Synthesis of Passerini adducts from aldehydes and isocyanides under the auxiliary of water

Literature Information

Publication Date 2015-07-23
DOI 10.1039/C5QO00202H
Impact Factor 5.281
Authors

Ming Li, Bin Qiu, Xiang-Jing Kong, Li-Rong Wen


View Original

Abstract

An efficient protocol for the synthesis of the Passerini adducts α-acyloxycarboxamides from aldehydes, isocyanides and water in a molecular ratio of 3 : 1 : 3 was described. The possible mechanism for the reaction was discussed by employing cross condensation and H218O isotope labeling experiments. This method offers a straightforward access to α-acyloxycarboxamides bearing two identical functional groups in high yields under mild conditions.

Related Literature

An umpolung strategy for chemoselective metal-free [4 + 2] annulation of azlactones: access to tetrahydro-β-carbolin 1,3-diketone frameworks

Meng Wang, Ze-Hong Zheng, Mu-Qiu Chen, Gu Zhan, Jie Wang, Qian-Qian Yang, Wei Huang

2023-12-12 Research Article

DOI: 10.1039/D3QO01184D

Photoredox Suzuki coupling using alkyl boronic acids and esters

Kanak Kanti Das, Somenath Mahato, Debraj Ghorai, Sutapa Dey, Santanu Panda

2023-12-14 Research Article

DOI: 10.1039/D3QO01838E

Divergent synthesis of 3,4-dihydro-2H-benzo[h]chromen-2-one and fluorenone derivatives from ortho-alkynylarylketones

Jantra Jantrapirom, Nitwaree Palavong

2023-10-25 Paper

DOI: 10.1039/D3OB01492D

A de novo synthesis of the bisindole alkaloid geissolosimine: collective synthesis of geissoschizoline, akuammicine, (16S)-deshydroxymethylstemmadenine and Aspidospermatan alkaloids

Jiahang Yan, Yanxia Zhen, Pengyan Wang, Yimeng Han, Huanhuan Zou, Junhan Chen, Weigang He

2023-12-04 Research Article

DOI: 10.1039/D3QO01898A

Ni-catalyzed regioselective C–C bond formation of 1,1-disubstituted allenes with aldehydes

Seoyeon Kim, Jinyoung Kim, Shrikant D. Tambe, Eun Jin Cho

2023-12-11 Research Article

DOI: 10.1039/D3QO01800H

Halogen bonding and mechanochemistry combined: synthesis, characterization, and application of N-iodosaccharin pyridine complexes

Khai-Nghi Truong, Jas S. Ward, Rakesh Puttreddy, Anssi Rajala, Elias Lassila, Carsten Bolm, Kari Rissanen

2023-12-05 Research Article

DOI: 10.1039/D3QO01512B

Olefination of aldehydes with alpha-halo redox-active esters

Zhengqiang Liu, Wenbo H. Liu

2023-12-14 Research Article

DOI: 10.1039/D3QO01805A

Hydantoin hexameric rosettes: harnessing H-bonds for supergelation and liquid crystals

Lucía González, Iván Marín, Rosa M. Tejedor, Joaquín Barberá, Pilar Romero, Alberto Concellón, Santiago Uriel, José L. Serrano

2023-12-04 Research Article

DOI: 10.1039/D3QO01832F

Carbon atom insertion into N-heterocyclic carbenes to yield 3,4-dihydroquinoxalin-2(1H)-ones

Justin S. Lamb, Futa Koyama, Noriyuki Suzuki, Yumiko Suzuki

2023-11-10 Research Article

DOI: 10.1039/D3QO01579C

You might also like

Compound Q&A

How should 2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) be stored?

2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) should be stored in ...

615-45-22-Methylbenzene-1,4-...
Compound Q&A

Is (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide (CAS: 132747-20-7) safe?

(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is generally considered sa...

132747-20-7(1S,4S)-2,5-Diazabic...
Compound Q&A

What industries use (6-Chloropyridazin-3-YL)methanamine (CAS: 871826-15-2)?

(6-Chloropyridazin-3-YL)methanamine finds applications in the pharmaceutical ind...

871826-15-2(6-Chloropyridazin-3...
Compound Q&A

What are the main uses of 2-Fluoro-3-methylphenol (CAS: 77772-72-6)?

2-Fluoro-3-methylphenol is primarily used in the synthesis of pharmaceuticals, p...

77772-72-62-Fluoro-3-methylphe...
Compound Q&A

What precautions should be taken when handling 3-Methoxy-4-nitrobenzonitrile (CAS: 177476-75-4)?

When handling 3-Methoxy-4-nitrobenzonitrile, it is important to wear appropriate...

177476-75-43-Methoxy-4-nitroben...
Compound Q&A

What precautions should be taken when handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4)?

When handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4), it is ...

211949-57-4[1,3]Oxazolo[4,5-b]p...
Compound Q&A

What regulatory guidelines apply to 4-Ethynylbenzamide (CAS: 90347-86-7)?

4-Ethynylbenzamide (CAS: 90347-86-7) falls under various regulatory guidelines i...

90347-86-74-Ethynylbenzamide
Compound Q&A

What are the main uses of 3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone (CAS: 186822-57-1)?

3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone is primarily used as an intermediat...

186822-57-13-(2-Ethylphenyl)-2-...
Compound Q&A

What is (2-Fluoro-6-methoxyphenyl)acetic acid (CAS: 500912-19-6)?

(2-Fluoro-6-methoxyphenyl)acetic acid, also known as 4-fluoro-3-methoxybenzoic a...

500912-19-6(2-Fluoro-6-methoxyp...
Compound Q&A

What is the market or research trend for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9)?

Market trends for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9) indicat...

102196-18-92-[4-(Hydroxymethyl)...

Source Journal

Organic Chemistry Frontiers

Organic Chemistry Frontiers
CiteScore: 7.8
Self-citation Rate: 8.7%
Articles per Year: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.