113305-56-9Relevant articles and documents
Facile synthesis of 6-hydroxyindole-3-acetic acid: On the structure of the aromatic subunit of nephilatoxin-1~6
Shinada, Tetsuro,Miyachi, Miki,Itagaki, Yasuhiro,Naoki, Hideo,Yoshihara, Kazuo,Nakajima, Terumi
, p. 7099 - 7102 (1996)
A facile synthesis of 6-hydroxyindole-3-acetic acid 1a, which is the proposed aromatic subunit of NPTX-1~6, is described. Radical cyclization of isonitrile 2 successfully afforded 9 in high yield. The aromatic subunit of NPTX-1~6 was confirmed as 4-hydroxyindole-3-acetic acid 12 by comparison of the 1H-NMR spectra with those of authentic 4- and 6-hydroxyindole-3-acetic acids.
Oxidative Approach Enables Efficient Access to Cyclic Azobenzenes
Maier, Martin S.,Hüll, Katharina,Reynders, Martin,Matsuura, Bryan S.,Leippe, Philipp,Ko, Tongil,Sch?ffer, Lukas,Trauner, Dirk
supporting information, p. 17295 - 17304 (2019/11/03)
Azobenzenes are versatile photoswitches that have found widespread use in a variety of fields, ranging from photopharmacology to the material sciences. In addition to regular azobenzenes, the cyclic diazocines have recently emerged. Although diazocines have fascinating conformational and photophysical properties, their use has been limited by their synthetic accessibility. Herein, we present a general, high-yielding protocol that relies on the oxidative cyclization of dianilines. In combination with a modular substrate synthesis, it allows for rapid access to diversely functionalized diazocines on gram scales. Our work systematically explores substituent effects on the photoisomerization and thermal relaxation of diazocines. It will enable their incorporation into a wide variety of functional molecules, unlocking the full potential of these emerging photoswitches. The method can be applied to the synthesis of a new cyclic azobenzene with a nine-membered central ring and distinct properties.
Synthetic study on tetrapetalones: Stereoselective cyclization of N-acyliminium ion to construct substituted 1-benzazepines
Cheng, Li,Xlnyu, L.I. And,Ran, Hong
supporting information; experimental part, p. 4036 - 4039 (2009/12/09)
The synthesis of the tetracyclic core of complex antibiotic tetrapetalones has been achieved In three steps starting from the simple Intermediate γ-hydroxy amide, which can be accessed through a high-yielding six-step sequence. The successful synthesis relies on a novel strategy based on the N-acyliminium ion cyclizatlon.
