33876-20-9Relevant academic research and scientific papers
Practical synthesis of (S)-pyrrolidin-2-yl-1H-tetrazole, incorporating efficient protecting group removal by flow-reactor hydrogenolysis
Franckevi?ius, Vilius,Knudsen, Kristian Rahbek,Ladlow, Mark,Longbottom, Deborah A.,Ley, Steven V.
, p. 889 - 892 (2006)
A practical, safe, high-yielding and efficient synthesis of (S)-pyrrolidin-2-yl-1H-tetrazole has been developed, which avoids the generation of ammonium azide in the cyclisation step and the use of a 9:1 acetic acid-water mixture as the solvent in the hydrogenation. The previously extended hydrogenolysis reaction time (three days) is now reduced to hours through the use of an H-Cube (a continuous-flow reactor employing a mixed hydrogen-liquid flow stream). Georg Thieme Verlag Stuttgart.
An expedient route to the tetrazole analogues of α-amino acids
Demko, Zachary P.,Sharpless, K. Barry
, p. 2525 - 2527 (2002)
(Matrix presented) Convenient conditions are described for the transformation of α-aminonitriles to the tetrazole analogues of α-amino acids. Refluxing the starting material in water/2-propanol at 80 °C with sodium azide and catalytic zinc bromide affords
Glycosylation mediated - BAIL in aqueous solution
Delacroix, Sébastien,Bonnet, Jean-Pierre,Courty, Matthieu,Postel, Denis,Van Nhien, Albert Nguyen
, p. 12 - 18 (2013/10/08)
The use of Br?nsted acid ionic liquid (BAIL) as a catalyst for the activation of unreactive and unprotected glycosyl donors has been demonstrated for the first time in aqueous solution.
USE OF AZIDES IN SYNTHESIS
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Page/Page column 16-26, (2012/03/11)
Described herein are inventive methods for synthesis of tetrazoles. In some embodiments, the method involves the use of a flow reactor. The methods provided herein are capable at being carried out in short reaction times, with high yields, with minimal side reactions, and/or with minimal chance of explosions caused by the presence of azides.
Enantioselective total synthesis of (S)-(+)-lennoxamine through asymmetric hydrogenation mediated by l-proline-tetrazole ruthenium catalyst
Mirabal-Gallardo, Yaneris,Piérola, Johanna,Shankaraiah, Nagula,Santos, Leonardo S.
scheme or table, p. 3672 - 3675 (2012/10/07)
A novel asymmetric synthetic strategy to prepare isoindolobenzazepine based lennoxamine alkaloid has been achieved in high ee% starting from 2-(benzo[d][1,3]dioxol-5-yl)ethanamine and 1-(chloromethyl)-2,3-dimethoxybenzene in 5 steps and with a 34% overall yield. The potentiality of this route involved the Bischler-Napieralsky cyclization that leads to tetracyclic indolinium skeleton, generation of chiral center through asymmetric hydrogen-transfer reaction employing l-proline-tetrazole as chiral ligand with Ru/Ir/Rh, and anodic oxidation as the key steps in the synthesis.
Safe and efficient tetrazole synthesis in a continuous-flow microreactor
Palde, Prakash B.,Jamison, Timothy F.
supporting information; experimental part, p. 3525 - 3528 (2011/05/04)
Safer flow: The synthesis of 5-substituted tetrazoles in flow (see scheme) is safe, efficient, scalable, requires no metal promoter, and uses a near-equimolar amount of NaN3, yet nonetheless displays a broad substrate scope. The hazards associated with HN3 are essentially eliminated, shock-sensitive metal azides such as Zn(N3)2 are avoided, and residual NaN3 is quenched in-line with NaNO 2. Copyright
Pyrrolidine amides of pyrazolodihydropyrimidines as potent and selective KV1.5 blockers
Lloyd, John,Finlay, Heather J.,Vacarro, Wayne,Hyunh, Tram,Kover, Alexander,Bhandaru, Rao,Yan, Lin,Atwal, Karnail,Conder, Mary Lee,Jenkins-West, Tonya,Shi, Hong,Huang, Christine,Li, Danshi,Sun, Huabin,Levesque, Paul
scheme or table, p. 1436 - 1439 (2010/07/02)
Design and synthesis of pyrazolodihydropyrimidines as KV1.5 blockers led to the discovery of 7d as a potent and selective antagonist. This compound showed atrial selective prolongation of effective refractory period in rabbits and was selected for clinical development.
Synthesis of substituted 5-(pyrrolidin-2-yl)tetrazoles and their application in the asymmetric Biginelli reaction
Wu, Yong-Yong,Chai, Zhuo,Liu, Xin-Yuan,Zhao, Gang,Wang, Shao-Wu
experimental part, p. 904 - 911 (2009/07/19)
A series of chiral substituted 5-(pyrrolidin-2-yl)tetrazoles have been synthesized and evaluated as organocatalysts for the asymmetric Biginelli reaction. The relationship between catalytic activity and the different catalyst structures is briefly discussed. By using the optimized catalyst C10 (10 mol-%), a series of 3,4-dihydropyrimidin-2(1H)-one (DHPM) derivatives have been obtained in 63-88% yields and 68-81 % ee values within 24 h at room temperature.
1,3-Dipolar cycloaddition: Click chemistry for the synthesis of 5-substituted tetrazoles from organoaluminum azides and nitriles
Aureggi, Valentina,Sedelmeier, Gottfried
, p. 8440 - 8444 (2008/09/19)
Cheap and safe: Conventional methods to prepare tetrazoles employ dangerous, toxic reagents. A new route to these heterocycles (see scheme) uses inexpensive and nontoxic dialkyl aluminum azides. The cycloaddition occurs under mild conditions and tolerates a variety of functional groups. The low cost and ecocompatibility make this process attractive for large-scale preparation. (Chemical Equation Presented).
PDF INHIBITORS
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Page/Page column 34, (2010/11/28)
The invention relates to novel compounds that are inhibitors of peptidyl deformylase (PDF). The compounds are useful as antimicrobials and antibiotics. The compounds of the invention display selective inhibition of peptidyl deformylase versus other metalloproteinases such as MMPs. Methods of preparation and uses of the compounds are also disclosed.
