Cleavage of 2‐(Arylamino)‐4, 6‐dimethoxypyrimidines To Yield Arylguanidines. Issue 17 (23rd April 2014)

• Record Type: Journal Article
• Authors: Shaw, Julian W.; Grayson, David H.; Rozas, Isabel
• Is Part Of: European journal of organic chemistry. Issue 17(2014)
• Page Start: 3565
• Page End: 3569
• Publication Date: 2014-04-23
• Subjects: Synthetic methods -- Cleavage reactions -- Nitrogen heterocycles -- Protecting groups -- Guanidine; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402179
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A novel method for the synthesis of aryl‐substituted guanidines in good overall yields is presented; it consists of the acidic cleavage of 2‐(arylamino)‐4, 6‐dimethoxypyrimidines, which were prepared by coupling aryl bromides with 2‐amino‐4, 6‐dimethoxypyrimidine. This methodology introduces a new means of protection for the guanidine functionality. Abstract : An inexpensive and environmentally friendly method for the synthesis of aryl‐substituted guanidines by the acidic hydrolysis of differently substituted 2‐(arylamino)‐4, 6‐dimethoxypyridines is presented. This methodology introduces a new means of protection for the guanidine functionality; dba = dibenzylideneacetone, Xantphos = 4, 5‐bis(diphenylphosphino)‐9, 9‐dimethylxanthene.