Relevant bibliographies by topics / Azetidine synthesis

Contents

  1. Journal articles
  2. Dissertations / Theses
  3. Books
  4. Book chapters
  5. Conference papers

Academic literature on the topic 'Azetidine synthesis'

Author: Grafiati
Published: 4 June 2021
Last updated: 11 February 2022

Create a spot-on reference in APA, MLA, Chicago, Harvard, and other styles

Select a source type:

Consult the lists of relevant articles, books, theses, conference reports, and other scholarly sources on the topic 'Azetidine synthesis.'

Next to every source in the list of references, there is an 'Add to bibliography' button. Press on it, and we will generate automatically the bibliographic reference to the chosen work in the citation style you need: APA, MLA, Harvard, Chicago, Vancouver, etc.

You can also download the full text of the academic publication as pdf and read online its abstract whenever available in the metadata.

Journal articles on the topic "Azetidine synthesis"

1

Sun, Jian, Shan Shan Gong, and Qi Sun. "A Novel Strategy for the Synthesis of Azetidine." Advanced Materials Research 830 (October 2013): 135–38. http://dx.doi.org/10.4028/www.scientific.net/amr.830.135.

Full text
Abstract:
A novel method for the synthesis of azetidine via phosphoramidate intermediate has been developed. In the key step, cleavage of the PN bond in azetidin-1-ylphosporamidate with hydrochloric acid furnished a high-yielding conversion to azetidine hydrochloride.
APA, Harvard, Vancouver, ISO, and other styles
2

Nitta, Yoshihiro, and Yasuyuki Kanamori. "Synthesis of Azetidine from 1-Substituted Azetidin-3-ols." HETEROCYCLES 24, no. 9 (1986): 2467. http://dx.doi.org/10.3987/r-1986-09-2467.

Full text
APA, Harvard, Vancouver, ISO, and other styles
3

Peipiņš, Vilnis, Krista Suta, and Māris Turks. "Study on Synthesis of N-Protected 2-Triazolyl Azetidines." Key Engineering Materials 762 (February 2018): 19–24. http://dx.doi.org/10.4028/www.scientific.net/kem.762.19.

Full text
Abstract:
Azetidine derivatives are interesting scaffolds in terms of medicinal chemistry. They can be regarded as structural homologs of aziridines. Herein we report synthetic approach to the novel N-protected 2-triazolyl azetidines which are structurally similar to our previously described aziridine derivatives with matrix metalloproteinase-2 inhihbitory activities. The synthetic rout includes ring closing of ethyl 2,4-dibromobutanoate, selective reduction of ester to aldehyde and transformation of the latter to terminal alkyne by Ohira-Bestmann reagent. 2-Ethynyl azetidines as key intermediates were
APA, Harvard, Vancouver, ISO, and other styles
4

Duréault, Annie, Martine Portal, François Carreaux, and Jean Claude Depezay. "Synthesis of highly functionalized homochiral azetidines and azetidine-2-carboxylic esters." Tetrahedron 49, no. 20 (1993): 4201–10. http://dx.doi.org/10.1016/s0040-4020(01)85738-0.

Full text
APA, Harvard, Vancouver, ISO, and other styles
5

Tayama, Eiji, та Nobuhiro Nakanome. "Synthesis of optically active 2-substituted azetidine-2-carbonitriles from chiral 1-arylethylamine via α-alkylation of N-borane complexes". RSC Advances 11, № 38 (2021): 23825–37. http://dx.doi.org/10.1039/d1ra04585g.

Full text
APA, Harvard, Vancouver, ISO, and other styles
6

Jin, Jian Zhong, and Jie Zhang. "Synthesis of L-Azetidine-2-Carboxylic Acid." Advanced Materials Research 455-456 (January 2012): 635–38. http://dx.doi.org/10.4028/www.scientific.net/amr.455-456.635.

Full text
Abstract:
L-Azetidine-2-carboxylic acid, the first known example naturally occurring azetidine, was synthesized in a novel, simple, clean and improved procedure. It was synthesized from γ-butyrolactone through four steps: bromination and esterification, cyclization, hydrogenation and resolution. The overall yield could reach 13.2%.
APA, Harvard, Vancouver, ISO, and other styles
7

Hanessian, Stephen, and Jian-min Fu. "Total synthesis of polyoximic acid." Canadian Journal of Chemistry 79, no. 11 (2001): 1812–26. http://dx.doi.org/10.1139/v01-171.

