Three Different Dimerizations of 2-Bromo-3-methyl-1,4-naphthoquinones
- Shuhei Azuma ,
- Kazuyuki Nishio ,
- Konomi Kubo ,
- Takahiro Sasamori ,
- Norihiro Tokitoh ,
- Kouji Kuramochi , and
- Kazunori Tsubaki
View Author Information
† Graduate School for Life and Environmental Sciences, Kyoto Prefectural University, 1-5 Shimogamo Hangi-cho, Sakyo-ku, Kyoto 606-8522, Japan
‡ Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
*(K.K.) Tel and Fax: +81-75-703-5603. E-mail: [email protected]. (K.T.) Tel and Fax: +81-75-703-5902. E-mail: [email protected]
Abstract
Three types of dimeric naphthoquinones, which possess structurally diverse skeletons, can be prepared in one step from 2-bromo-3-methyl-1,4-naphthoquinones. 2,2′-Dimeric naphthoquinones were prepared by a one-pot Stille-type reaction via vinylstannanes. Oxepines are formed by unexpected domino reactions via 1,4-dihydroxynaphthalene species. Epoxides are formed by a Michael/Darzens reaction via the o-quinone methides.
Cited By
This article is cited by 14 publications.
- Vishwajeet Jha, Navneet Goyal, Cheryl K. Stevens, Edwin Stevens, and Jayalakshmi Sridhar . Synthetic Method to Form 2,2′-Bis(naphthoquinone) Compounds. The Journal of Organic Chemistry 2017, 82 (24) , 13686-13692. https://doi.org/10.1021/acs.joc.7b02501
- Motohiro Ota, Takahiro Sasamori, Norihiro Tokitoh, Takefumi Onodera, Yoshiyuki Mizushina, Kouji Kuramochi, and Kazunori Tsubaki . Synthesis, Photochemical Properties, and Cytotoxicities of 2H-Naphtho[1,2-b]pyran and Its Photodimers. The Journal of Organic Chemistry 2015, 80 (11) , 5687-5695. https://doi.org/10.1021/acs.joc.5b00645
- Mai Onuki, Motohiro Ota, Shoya Otokozawa, Shogo Kamo, Shusuke Tomoshige, Kazunori Tsubaki, Kouji Kuramochi. Dimerizations of 2-bromo-3-methyl-1,4-naphthoquinone and 2-methyl-1,4-naphthoquinone in tetra-n-butylammonium bromide. Tetrahedron 2020, 76 (6) , 130899. https://doi.org/10.1016/j.tet.2019.130899
- Dattatray Chadar, Dipali N. Lande, Shridhar P. Gejji, Milind D. Nikalje, Debamita Chakravarty, Sunita Salunke-Gawali. Trimerization of Vitamin K3: Molecular structure and density functional theoretic investigations. Journal of Molecular Structure 2019, 1188 , 196-204. https://doi.org/10.1016/j.molstruc.2019.03.082
- Shogo Kamo, Kouji Kuramochi, Kazunori Tsubaki. Recent topics in total syntheses of natural dimeric naphthoquinone derivatives. Tetrahedron Letters 2018, 59 (3) , 224-230. https://doi.org/10.1016/j.tetlet.2017.12.040
- K. Thomas Finley. Quinones. 2016,,, 1-67. https://doi.org/10.1002/0471238961.1721091406091412.a02.pub3
- . Kirk-Othmer Encyclopedia of Chemical Technology. 2000,,https://doi.org/
- Shuhei Azuma, Motohiro Ota, Akito Ishida, Katsuhiro Isozaki, Hikaru Takaya, Masaharu Nakamura, Takahiro Sasamori, Norihiro Tokitoh, Kouji Kuramochi, Kazunori Tsubaki. Dimerization Reactions of 2-Bromo-3,5,6-trimethyl-1,4-benzoquinone. Chemistry Letters 2013, 42 (12) , 1531-1533. https://doi.org/10.1246/cl.130781
- Tien-Yau Luh, Lung-Lin Shiu, Sue-Min Yeh, Timothy T. Wenzel, Chin-Fa Lee, Tien-Yau Luh. Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II). 2013,,https://doi.org/10.1002/047084289X.rd098.pub2
- . Encyclopedia of Reagents for Organic Synthesis. 2001,,https://doi.org/
- John H. Ryan, Christopher Hyland, Jeremy Just, Adam G. Meyer, Jason A. Smith, Charlotte C. Williams. Seven-Membered Rings. 2013,,, 455-495. https://doi.org/10.1016/B978-0-08-099406-2.00017-0
- . . 2013,,https://doi.org/
- Maddali L. N. Rao, Somnath Giri. Pd-catalyzed threefold arylations of mono, di and tetra-bromoquinones using triarylbismuth reagents. RSC Advances 2012, 2 (33) , 12739. https://doi.org/10.1039/c2ra22058j
- Sambasivarao Kotha, Venu Srinivas, Nimita G. Krishna. DIVERSITY ORIENTED APPROACH TO 9-ARYL-SUBSTITUTED NAPHTHOXEPINE DERIVATIVES VIA CLAISEN REARRANGEMENT, RING-CLOSING METATHESIS AND SUZUKI–MIYAURA CROSS-COUPLING AS KEY STEPS. HETEROCYCLES 2012, 86 (2) , 1555. https://doi.org/10.3987/COM-12-S(N)89