612825-76-0Relevant articles and documents
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.
Highly stereoselective 7-endo-trig /ring contraction cascade to construct pyrrolo[1,2- a ]quinoline derivatives
Li, Xinyu,Li, Cheng,Zhang, Wenjing,Lu, Xiang,Han, Shiqing,Hong, Ran
supporting information; experimental part, p. 1696 - 1699 (2010/09/05)
With the cooperation of Cram's phenonium ion, a novel cascade reaction was illustrated to construct pyrrolo[1,2-a]quinolines as a sole diastereoisomer in good to excellent yields. Preliminary mechanistic studies revealed that the γ-lactam ring and electron-rich arene are important driving forces for ring contraction.
Catalytic asymmetric synthesis of the central tryptophan residue of celogentin C
Castle, Steven L.,Srikanth
, p. 3611 - 3614 (2007/10/03)
(Equation presented) Chiral phase-transfer catalyst 5 containing an electron-deficient trifluorobenzyl moiety promoted the alkylation of glycine derivative 6 with propargyl bromide 7a in good yield and excellent ee. The resulting propargyl glycine 8 was c