2, 5-Bis-(sulfonyl) pyrazines as unprecedented building blocks and their SN Ar reactions

…, J Guernon, MP Allen, MM Miller, PT Cheng, B Chen

Index: Li, Jie Jack; Meng, Wei; Wu, Shung; Wu, Yong-Jin; Guernon, Jason; Allen, Martin P.; Miller, Michael M.; Cheng, Peter T.; Chen, Bang-Chi Tetrahedron Letters, 2013 , vol. 54, # 15 p. 1938 - 1942

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Abstract

Previously unknown 2, 5-bis-sulfonylpyrazines are prepared and their SNAr reactions are investigated. When 2equiv of thiols are employed, the corresponding bis-thiopyrazines are obtained exclusively. However, phenols or alkoxides gave rise to only the corresponding mono-substituted aryloxy-or alkoxy-sulfonylpyrazines in excellent yields. A carbon nucleophile prepared by treating malonate with NaH also produced the corresponding ...