New synthesis of (Z,E)-2,7-bis(4-cyanobenzylidene)cycloheptan-1-one under stereospecific constraints induced by host–guest interactions

Literature Information

Publication Date 2005-07-12
DOI 10.1039/B504989J
Impact Factor 6.222
Authors

Arnaud Grandeury, Samuel Petit, Servane Coste, Gérard Coquerel, Cécile Perrio, Géraldine Gouhier


View Original

Abstract

A selective, efficient, and fast access to (Z,E)-2,7-bis(4-cyanobenzylidene)cycloheptan-1-one (BCBCH), precursor of the synthetic antagonist of tissue-plasminogen activator (t-PA), is reported using a solid/solid aldolisation–crotonisation reaction on a supramolecular complex under microwave irradiation. The underlying mechanism is investigated from the crystal structure of the intermediate host–guest complex formed between permethylated γ-cyclodextrin and (Z)-2-(4-cyanobenzylidene)cycloheptan-1-one.

Related Literature

Front cover

2024-01-16 Cover

DOI: 10.1039/D4QO90005G

Atroposelective synthesis of N–N axially chiral pyrrolyl(aza)-quinolinone by de novo ring formation

Qiwen Huang, Yanze Li, Cun Yang, Wendan Wu, Jingjie Hai, Xinyao Li

2023-12-04 Research Article

DOI: 10.1039/D3QO01877F

Visible light photoredox-catalyzed deoxydisulfuration of alcohols

Chaoyang Liu, Xiaoman Lin, Delie An

2023-11-22 Research Article

DOI: 10.1039/D3QO01742G

Electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens involving C–S/Se bond formation

Jianchao Liu, Jie-Ping Wan, Yunyun Liu

2023-11-23 Review Article

DOI: 10.1039/D3QO01844J

A novel three-component coupling reaction of aryne, CN derivatives, and acrylonitrile

Yangang Wu, Wenbo Cai, Lulu Yu, Junbiao Chang, Chuanjun Song

2023-11-13 Research Article

DOI: 10.1039/D3QO01454A

A catalyst-free cross-coupling of isocyanates and triarylboranes for secondary amide synthesis

You-Wei Wu, Mu-Xiang Chen, Yan Li, Lu-Min Hu, Lili Zhao, Zhenhua Jia, Xuefei Zhao, Xu-Hong Hu

2023-11-23 Research Article

DOI: 10.1039/D3QO01617J

Back cover

2024-01-16 Cover

DOI: 10.1039/D4QO90008A

Correction: An efficient metal free synthesis of 2-aminobenzothiozoles – a greener approach

Ganesh Sambasivam, Govindarajulu Gavara, Ramraj S, Gaikwad Rajendra, Karthikeyan Sivashanmugam

2023-11-02 Correction

DOI: 10.1039/D3OB90143B

An electrochemical method for direct sulfonylation of BODIPYs under green conditions

Zhuo Chen, Chen Li, Kui Liu, Li-Rong Wen, Ming Li, Lin-Bao Zhang

2023-12-01 Research Article

DOI: 10.1039/D3QO01616A

Photoredox-catalyzed intramolecular oxy- and aminoacylation of alkenes with acyl oxime esters: facile synthesis of acylated saturated heterocycles

Min Wang, Liang-Chen Ren, Yu-Rui Jian, Xin-Yu Fu, Hong-Yu Zheng, Xiao Zha

2023-11-17 Research Article

DOI: 10.1039/D3QO01659E

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

Chemical Communications

Chemical Communications
CiteScore: 8.6
Self-citation Rate: 4.7%
Articles per Year: 2458

ChemComm publishes urgent research which is of outstanding significance and interest to experts in the field, while also appealing to the journal’s broad chemistry readership. Our communication format is ideally suited to short, urgent studies that are of such importance that they require accelerated publication. Our scope covers all topics in chemistry, and research at the interface of chemistry and other disciplines (such as materials science, nanoscience, physics, engineering and biology) where there is a significant novelty in the chemistry aspects. Major topic areas covered include: Analytical Chemistry Catalysis Chemical Biology and medicinal chemistry Computational Chemistry and Machine Learning Energy and sustainable chemistry Environmental Chemistry Green Chemistry Inorganic Chemistry Materials Chemistry Nanoscience Organic Chemistry Physical Chemistry Polymer Chemistry Supramolecular 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.