Full text
Abstract:
The structure and stereochemistry of polyoximic acid, a degradation product of polyoxins, was originally designated as trans-3-ethylidene-L-azetidine-2-carboxylic acid. However, total synthesis revealed that the correct structure was in fact cis-3-ethylidene-L-azetidine-2-carboxylic acid, which was confirmed by X-ray crystallography. The synthesis of the trans-isomer was also done and its identity was confirmed by X-ray analysis as well. The key step for constructing the four-membered ring was a rhodium catalyzed carbenoid insertion into the N—H bond of a beta-amino acid derivative. The stereo
APA, Harvard, Vancouver, ISO, and other styles
8

Reidl, Tyler W., Jongwoo Son, Donald J. Wink, and Laura L. Anderson. "Facile Synthesis of Azetidine Nitrones and Diastereoselective Conversion into Densely Substituted Azetidines." Angewandte Chemie International Edition 56, no. 38 (2017): 11579–83. http://dx.doi.org/10.1002/anie.201705681.

Full text
APA, Harvard, Vancouver, ISO, and other styles
9

Reidl, Tyler W., Jongwoo Son, Donald J. Wink, and Laura L. Anderson. "Facile Synthesis of Azetidine Nitrones and Diastereoselective Conversion into Densely Substituted Azetidines." Angewandte Chemie 129, no. 38 (2017): 11737–41. http://dx.doi.org/10.1002/ange.201705681.

Full text
APA, Harvard, Vancouver, ISO, and other styles
10

Gavale, Kishor S., Shrawan R. Chavan, Ayesha Khan, Rakesh Joshi, and Dilip D. Dhavale. "Azetidine- and N-carboxylic azetidine-iminosugars as amyloglucosidase inhibitors: synthesis, glycosidase inhibitory activity and molecular docking studies." Organic & Biomolecular Chemistry 13, no. 23 (2015): 6634–46. http://dx.doi.org/10.1039/c5ob00668f.

Full text
APA, Harvard, Vancouver, ISO, and other styles
More sources

Dissertations / Theses on the topic "Azetidine synthesis"

1

Pearson, Christopher I. "Lithiated azetidine and azetine chemistry." Thesis, University of Oxford, 2014. http://ora.ox.ac.uk/objects/uuid:cf3c942f-80de-4092-a38d-11006ccbb9ce.

Full text
Abstract:
This work describes developments in new azetidine and azetine chemistry; specifically, methods developed for the introduction of functionality α- to nitrogen in both ring systems, with additionally in situ formation of the latter system, from azetidine substrates. Chapter 1 discusses the growing importance of azetidines, and the current methods available for making substituted azetidines by ring formation. Further discussion comprises of current sp<sup>3</sup> C–H activation approaches α- to nitrogen in heterocyclic compounds as potential methods for sp<sup>3</sup> C–H activation on azetidines
APA, Harvard, Vancouver, ISO, and other styles
2

Lenagh-Snow, Gabriel Matthew Jack. "The synthesis of azetidine and piperidine iminosugars from monosaccharides." Thesis, University of Oxford, 2012. http://ora.ox.ac.uk/objects/uuid:207235d5-2ea5-4724-92fd-924fa0ccd4ed.

Full text
Abstract:
Iminosugars are polyhydroxylated alkaloids, and can be generally defined as sugar mimetics in which the endocyclic oxygen atom has been replaced with a basic nitrogen. A common affect of this atomic substitution is to bestow these compounds with the ability to inhibit various sugarprocessing enzymes; most significantly the glycosidases (glycoside hydrolases) which areintimately involved in a huge array of biological functions. Compounds which inhibit these enzymes concordantly possess much potential as medicinal agents for the treatment of a variety of diseases. Several iminosugars have alread
APA, Harvard, Vancouver, ISO, and other styles
3

Cararas, Shaine A. "Synthesis and Biological Evaluation of Novel GBR 12909 Tropane and Azetidine Hybrid Analogues." ScholarWorks@UNO, 2007. http://scholarworks.uno.edu/td/565.

Full text
Abstract:
The high affinity, selective dopamine transporter ligand GBR 12909 has served as a template for the design of two novel classes of dopamine transporter ligands. A series of 3-[2- (diarylmethoxyethyidenyl)]-N-substituted tropane derivatives were synthesized and the binding affinities of these compounds were determined at the dopamine (DAT), serotonin (SERT) and norepinephrine (NET) transporters in rat brain tissue preparations. The tropane derivatives were found to exhibit more potent affinity and selectivity for DAT than GBR 12909. From the SAR of the tropane analogues and GBR 12909, a n
APA, Harvard, Vancouver, ISO, and other styles
4

Forsyth, Andrea N. "Synthesis and Biological Evaluation of Rigid Analogues of Methamphetamines." ScholarWorks@UNO, 2012. http://scholarworks.uno.edu/td/1436.

