Involving the Generation of Two Bonds 5.1. Introduction 5.2. Formation of the NÀC 2 and C 3 ÀC 4 Bonds 5.2.1. DielsÀAlder Related Reactions 5.2.2. Tandem Michael AdditionÀCyclization Sequence 5.2.3. Miscellaneous Reactions 5.3. Formation of the NÀC 2 and C 4 ÀC 4a Bonds 5.3.1. Michael Addition Initiated Reactions 5.3.2. Miscellaneous Reactions 5.4. Formation of the NÀC 2 and C 2 ÀC 3 Bonds 5.5. Formation of the C 2 ÀC 3 and C 3 ÀC 4 Bonds 5.6. Formation of the C 2 ÀC 3 and C 4 ÀC 4a Bonds 5.7. Formation of the C 3 ÀC 4 and C 4 ÀC 4a Bonds 5.8. Formation of the C 8a ÀN and C 4 ÀC 4a Bonds 5.9. Formation of the NÀC 2 and C 8a ÀN Bonds 6. Synthesis of 1,2,3,4-Tetrahydroquinolines Involving the Generation of Three or More Bonds 6.1. Formation of the NÀC 2 , C 2 ÀC 3 , and C 4 ÀC 4a Bonds: The Povarov and Related Reactions
Tetrahydroquinoline is one of the
most important simple nitrogen
heterocycles, being widespread in nature and present in a broad variety
of pharmacologically active compounds. This Review summarizes the
progress achieved in the chemistry of tetrahydroquinolines, with emphasis
on their synthesis, during the period from mid-2010 to early 2018.
A mild and efficient methodology for the synthesis of oxygenated carbazoles from diarylamines under non-acidic conditions was developed, based on a palladium-catalyzed, microwave-assisted double C-H bond activation process. This new protocol was successfully applied to the synthesis of three naturally occurring carbazoles, namely murrayafoline
More than 80% of chronic infections of bacteria are caused by biofilms. It is also a long-term survival strategy of the pathogens in a nonhost environment. Several amphiphilic molecules have been used in the past to potentially disrupt biofilms; however, the involvement of multistep synthesis, complicated purification and poor yield still remains a major problem. Herein, we report a facile synthesis of glycolipid based surfactant from renewable feedstocks in good yield. The nature of carbohydrate unit present in glycolipid influence the ring chain tautomerism, which resulted in the existence of either cyclic structure or both cyclic and acyclic structures. Interestingly, these glycolipids self-assemble into gel in highly hydrophobic solvents and vegetable oils, and displayed foam formation in water. The potential application of these self-assembled glycolipids to disrupt preformed biofilm was examined against various pathogens. It was observed that glycolipid 6a disrupts Staphylococcus aureus and Listeria monocytogenes biofilm, while the compound 6c was effective in disassembling uropathogenic E. coli and Salmonella enterica Typhimurium biofilms. Altogether, the supramolecular self-assembled materials, either as gel or as surfactant solution could be potentially used for surface cleansing in hospital environments or the food processing industries to effectively reduce pathogenic biofilms.
The use of cerium(IV) ammonium nitrate as a catalyst of the Friedländer reaction allows the synthesis of polysubstituted quinoline derivatives in excellent yields, avoiding the traditional harshly basic or acidic conditions. Unlike most other previously known reagents, CAN allows double condensations and is also an excellent catalyst for the Borsche variation of the Friedländer reaction, which has been applied to the very efficient synthesis of the antitumor alkaloid luotonin A.
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