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2024

Gold-Catalyzed Heteroannulation of Anthranilic Acids with Alkynes: Synthesis of 3,1-Benzoxazin-4-ones

Masahiro Abe,* Mai Takano, Akiho Mizukami, Tetsutaro Kimachi, Kiyofumi Inamoto*

The Journal of Organic Chemistry, accepted for publication, 2024


Palladium-Catalyzed Heteroannulation of Salicylamides with Propargyl Carbonates: Synthesis of 1,4-Benzoxazepin-5-ones

Masahiro Abe,* Megumu Kawamoto, Akiho Mizukami, Tetsutaro Kimachi, Kiyofumi Inamoto*

The Journal of Organic Chemistry, 89(14), 10037-10046, 2024


Chlorobenzene-driven palladium-catalysed lactonisation of benzoic acids

Masahiro Abe,* Akiho Mizukami, Emi Yoshida, Tetsutaro Kimachi, Kiyofumi Inamoto*

RSC Advances, 14(2), 808-811, 2024




2023

Synthesis of Aliphatic Nitriles via Desulfonylative Smiles Rearrangement

Masahiro Abe,* Honoka Jitsumatsu, Mikoto Araki, Akiho Mizukami, Tetsutaro Kimachi, Kiyofumi Inamoto*

Synthesis, 55(19), 3121-3128, 2023



2022

Gold(I)-Catalyzed Heteroannulation of Salicylic Amides with Alkynes: Synthesis of 1,3-Benzoxazin-4-one Derivatives

Masahiro Abe,* Megumu Kawamoto, Mayu Inoue, Tetsutaro Kimachi, Kiyofumi Inamoto*

Organic Letters, 24(31), 5684-5687, 2022


Site-Selective Iodine Atom Transfer in Fluorinated Alkyl Iodides via 1,5-Hydrogen Atom Transfer

Masahiro Abe,* Yuka Yokoi, Aoi Hirata, Yumeno Matsuoka, Tetsutaro Kimachi, Kiyofumi Inamoto*

Chemical Communications, 58(53), 7416-7418, 2022


Nitrile Synthesis via Desulfonylative−Smiles Rearrangement

Masahiro Abe,* Sayasa Nitta, Erina Miura, Tetsutaro Kimachi, Kiyofumi Inamoto*

The Journal of Organic Chemistry, 87(6), 4460-4467, 2022



2021

Palladium-Catalyzed Dehydrogenative C–H Cyclization for Isoindolinone Synthesis

Masahiro Abe,* Kaho Ueta, Saki Tanaka, Tetsutaro Kimachi, Kiyofumi Inamoto*

RSC Advances, 11(43), 26988-26991, 2021



2020

A Solvent-Dependent Chirality-Switchable Thia-Michael Addition to α,β-Unsaturated Carboxylic Acids Using a Chiral Multifunctional Thiourea Catalyst

Noboru Hayama, Yusuke Kobayashi, Eriko Sekimoto, Anna Miyazaki, Kiyofumi Inamoto, Tetsutaro Kimachi, Yoshiji Takemoto*

Chemical Science, 11(21), 5572-5576, 2020


2019

Evaluation of molecularly imprinted polymers for chlorpromazine and bromopromazine prepared by multi-step swelling and polymerization method -The application for the determination of chlorpromazine and its metabolites in rat plasma by column-switching LC

Kanae Nishimura, Noboru Okamuira, Tetsutaro Kimachi, Jun Haginaka*

Journal of Pharmaceutical and Biomedical Analysis, 174, 248-255, 2019

Retention and molecular-recognition mechanisms of molecularly imprinted polymers for promazine derivatives

Jun Haginaka*, Kanae Nishimura, Tetsutaro Kimachi, Kiyofumi Inamoto, Yoshiji Takemoto, Yusuke Kobayashi

Talanta, 205, 120149, 2019

Rhodium-catalyzed Synthesis of Benzo[b]thiophene-3-carboxamides via Cyclization of (ortho-Alkynyl)phenyl Sulfides in the Presence of Isocyanates

