4921-49-7Relevant articles and documents
Functionalization Including Fluorination of Caffeine, Guanosine Tetraacetate, and Uridine Triacetate using Electrochemical Oxidation
Sono, Masakazu,Toyoda, Naoko,Shizuri, Yoshikazu,Tori, Motoo
, p. 9237 - 9238 (1994)
The title compounds have been subjected to electrochemical oxidation with Et3N-3HF as an electrolyte.Caffeine afforded 8-fluorocaffeine as a sole product in 43percent yield.Guanosine tetraacetate and uridine triacetate gave the fluorinated compounds in 7.3 and 4.8 percent yield, respectively.Similar electrochemical oxidation of caffeine with methanol, KCl or KCN yielded 8-methoxycaffeine, 8-chlorocaffeine, or 8-cyanocaffeine, respecticvely.
8 - Aryloxy alkoxy substituted xanthine derivative as well as preparation method and application thereof
-
Paragraph 0036-0040; 0047-0050; 0057-0060; 0067-0070; ..., (2021/09/08)
8 - Aryloxy alkoxy substituted xanthine derivatives as well as a preparation method and application thereof are disclosed. The xanthine derivative is substituted with 8 - chlorine as a starting material and is substituted by nucleophilic substitution. The synthesis method has the advantages of few reaction steps, simple and mild conditions, simple operation and high yield. The compound of the invention has the structural formula shown in the general formula I. The compound has a certain control effect on lepidoptera pests such as diamondback moth and oriental armyworm. At the same time, plant pathogenic fungi such as tomato early blight germ, capsici, rape sclerotiorum, cucumber Botrytis cinerea, apple wheel grain germs and wheat sheath blight bacteria have high inhibition activity. The method is suitable for comprehensive control of insect pests and germs on various crops.
Synthetic Transformations of Sesquiterpene Lactones. 11.* Conjugates Based on Caffeine and Eudesmanolides with N-Containing Linkers
Reshetnikov,Patrushev,Shults
, p. 855 - 860 (2020/09/21)
8-(Aminoalkylamino)caffeine or 8-(piperazinyl)caffeine were formed in high yields by reacting 8-bromo- or 8-chlorocaffeine with linear and cyclic diamines using microwave-assisted organic synthesis. These amines were highly reactive in Michael reactions with sesquiterpene lactones containing active methylene groups. Conjugates with caffeine and eudesmanolide moieties bonded by a N-containing linker were synthesized.
Site-Selective C–H Functionalization of (Hetero)Arenes via Transient, Non-symmetric Iodanes
Fosu, Stacy C.,Hambira, Chido M.,Chen, Andrew D.,Fuchs, James R.,Nagib, David A.
supporting information, p. 417 - 428 (2019/02/14)
Fosu, Hambira, and colleagues describe the direct C–H functionalization of medicinally relevant arenes or heteroarenes. This strategy is enabled by transient generation of reactive, non-symmetric iodanes from anions and PhI(OAc)2. The site-selective incorporation of Cl, Br, OMs, OTs, and OTf to complex molecules, including within medicines and natural products, can be conducted by the operationally simple procedure included herein. A computational model for predicting site selectivity is also included. The discovery of new medicines is a time- and labor-intensive process that frequently requires over a decade to complete. A major bottleneck is the synthesis of drug candidates, wherein each complex molecule must be prepared individually via a multi-step synthesis, frequently requiring a week of effort per molecule for thousands of candidates. As an alternate strategy, direct, post-synthetic functionalization of a lead candidate could enable this diversification in a single operation. In this article, we describe a new method for direct manipulation of drug-like molecules by incorporation of motifs with either known pharmaceutical value (halides) or that permit subsequent conversion (pseudo-halides) to medicinally relevant analogs. This user-friendly strategy is enabled by combining commercial iodine reagents with salts and acids. We expect this simple method for selective, post-synthetic incorporation of molecular diversity will streamline the discovery of new medicines. A strategy for C–H functionalization of arenes and heteroarenes has been developed to allow site-selective incorporation of various anions, including Cl, Br, OMs, OTs, and OTf. This approach is enabled by in situ generation of reactive, non-symmetric iodanes by combining anions and bench-stable PhI(OAc)2. The utility of this mechanism is demonstrated via para-selective chlorination of medicinally relevant arenes, as well as site-selective C–H chlorination of heteroarenes. Spectroscopic, computational, and competition experiments describe the unique nature, reactivity, and selectivity of these transient, unsymmetrical iodanes.
