Pizzo; Stern, Carol A. Journal of Organic Chemistry, 1988 , vol. 53, # 9 p. 2047 - 2052

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Citation Number: 20

Abstract

Figure 1 shows a perspective drawing of the final X-ray model of this indole. The bond lengths and angles agree well with generally accepted values, though the C (6)-C-(7)-C (8) angle is rather small due to the electron-withdrawing effect of the sulfamoyl group at C (6). 6 The indole skeleton of 7b is nearly planar (maximum deviation 0.017 A) but exhibits a slight folding about the ring junction. The N-methylsulfamoyl group is oriented to place the ...