Akiho Mizugami, Maika Tsugita, Mako Shimora, Saki Tanaka, Noboru Hayama, Tetsutaro Kimachi, Kiyofumi Inamoto*

Chemistry Letters, 48(5), 12014, 2019

Catalytic asymmetric aza-Michael addition of fumaric monoacids with multifunctional thiourea / boronic acids

Kenichi Michigami, Hiroki Murakami, Takeru Nakamura, Noboru Hayama, Yoshiji Takemoto*

Organic&Biomolecular Chemistry, 17(9), 2331-2335, 2019

Inhibition of angiogenesis and tumor growth by a novel 1,4-naphthoquinone derivative

Hiroko Murata, Tomohiro Shinya, Mariko Sakanaka, Satoru Takahashi, Arisa Nishiuchi, Tokutaro Ogata, Noboru Hayama, Tetsutaro Kimachi, Kenichi Toda, Satoru Takahashi

Drug Development Research, 80(3), 395-402, 2019


2018

Construction of cyclic ether-fused tricyclic naphtoquinone derivatives by intramolecular cyclization reaction

Tokutaro Ogata, Tetsutaro Kimachi

Heterocycles, 97, 107-140, 2018

Mechanistic Insight into Asymmetric Hetero-Michael Addition of α,β-Unsaturated Carboxylic Acids Catalyzed by Multifunctional Thioureas

Noboru Hayama, Ryuta Kuramoto, Kazuya Nishibayashi, Yusuke Kobayashi, Yoshiji Takemoto*, Tamas Foldes, Imre Papai*

Journal of the American Chemical Society, 140 (38), 12216–12225, 2018

PET probe detecting non-small cell lung cancer susceptible to epidermal growth factor receptor tyrosine kinase inhibitor therapy

Akira Makino, Anna Miyazaki, Ayaka Tomoike, Masahiro Ono, Hiroyuki Kimura, Kenji Arimitsu, Masahiro Hirata, Yoshiro Ohmoto, Ryuichi Nishii et al.

Bioorganic&Medicinal Chemistry, 26 (8), 1609–1613 (2018)


2017

Copper-catalyzed intramolecular C-H amination: a new entry to substituted xanthine derivatives

Maki Shimizu, Noboru Hayama, Tetsutaro Kimachi, Kiyofumi Inamoto*

Synthesis, 49 (18), 4183-4190, 2017

Simultaneous functionalization and cyclization of 2-ethynylaniline derivatives to indoles

Hiroya Kou, Shin Itoh, Kiyofumi Inamoto, Hiroki Shigehisa, Takao Sakamoto

Heterocycles, 95, 920-933, 2017

(18)F-Labeled Pyrido[3,4-d]pyrimidiine as an Effective Prode for Imaging of L858R Mutant Epidermal Growth Factor Receptor

Hiroyuki Kimura, Haruka Okuda, Masumi Ishiguro, Kenji Arimitsu, Akira Makino, Ryuichi Nishii, Anna Miyazaki, Yusuke Yagi, Hiroyuki Watanabe et al.

ACS Medicinal Chemistry Letters, 8 (4), 418–422, 2017


2016

Unusual, chemoselective etherification of 2-hydroxy-1,4-naphthoquinone derivatives utilizing alkoxymethyl chlorides: scope, mechanism and application to the synthesis of biologically active natural product (±)-lantalucratin C

Tokutaro Ogata, Tomoyo Yoshida, Maki Shimizu, Manami Tanaka, Chie Fukuhara, Junko Ishii, Arisa Nishiuchi, Kiyofumi Inamoto, Tetsutaro Kimachi*

Tetrahedron, 72 (11), 1423–1432, 2016

Rhodium-Catalyzed Cyclization of 2-Ethynylanilines in the Presence of Isocyanates: Approach toward Indole-3-carboxamides

Akiho Mizukami, Yumi Ise, Tetsutaro Kimachi, Kiyofumi Inamoto*

Organic Letters, 18 (4), 748–751, 2016

Development of hemiacetal esterified levofloxacin to prevent chelation with metal-containing drugs

