A dipolar cycloaddition approach to pyrrolo [1, 2-a] indoles using N-[(trimethylsilyl) methyl]-substituted indoles

…, JR Gasdaska, MK Venkatramanan…

Index: Padwa, Albert; Fryxell, Glen E.; Gasdaska, John R.; Venkatramanan, M. K.; Wong, George S. K. Journal of Organic Chemistry, 1989 , vol. 54, # 3 p. 644 - 653

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Citation Number: 56

Abstract

The 1, 3-dipolar cycloaddition of a number of N-[(trimethylsily1) methyll-substituted indoles with several dipolarophiles has been investigated. The reaction requires the use of an equivalent amount of silver fluoride and provides a direct and efficient synthesis of the pyrrolo [l, 2-a] indole ring system. The structures of the cycloadducts were established by high-field NMR spectroscopy as well as by several X-ray crystal structures. The ...