One‐Pot SNAr/Direct Pd‐Catalyzed CH Arylation Functionalization of Pyrazolo[1, 5‐a]pyrimidine at the C3 and C7 Positions. Issue 29 (10th July 2018)

• Record Type: Journal Article
• Authors: Loubidi, Mohammed; Manga, Catherine; Tber, Zahira; Bassoude, Ibtissam; Essassi, El Mokhtar; Berteina‐Raboin, Sabine
• Is Part Of: European journal of organic chemistry. Issue 29(2018)
• Page Start: 3936
• Page End: 3942
• Publication Date: 2018-07-10
• Subjects: Nitrogen heterocycles -- Arylation -- Homogeneous catalysis -- Amination; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201800580
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : An efficient and original synthesis of various 3, 7‐substituted pyrazolo[1, 5‐ a ]pyrimidines is reported. First, a two‐step process by an SN Ar amination followed by a Pd‐catalyzed direct CH‐arylation was developed, then a parallel single‐pot SN Ar amination/CH arylation sequence was performed starting from 7‐chloro‐5‐methyl‐2‐phenylpyrazolo[1, 5‐ a ]pyrimidine to obtain highly functionalized products with good yields. Abstract : We report in this paper a novel and efficient protocol for the synthesis of a 3, 7‐disubstituted pyrazolo[1, 5‐ a ]pyrimidine library by an SN Ar amination followed by palladium‐catalyzed direct arylation.