Toru Otori, Sumio Matzno, Atushi Kawase, Masahiro Iwaki, Tetsutaro Kimachi, Kenji Nishiwaki, William C. Figoni, Ryuta Tominaga, Mai Asahide, Mayumi Nishikata, Yoshikazu Ishii, Kenji Mathuyama*

Journal of Pharmacy and Pharmacology, 68 , 1527–1534, 2016

Chiral Intergrated Catalysts Composed of Bifunctional Thiourea and Arylboronic Acid: Asymmetric Aza-Michael Addition of α, β-Unsaturated Carboxylic Acids

Noboru Hayama, Takumi Azuma, Yusuke Kobayashi, Yoshiji Takemoto*

Chemical&Pharmaceutical Bulletin, 64(7) , 704-17, 2016

Palladiium-Catalyzed Highly Chemoselective Intramolecular C-H Aminocarbonylation of Phenethylamines to Six-Membered Benzolactams

Hiroshi Taneda, Yoshinori Kondo*, Kiyofumi Inamoto*

Organic Letters, 18(11) , 70-17, 2016


2015

Unusual O-Alkylation of 2-Hydroxy-1,4-naphthoquinone Utilizing Alkoxymethyl Chlorides

Tokutaro Ogata, Tomoyo Yoshida, Manami Tanaka, Chie Fukuhara, Maki Shimizu, Junko Ishii, Arisa Nishiuchi, Kiyofumi Inamoto, Tetsutaro Kimachi*

Chemical & Pharmaceutical Bulletin, 63, 485–488, 2015

The first enantioselective total synthesis of lantalucratin C and determination of its absolute configuration

Tokutaro Ogata, Manami Tanaka, Momoe Ishigaki, Maki Shimizu, Arisa Nishiuchi, Kiyofumi Inamoto, Tetsutaro Kimachi*

Tetrahedron, 71 (38), 6672–6680, 2015

Highly Enantioselective (−)-Sparteine-Mediated Lateral Metalation-Functionalization of Remote Silyl Protected ortho-Ethyl N,N-Dialkyl Aryl O-Carbamates

Jurg Fassler, J. Adam McCubbin, Anna Roglans, Tetsutaro Kimachi, Joshua W. Hollett, Roland W. Kunz, Michael Tinkl, Yousheng Zhang, Ruiyao Wang, Michae Campbell, Victor Snieckus

The Journal of Organic Chemistry, 80 (7), 3368–3386 (2015)

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2014

A diversity-oriented synthesis of caroverine derivatives via TEMPO-promoted aerobic oxidative C–N bond formation

Yusuke Kobayashi, Yusuke Suzuki, Tokutaro Ogata, Tetsutaro Kimachi, Yoshiji Takemoto*

Tetrahedron Letters, 55 (22), 3299–3301, 2014

Studies on the oxidative cyclization of 3-hydroxy-1,2,4-trialkoxynaphthalenes and synthetic application for the biologically active natural compound: rhinacanthone

Tokutaro Ogata, Misae Doe, Aya Matsubara, Eri Torii, Chiaki Nishiura, Arisa Nishiuchi, Yusuke Kobayashi, Tetsutaro Kimachi*

Tetrahedron, 70 (2), 502–509, 2014


2013

Total synthesis of (±)-lantalucratins A and B by CAN-mediated oxidative cyclization

Tokutaro Ogata, Yoshiko Sugiyama, Saki Ito, Kazuha Nakano, Eri, Torii, Arisa Nishiuch, Tetsutaro Kimachi*

Tetrahedron, 69, 10470–10476, 2013


2012

Catalytic Asymmetric Synthesis of (S)-Laudanosine by Hydroamination

Tokutaro Ogata, Tetsutaro Kimachi, Ken-ichi Yamada, Yasutomo Yamamoto, Kiyoshi Tomioka*

