Condensation of Carboxylic Acids with Non-Nucleophilic N-Heterocycles and Anilides Using Boc2OClick to copy article linkArticle link copied!
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.
Cited By
This article is cited by 16 publications.
- Noriyoshi Arai, Takeshi Ohkuma. Photosensitized Intramolecular [2+2] Cycloaddition of 1H-Pyrrolo[2,3-b]pyridines Enabled by the Assistance of Lewis Acids. The Journal of Organic Chemistry 2020, 85
(23)
, 15717-15725. https://doi.org/10.1021/acs.joc.0c02231
- Zhijie Zhang, Dong Yi, Min Zhang, Jun Wei, Ji Lu, Lin Yang, Jun Wang, Na Hao, Xianchao Pan, Shiqi Zhang, Siping Wei, Qiang Fu. Photocatalytic Intramolecular [2 + 2] Cycloaddition of Indole Derivatives via Energy Transfer: A Method for Late-Stage Skeletal Transformation. ACS Catalysis 2020, 10
(17)
, 10149-10156. https://doi.org/10.1021/acscatal.0c01841
- Noriyoshi Arai, Takeshi Ohkuma. Stereoselective Construction of Methylenecyclobutane-Fused Indolines through Photosensitized [2+2] Cycloaddition of Allene-Tethered Indole Derivatives. Organic Letters 2019, 21
(5)
, 1506-1510. https://doi.org/10.1021/acs.orglett.9b00309
- D. M.
M. Mevan Dissanayake, Aaron K. Vannucci. Selective N1-Acylation of Indazoles with Acid Anhydrides Using an Electrochemical Approach. Organic Letters 2019, 21
(2)
, 457-460. https://doi.org/10.1021/acs.orglett.8b03683
- Fei-Fan Meng, Jia-Hao Xie, Yun-He Xu, Teck-Peng Loh. Catalytically Asymmetric Synthesis of 1,3-Bis(silyl)propenes via Copper-Catalyzed Double Proto-Silylations of Polar Enynes. ACS Catalysis 2018, 8
(6)
, 5306-5312. https://doi.org/10.1021/acscatal.8b00999
- Atsushi Umehara, Soma Shimizu, Makoto Sasaki. DMAPO/Boc
2
O‐Mediated One‐Pot Direct
N
1‐Acylation of Indazole with Carboxylic Acids: A Practical Synthesis of
N
1‐Functionalized Alkyl Indazoles. European Journal of Organic Chemistry 2024, 27
(18)
https://doi.org/10.1002/ejoc.202400123
- Atsushi Umehara, Soma Shimizu, Makoto Sasaki. Synthesis of Bulky
N
‐Acyl Heterocycles by DMAPO/Boc
2
O‐Mediated One‐Pot Direct
N
‐Acylation of Less Nucleophilic
N
‐Heterocycles with α‐Fully Substituted Carboxylic Acids. Advanced Synthesis & Catalysis 2023, 365
(14)
, 2367-2376. https://doi.org/10.1002/adsc.202300487
- Atsushi Umehara, Soma Shimizu, Makoto Sasaki. DMAPO/Boc
2
O‐Mediated One‐Pot Direct
N
‐Acylation of Less Nucleophilic
N
‐Heterocycles with Carboxylic Acids. ChemCatChem 2023, 15
(5)
https://doi.org/10.1002/cctc.202201596
- Dandan Shang, Rui Hu, Qing Bao, Jichao Chen, Lei Yu, Philip Wai Hong Chan, Weidong Rao. PtI
4
-catalyzed oxidative and hydrogenative dearomative [3 + 2] cycloaddition of 1
H
-indole
N
-tethered
o
-alkynylbenzaldehydes. Organic Chemistry Frontiers 2022, 10
(1)
, 140-149. https://doi.org/10.1039/D2QO01520J
- Yutong Lin, Lara R. Malins. Synthesis of Peptide N-Acylpyrroles via Anodically Generated N,O-Acetals. Synthesis 2022, 54
(16)
, 3558-3567. https://doi.org/10.1055/s-0041-1737411
- Jisoo Woo, Alec H. Christian, Samantha A. Burgess, Yuan Jiang, Umar Faruk Mansoor, Mark D. Levin. Scaffold hopping by net photochemical carbon deletion of azaarenes. Science 2022, 376
(6592)
, 527-532. https://doi.org/10.1126/science.abo4282
- Keyvan Pedrood, Saeed Bahadorikhalili, Vahid Lotfi, Bagher Larijani, Mohammad Mahdavi. Catalytic and non-catalytic amidation of carboxylic acid substrates. Molecular Diversity 2022, 26
(2)
, 1311-1344. https://doi.org/10.1007/s11030-021-10252-0
- Mahesh H. Shinde, Chepuri V. Ramana. Facile synthesis of the spiro-pyridoindolone scaffold
via
a gold-catalysed intramolecular alkynol cyclisation/hydroindolylation. Organic & Biomolecular Chemistry 2022, 20
(10)
, 2086-2095. https://doi.org/10.1039/D1OB02483C
- Tianri Du, Xiangmu Wei, Honghong Xu, Xin Zhang, Ruiru Fang, Zheng Yuan, Zhi Liang, Yahui Li. Chemoselective
N
-acylation of indoles using thioesters as acyl source. Beilstein Journal of Organic Chemistry 2022, 18 , 89-94. https://doi.org/10.3762/bjoc.18.9
- Thoota Sandeep Kumar, Alice R. Robert, Himavathi Ganja, Pamerla Muralidhar, Kerru Nagaraju, Suresh Maddila. Purification free, chemoselective N-acylation of non-nucleophilic nitrogen heterocycles using oxyma and benzotriazole activations. Chemical Data Collections 2021, 32 , 100654. https://doi.org/10.1016/j.cdc.2021.100654
- Linda Ta, Henrik Sundén. Oxidative organocatalytic chemoselective
N
-acylation of heterocycles with aromatic and conjugated aldehydes. Chemical Communications 2018, 54
(5)
, 531-534. https://doi.org/10.1039/C7CC08672E
Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.
Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.