- On the reaction of anthranilic acid with thionyl chloride: The actual structure of 'Kametani's sulfinamide anhydride'
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Despite previous reports, no sulfinamide anhydride is formed from the reaction of anthranilic acid with thionyl chloride, the actual product being 2-sulfinylaminobenzoyl chloride. This excludes iminoketene formation in the reactions of this activated form
- Garin,Merino,Orduna,Tejero,Uriel
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- Thioester-appended organosilatranes: Synthetic investigations and application in the modification of magnetic silica surfaces
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The present investigation discloses a series of new organosilicon derivatives (3a-k) tailored with substituted benzoic acid modules (1a-k) via thioesterification with 3-mercaptopropylsilatrane (MPS). Product formation was authenticated using elemental analyses and different spectroscopic methods comprising FT-IR, NMR [1H, 13C] and LC-MS (Q-TOF). Thereafter, complete structural elucidation of compounds 3c and 3f was achieved by the single crystal X-ray technique. Photo-electronic inspection of all compounds by UV-Vis spectroscopy revealed their sensitivity towards substitution patterns. In addition, this is the first time that the potential of a silatranyl moiety has been tested for the modification of a silica surface pre-decorated with a magnetite core. The synthesis was achieved through a facile methodology involving chemical bonding at each stage, which proceeded without any external surfactant or template. The course of the reaction was followed by FT-IR, UV-Vis, XRD, TEM, FESEM, EDX and TGA techniques. Furthermore, the hybrid nanomaterial possessed significant sensorial ability toward copper ions, which makes the present protocol favourable for the construction of a new class of chelating ligands with an in-built multifunctional nanodevice.
- Singh, Gurjaspreet,Rani, Sunita,Arora, Aanchal,Aulakh, Darpandeep,Wriedt, Mario
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p. 6200 - 6213
(2016/07/19)
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- Efficient syntheses of 2,3-disubstituted natural quinazolinones via iridium catalysis
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Natural products sclerotigenin, pegamine, deoxyvasicinone, mackinazolinone, and rutaecarpine were synthesized. Core quinazolinone structures were constructed via Ir catalysis. The Royal Society of Chemistry 2012.
- Fang, Jie,Zhou, Jianguang
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supporting information; experimental part
p. 2389 - 2391
(2012/04/11)
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- First total synthesis of (-)-Circumdatin H, a novel mitochondrial NADH Oxidase inhibitor
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An efficient and highly convergent synthesis of the mitochondrial NADH oxidase inhibitor (-)-circumdatin H is described. The strategy employs the intramolecular Eguchi aza-Wittig protocol as a key step to install the crucial central core BC ring system, leading to the first total synthesis of the target molecule. Georg Thieme Verlag Stuttgart · New York.
- Bose, D. Subhas,Chary, M. Venu
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experimental part
p. 643 - 650
(2010/04/30)
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- On the reaction of anthranilic acid with thionyl chloride: Iminoketene intermediate formation
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2-(Sulfinylamino) benzoyl chloride is formed on treating anthranilic acid with thionyl chloride. The formation of iminoketene intermediate from 2-(sulfinylamino) benzoyl chloride is established and the reactions carried out using the intermediate are described.
- Jacob, Dominic E.,Mathew, Lopez
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p. 664 - 668
(2008/09/18)
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- Synthesis and structure-activity relationships of vasicine analogues as bronchodilatory agents
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The series of vasicine (1) analogues, an alkaloid from Adhatoda vasica Nees., were synthesized with changes in A, B or C rings. Compounds 3-19 were evaluated for in vitro bronchodilatory activity using isolated guinea pig tracheal chain. Compounds 3-8 were also synthesized in good yields using microwave-mediated synthesis under solvent free conditions. Compounds 5 and 8 with seven-member C ring were more active than etofylline and caused 100% relaxation of both the histamine and acetylcholine pre-contracted guinea pig tracheal chain. The structure-activity relationship studies showed that the quinazoline and oxo functionalities were essential for activity. The compounds without C ring and instead having aliphatic and phenyl substitutions in B ring showed relaxation against histamine pre-contracted tracheal chain only, 2-methyl substituted analogues, 12 and 13, being most active with 100% relaxation effect. Birkhaeuser Boston 2006.
- Mahindroo, Neeraj,Ahmed, Zabeer,Bhagat, Asha,Bedi, Kasturi Lal,Khajuria, Ravi Kant,Kapoor, Vijay Kumar,Dhar, Kanaya Lal
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p. 347 - 368
(2007/10/03)
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- Total synthesis of the cytotoxic alkaloid luotonin A
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The structure of luotonin A was unambiguously confirmed by total synthesis. Deprotonation of 3-oxo-1H-pyrrolo[3,4-b]quinoline gave an anion which was coupled with 2-sulfinylaminobenzoyl chloride (prepared by reaction of anthranilic acid with thionyl chlor
- Wang, Haishan,Ganesan
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p. 9097 - 9098
(2007/10/03)
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- Synthesis of 2'- and 2''-O-Acylated Maltotriosides as Potential Fluorescence-quenched Substrates for α-Amylase
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Several 2'- and 2''-O-acylated maltotrioside derivatives have been prepared as substrates for use in fluorescence-quenched assays of α-amylase.These maltotriosides carry a quenching group at the reducing and a fluorescen
- Ferro, Vito,Meldal Morten,Bock, Klaus
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p. 2169 - 2176
(2007/10/02)
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