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Journal : Jurnal Sains Teh dan Kina

Synthesis of quinine N-oxide and an NMR tutorial in its structure determination Aisyah, Aisyah; Tamaela, Nila Berghuis; Santoso, Joko; Syah, Yana Maolana; Mujahidin, Didin
Jurnal Penelitian Teh dan Kina Vol 17, No 1 (2014)
Publisher : Research Institute for Tea and Cinchona

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (637.555 KB) | DOI: 10.22302/pptk.jur.jptk.v17i1.45

Abstract

Cinchona alkaloids are one of abundant natural chiral pool for organocatalysts. The application of an N-oxide group containing molecule in asymmetric reaction is currently wide developed. The structure of quinine consist two amine groups that could be oxidized to the N-oxide groups at N-1’ of quinoline and at N-1 of quinuclidine moieties. The oxidation reaction took place selectively at quinuclidine moiety by controlling the concentration of oxidizing agents. In this study we showed that N-1-oxide quinine could be occurred chemo­selectively by using a low concentration of ozone thana palladium catalyzed oxidation. The structure of products N1-oxide quinine was elucidated by spectroscopy data including 1H-NMR, 13C-NMR, 2D-NMR, infra-red and mass spectrometry. The developed method is a chemoselectively and eco-friendly method for synthesis N1-oxide quinine.
Synthesis of quinine N-oxide and an NMR tutorial in its structure determination Aisyah Aisyah; Nila Berghuis Tamaela; Joko Santoso; Yana Maolana Syah; Didin Mujahidin
Jurnal Penelitian Teh dan Kina Vol 17 No 1 (2014)
Publisher : Research Institute for Tea and Cinchona

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22302/pptk.jur.jptk.v17i1.45

Abstract

Cinchona alkaloids are one of abundant natural chiral pool for organocatalysts. The application of an N-oxide group containing molecule in asymmetric reaction is currently wide developed. The structure of quinine consist two amine groups that could be oxidized to the N-oxide groups at N-1’ of quinoline and at N-1 of quinuclidine moieties. The oxidation reaction took place selectively at quinuclidine moiety by controlling the concentration of oxidizing agents. In this study we showed that N-1-oxide quinine could be occurred chemo­selectively by using a low concentration of ozone thana palladium catalyzed oxidation. The structure of products N1-oxide quinine was elucidated by spectroscopy data including 1H-NMR, 13C-NMR, 2D-NMR, infra-red and mass spectrometry. The developed method is a chemoselectively and eco-friendly method for synthesis N1-oxide quinine.
Co-Authors A.A. Ketut Agung Cahyawan W Achmad Saifuddin Noer Affrida Affrida Aisyah Aisyah Aisyah Aisyah Alan Jefferson Aliefman Hakim Asep Aripin Asep Kadarohman Azzania Fibriani Bambang Ariwahjoedi Buchari Buchari Buchari Buchari Bunbun Bundjali Deana Wahyuningrum Debbie Soefie Soefie Dessy Natalia Devitri Amisa Dian Nugraheni Didin - Mujahidin Didin Mujahidin Didin Mujahidin Didin Mujahidin Didin Mujahidin Didin Mujahidin Didin Mujahidin Didin Mujahidin Dikhi Firmansyah Eliza Eliza Elvira Hermawati Elvira Hermawati Emilia L Ghisalberti Emilia L. Ghisalberti Emilio L Ghisalberti Endang Rosdiana Eri Bachtiar Eri Bakhtiar Euis Holishotan Hakim Euis Holisotan Hakim Euis Holisotan Hakim Euis Holisotan Hakim Euis Holisotan Hakim Euis Holisotan Hakim Euis Holisotan Hakim Euis Holisotan Hakim Euis Holisotan Hakim Euis Holisotasn Hakim Feraliana Feraliana Ferlinahayati Ferlinahayati Firdaus, Firdaus Hanapi Usman Hartiwi Diastuti Hartiwi Diastuti Hartiwi Diastuti Haryoto Haryoto Hendra Helmanto Hernandi Sujono Hiromitsu Takayama Hiromitsu Takayama I Dewa Agung Panji Dwipayana I Nyoman Adi Winata Ihsanawati Ihsanawati Ikram M. Said Ilim Ilim Ilimu, Edi Iqbal M. Choudhary Jalifah Latip Jalifah Latip Joko Santoso Kholifatu Rosyidah Laily Bin Din Lia Dewi Juliawati Lia Dewi Juliawati Lia Dewi Juliawaty Lia Dewi Juliawaty Lia Dewi Juliawaty Liliasari Liliasari Lukman Makmur Lukman Makmur Lukman Makmur Lukman Makmur Lukman Makmur Lukman Makmur M I Choudhary Marc Jeannin Mariko Katajima Mariko Kitajima Mariko Kitajima Marlia Singgih Marlia Singgih Marlia Singgih Masatake Niwa Melina Melina Muhamad Abdulkadir Martoprawiro Muhammad N. Jalaluddin Muhtadi Muhtadi Nanik Siti Aminah Nia Sri Hardianti Nila Berghuis Tamaela Nila Berghuis Tamaela, Nila Berghuis Nizar Happyana Nizar Happyana Nordin Hj Lajis Norio Aimi Norio Aimi Norio Aimi Noviany Noviany Nunuk H Soekamto Nunuk Hariani Soekamto Purkan Purkan Reza Aditama Rusjdi Tamin Sadijah Achmad Sahidin . Sahidin Sahidin Senadi Budiman Siti Nurbayti Siti Zubaidah Sjamsul Arifin Achmad Sjamsul Arifin Achmad Sjamsul Arifin Achmad Sjamsul Arifin Achmad Sjamsul Arifin Achmad Sjamsul Arifin Achmad Sjamsul Arifin Achmad Sjamsul Arifin Achmad Soerya Dewi Marliyana Sri Atun Suci Zulaikha Hildayani Sukrido Sukrido Suwandri Suwandri Suwandri Suwandri Tia Setiawati Tjodi Harlim Tri Cahyanto Valentina Adimurti Valentina Adimurti Kusumaningtyas Wasinton Simanjuntak Windayani, Neneng Yaya Rukayadi Yuliana, Trisna Zakaria Zakaria