Metal-free annulation/aerobic oxidative dehydrogenation of cyclohexanones with o-acylanilines: efficient syntheses of acridines

Green Chem., 2016, Advance Article
DOI: 10.1039/C6GC02396G, Communication

Gopal Chandru Senadi, Ganesh Kumar Dhandabani, Wan-Ping Hu, Jeh-Jeng Wang
We have identified metal-free reaction conditions for the annulation/aerobic oxidative dehydrogenation of cyclohexanones with o-acylanilines to the corresponding acridine derivatives.

Metal-free annulation/aerobic oxidative dehydrogenation of cyclohexanones with o-acylanilines: efficient syntheses of acridines

Metal-free annulation/aerobic oxidative dehydrogenation of cyclohexanones with o-acylanilines: efficient syntheses of acridines

Gopal Chandru Senadi,^a   Ganesh Kumar Dhandabani,^a  Wan-Ping Hu^b and   Jeh-Jeng Wang*^a  

*Corresponding authors

^aDepartment of Medicinal and Applied Chemistry, Kaohsiung Medical University, No. 100, Shiquan 1st Rd, Sanmin District, Kaohsiung City, Taiwan
E-mail: jjwang@kmu.edu.tw

^bDepartment of Biotechnology, Kaohsiung Medical University, No. 100, Shiquan 1st Rd, Sanmin District, Kaohsiung City, Taiwan

Green Chem., 2016, Advance Article

DOI: 10.1039/C6GC02396G, 

http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C6GC02396G?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

Gopal Chandru Senadi

Kaohsiung Medical University

Department of Medicinal and Applied Chemistry

Kaohsiung, Taiwan

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We have identified metal-free reaction conditions for the annulation/aerobic oxidative dehydrogenation of cyclohexanones with o-acylanilines to the corresponding acridine derivatives. The combination of trifluoroacetic acid (TFA), tert-butyl hydroperoxide (TBHP), dimethylsulfoxide (DMSO) and oxygen (O₂) converted the cyclohexanone derivatives to an aromatic aryl product in moderate to good yields. The experimental results suggest that this process involves an aza-allyl oxidation intermediate.

Prof. Jeh-Jeng Wang

Professor
Department of Medicinal and Applied Chemistry
Kaohsiung Medical University
Kaohsiung, Taiwan

Lab: N842, Bioorganic chemistry Laboratory
Email: jjwang@kmu.edu.tw
Tel: +886-7-3121101
Fax: 886-7-3125339

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Prof. Jeh-Jeng Wang

Education: B.S., Chemistry, National Chung-Hsing University, Taiwan (1975-1979) Ph.D., Chemistry, The Ohio State University, USA (1983-1989) Career: Teaching Assistant, National Chung-Hsing University, Taiwan (1981-1983) Postdoctoral fellow, College of Pharmacy, University of Texas, Austin, USA (1989-1991) Associate Professor, Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Taiwan (1991-2001) Professor, Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Taiwan (since 2001)

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3aa as a pale yellow solid (234 mg, 92%); m.p. 181-182 ° C; IR (neat)max: 1362 cm -1; 1 H NMR (400 MHz, CDCl3) δ 8.31 (d, J = 8.8 Hz, 2H), 7.76 (ddd, J = 8.0, 6.8, 1.6 Hz, 2H), 7.72 (d, J = 8.8 Hz, 2H), 7.66 – 7.56 (m, 3H), 7.49 – 7.41 (m, 4H);

13C NMR (101 MHz, CDCl3) δ 148.66, 147.24, 135.85, 130.37, 129.96, 129.45, 128.40, 128.31, 12

1H NMR

 

13 c nmr

 

//////////Metal-free annulatio, erobic oxidative dehydrogenation, cyclohexanones, o-acylanilines, acridines

Prof. J.J. Wang birthday party - October 21, 2016


Department of Medicinal and Applied Chemistry
Kaohsiung Medical University





Kaohsiung, TAIWAN

Kaohsiung

Municipality in Taiwan

Kaohsiung is a massive port city in southern Taiwan. It's home to many skyscrapers, such as the 248m-tall Tuntex Sky Tower, and is known for its diversity of parks. Its focal point is the Love River, with walking paths and cafes along its banks, and cruise boats navigating its waters. Shopping options range from high-end malls to the Liuhe and Ruifeng night markets

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