K2CO3-accelerated amidation of carboxylic acids using α-oxo ketene-N,S-acetals as amine surrogates

被引：3

作者：

Yu, Haifeng ^{[1
]}

Zhang, Xue ^{[1
]}

Li, Liangliang ^{[1
]}

Luo, Hui ^{[1
]}

Che, Guangbo ^{[1
]}

机构：

[1] Baicheng Normal Univ, Coll Chem, Baicheng 137000, Jilin, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 03期

关键词：

C-H AMIDATION; KETENE DITHIOACETALS; COUPLING REAGENTS; AMIDE FORMATION; ANNULATION; N; S-ACETALS; ALDEHYDES; ACCESS;

D O I：

10.1039/d2qo01716d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and efficient K2CO3-accelerated amidation of carboxylic acids with alpha-oxo ketene-N,S-acetals as amine surrogates is developed. The amidation of carboxylic acids is achieved in the presence of 10 mol% of K2CO3 using readily available (E)-4-(alkylamino)-4-(ethylthio)but-3-en-2-ones as amine surrogates. The method represents the first example of the synthetic utility of C-N bond cleavage of alpha-oxo ketene-N,S-acetals. A plausible mechanism is proposed on the basis of the detailed studies, in which the base plays the key role during the transformation.

引用

页码：686 / 698

页数：13

共 24 条

[1] NaOH promoted hydrolysis of α-oxo ketene-N, S-acetals: Effective synthesis of β-keto amides
Li, Liangliang
Jiang, Chunxu
Peng, Tingting
Zhang, Nuonan
Ji, Jing
Yu, Haifeng
Zhao, Xiaobo
SYNTHETIC COMMUNICATIONS, 2024, 54 (04) : 312 - 320
[2] Studies on the alkylation of β-oxo thioamides with α-bromoketones:: Selective cyclization of the intermediate α-oxo ketene-N,S-acetals to thiophene derivatives
Suma, S
Ushakumari, NK
Asokan, CV
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1997, 131 : 161 - 171
[3] Aryl radical cyclizations of N-(2-halobenzoyl)-cyclic ketene-N,S-acetals
Zhou, AH
Pittman, CU
TETRAHEDRON LETTERS, 2005, 46 (22) : 3801 - 3805
[4] A convenient synthesis of pyrazolylpyrazoles using α-oxo ketene S,S- and N,S-acetals
Chen, HS
Li, ZM
Wang, ZW
CHINESE CHEMICAL LETTERS, 1999, 10 (08) : 643 - 646
[5] Reactions of 2-methylthiazolines and N-methyl cyclic ketene-N,S-acetals with acid chlorides
Zhou, AH
Pittman, CU
TETRAHEDRON LETTERS, 2004, 45 (48) : 8899 - 8903
[6] A Convenient Synthesis of Pyrazolylpyrazoles Using α-Oxo Ketene S,S- and N,S-Acetals
Han Song CHEN
Zheng Ming LI
Zhong Wen WANG (State Key Laboratory of Elemento-Organic Chemistry
Chinese Chemical Letters, 1999, (08) : 643 - 646
[7] Preparation of thieno[2,3-b]pyrroles starting from ketene-N,S-acetals
Sommen, G
Comel, A
Kirsch, G
TETRAHEDRON, 2003, 59 (09) : 1557 - 1564
[8] CYCLOADDITION REACTIONS OF CYCLIC KETENE-N,S-ACETALS WITH 1,2,4,5-TETRAZINES
MARCELIS, ATM
VANDERPLAS, HC
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (03) : 545 - 548
[9] POLARIZED KETENE S,S-ACETALS AND S,N-ACETALS .64. SYNTHESIS OF METHYL 5-ARYL-3-OXO-4-PENTENOATES AND NOVEL SUBSTITUTED CYCLOPENTENONES
ASOKAN, CV
BHATTACHARJI, S
ILA, H
JUNJAPPA, H
SYNTHESIS-STUTTGART, 1988, (04): : 281 - 283
[10] Vilsmeier cyclization of α-acetyl-α-aroyl ketene-N,S-acetals: direct and efficient synthesis of halogenated pyridin-2(1H)-ones
Yu, Haifeng
Zhang, Yongmei
Li, Tiechun
Liao, Peiqiu
Diao, Quanping
Xin, Guang
Meng, Qingling
Hou, Dongyan
RSC ADVANCES, 2015, 5 (15): : 11293 - 11296

← 1 2 3 →