Condensation of Carboxylic Acids with Non-Nucleophilic N-Heterocycles and Anilides Using Boc2O

Atsushi Umehara; Hirofumi Ueda; Hidetoshi Tokuyama

doi:10.1021/acs.joc.6b02097

Condensation of Carboxylic Acids with Non-Nucleophilic N-Heterocycles and Anilides Using Boc₂O

Atsushi Umehara, Hirofumi Ueda, Hidetoshi Tokuyama

研究成果: Article › 査読

15 被引用数 (Scopus)

抄録

A novel condensation reaction of carboxylic acids with various non-nucleophilic N-heterocycles and anilides was developed. The reaction proceeds in the presence of di-tert-butyl dicarbonate (Boc₂O), catalytic 4-(dimethylamino)pyridine (DMAP), and 2,6-lutidine and is applicable to the acylation of a wide range of non-nucleophilic nitrogen compounds, including indoles, pyrroles, pyrazole, carbazole, lactams, oxazolidinones, and anilides with high functional group compatibility. The scope of indoles, carboxylic acids, and anilides was also studied.

本文言語	English
ページ（範囲）	11444-11453
ページ数	10
ジャーナル	Journal of Organic Chemistry
巻	81
号	22
DOI	https://doi.org/10.1021/acs.joc.6b02097
出版ステータス	Published - 2016 11月 18

ASJC Scopus subject areas

有機化学

文献へのアクセス

10.1021/acs.joc.6b02097

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引用スタイル

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title = "Condensation of Carboxylic Acids with Non-Nucleophilic N-Heterocycles and Anilides Using Boc2O",

abstract = "A novel condensation reaction of carboxylic acids with various non-nucleophilic N-heterocycles and anilides was developed. The reaction proceeds in the presence of di-tert-butyl dicarbonate (Boc2O), catalytic 4-(dimethylamino)pyridine (DMAP), and 2,6-lutidine and is applicable to the acylation of a wide range of non-nucleophilic nitrogen compounds, including indoles, pyrroles, pyrazole, carbazole, lactams, oxazolidinones, and anilides with high functional group compatibility. The scope of indoles, carboxylic acids, and anilides was also studied.",

author = "Atsushi Umehara and Hirofumi Ueda and Hidetoshi Tokuyama",

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N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Numbers JP16H01127 in Middle Molecular Strategy, JP16H00999 in Precisely Designed Catalysts with Customized Scaffolding, JP15J03530, a Grant-in aid for Scientific Research (A) (26253001), and Young Scientists (B) (26860004). Publisher Copyright: © 2016 American Chemical Society.

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AB - A novel condensation reaction of carboxylic acids with various non-nucleophilic N-heterocycles and anilides was developed. The reaction proceeds in the presence of di-tert-butyl dicarbonate (Boc2O), catalytic 4-(dimethylamino)pyridine (DMAP), and 2,6-lutidine and is applicable to the acylation of a wide range of non-nucleophilic nitrogen compounds, including indoles, pyrroles, pyrazole, carbazole, lactams, oxazolidinones, and anilides with high functional group compatibility. The scope of indoles, carboxylic acids, and anilides was also studied.

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