Heterocycles, 86, 469–485, 2012

Organocatalyzed Isomerization of α-Substituted Alkynoates into Trisubstituted Allenoates by Dynamic Kinetic Resolution

Tsubasa Inokuma, Masaya Furukawa, Yusuke Suzuki, Tetsutaro Kimachi, Yusuke Kobayashi, Yoshiji Takemoto*

ChemCatChem, 4 (7), 983–985, 2012


2011

Highly efficient synthesis of quinoxalinone-N-oxide via tandem nitrosation/aerobic oxidative C–N bond formation

Yusuke Kobayashi,* Mami Kuroda, Natsuki Toba, Mari Okada, Rie Tanaka, Tetsutaro Kimachi*

Organic Letters,13,6280–6283, 2011

Asymmetric total synthesis of biologically active (–)-dehydroiso-β-lapachone and the determination of its absolute configuration

Tetsutaro Kimachi,* Eri Torii, Yusuke Kobayashi, Misae Doe, Motoharu Ju-ichi

Chemical & Pharmaceutical Bulletin, 59, 753–756, 2011

An efficient construction of nitrogen-containing heterocycles utilizing CN functional groups and its application to the synthesis of natural products (Review)

Yusuke Kobayashi*

Yakugaku Zasshi, 131, 1037–1046, 2011

α-Dimethylaminomethylenation-induced Houben–Hoesch-type cyclization of cyanoacetanilides: A practical synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-ones

Yusuke Kobayashi,* Terue Nakatani, Rie Tanaka, Mari Okada, Eri Torii, Takashi Harayama, Tetsutaro Kimachi*

Tetrahedron, 67, 3457–3463, 2011

Regioselective ring-opening reaction of unsymmetrical 2,3-diaryl epoxides via catalytic hydrogenolysis with Pd(0)EnCatTM

Tetsutaro Kimachi,* Hiroyo Nagata, Yusuke Kobayashi, Kaori Takahashi, Eri Torii, Motoharu Ju-ichi

Synlett, (3), 365–368 (2011)

Synthetic studies of salinosporamide A through the intramolecular hydroamidation of alkynes

Haruhi Kamisaki, Yusuke Kobayashi, Tetsutaro Kimachi, Yoshizumi Yasui, Yoshiji Takemoto*

Journal of Organometallic Chemistry, 696, 42–45 (2011)


2010

Asymmetric Darzens-type epoxidation via chiral ammonium ylides

Hiroyo Kinoshita, Akiko Ihoriya, Motoharu Ju-ichi, Tetsutaro Kimachi*

Synlett, (15), 2330–2334 (2010)

Enantioselective reduction of ketones and imines catalyzed by (CN-Box)ReV–oxo complexes

Kristine A. Nolin, Richard W. Ahn, Yusuke Kobayashi, Joshua J. Kennedy-Smith, F. Dean Toste*

Chemistry – A European Journal, 16 (31), 9555–9562 (2010)

HTLV-1 basic leucine-zipper factor, HBZ, interacts with MafB and suppresses transcription through a Maf recognition element

Takayuki Ohshima,* Risa Mukai, Norie Nakahara, Jun Matsumoto, Osamu Isono, Yusuke Kobayashi, Satoru Takahashi, Kunitada Shimotohno

Journal of Cellular Biochemistry, 111 (1), 187–194 (2010)

Effects of sulfaphenazole derivatives on cardiac ischemia–reperfusion injury: association of cytochrome P450 activity and infarct size

Yasuhiro Ishihara, Masaya Sekine, Ai Hamaguchi, Yusuke Kobayashi, Takashi Harayama, Mikio Nakazawa, Norio Shimamoto*

Journal of Pharmacological Sciences, 113, 335 – 342 (2010)

Trifluoroacetylation-induced Houben−Hoesch-type cyclization of cyanoacetanilides: increased nucleophilicity of CN groups

Yusuke Kobayashi,* Kosuke Katagiri, Isao Azumaya and Takashi Harayama

The Journal of Organic Chemistry, 75 (8), 2741–2744 (2010)