Full text
Abstract:
A series of rigid azetidenyl-based methamphetamine analogs were synthesized from commercially available N-Boc-azetidinone. The benzylideneazetidine analogs were prepared via a Wittig olefination via the ylides generated from the corresponding triphenylphosphonium benzylhalide salts. The substituted benzylazetidine analogs were synthesized from the corresponding benzylideneazetidienes via hydrogention over palladium and platinum catalysts. The benzylideneazetidine and benzyliazetidine analogs were evaluated at monoamine transporters as a part of preliminary structure-activity study for the deve
APA, Harvard, Vancouver, ISO, and other styles
5

Mortimer, Claire. "New transformations of azacycles." Thesis, University of Oxford, 2015. https://ora.ox.ac.uk/objects/uuid:1fe27dc8-6525-4d45-a398-b3e6531e7b99.

Full text
Abstract:
The work presented in this thesis involves new transformations of azacycles, focusing on the introduction of functionality &alpha;-to N. &alpha;-C-H functionalisation on an azetidine has been a long-standing challenge, with N-protecting/activating groups that work well in the higher and lower azacyclic systems not viable. A recent breakthrough in the Hodgson group showed the rarely used N-thiopivaloyl group was effective for &alpha;-deprotonation– electrophile trapping on azetidines, but was not without limitations concerning harsh removal conditions and scope for further substitutions. This
APA, Harvard, Vancouver, ISO, and other styles
6

Glawar, Andreas Felix Gregor. "Design, synthesis and biological evaluation of glycosidase inhibitors in an anti-cancer setting." Thesis, University of Oxford, 2013. http://ora.ox.ac.uk/objects/uuid:602edf26-d9ff-4fcf-8dec-c8548f3578da.

Full text
Abstract:
The aim of the work described in this thesis was to explore the synthesis of glycosidase inhibitors and to evaluate their potential as anti-cancer agents. Glycosidases catalyze the fission of glycosidic bonds and are involved in vital biological functions. With regard to their potential for anti-cancer therapy, two glycosidases were identified: α-N-acetyl-galactosaminidase and β-N-acetyl-hexosaminidase. The former has been implicated in causing immunosuppression in advanced cancer patients by negating the effect of the macrophage activating factor (MAF), while the latter is secreted by invadin
APA, Harvard, Vancouver, ISO, and other styles
7

Honcharenko, Dmytro. "Conformationally Constrained Nucleosides, Nucleotides and Oligonucleotides : Design, Synthesis and Properties." Doctoral thesis, Uppsala universitet, Bioorganisk kemi, 2008. http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-8887.

Full text
Abstract:
This thesis is based on six original research publications describing synthesis, structure and physicochemical and biochemical analysis of chemically modified oligonucleotides (ONs) in terms of their potential diagnostic and therapeutic applications. Synthesis of two types of bicyclic conformationally constrained nucleosides, North-East locked 1',2'-azetidine and North locked 2',4'-aza-ENA, is described. Study of the molecular structures and dynamics of bicyclic nucleosides showed that depending upon the type of fused system they fall into two distinct categories with their respective internal
APA, Harvard, Vancouver, ISO, and other styles
8

Yoshizawa, Akina. "Azetidines for asymmetric synthesis." Thesis, University of Birmingham, 2018. http://etheses.bham.ac.uk//id/eprint/8719/.

Full text
Abstract:
The creation of asymmetric ligands with lower environmental impact is important, as such chiral N,N' ligands attract some attention. A new method for the synthesis of 1,2,4-trisubstituted amino azetidines with \(cis\) relative configuration across its two stereogenic centres was reported in 2013. Due to this \(cis\) conformation, the azetidine compounds are expected to be good chiral ligands for asymmetric catalysis. The nitro aldol (Henry) reaction is an established method for producing new carbon-carbon bonds and is a key reaction in the synthesis of many important compounds. Enantioselectiv
APA, Harvard, Vancouver, ISO, and other styles
9

Thaxton, Amber. "Synthesis of Novel Azetidines." ScholarWorks@UNO, 2013. http://scholarworks.uno.edu/td/1764.

Full text
Abstract:
Azetidine is a four-membered nitrogen-containing heterocyclic ring that has recently received a great deal of attention as a molecular scaffold for the design and preparation of biologically active compounds. Structure-activity studies employing functionalized azetidines have led to the development of variety of drug molecules and clinical candidates encompassing a broad spectrum of biological activities. Herein, the synthesis a novel series of 3-aryl-3-arylmethoxyazetidines is described. Selected 3-aryl-3-arylmethoxyazetidines were evaluated for their binding affinity to multiple monoaminergi
APA, Harvard, Vancouver, ISO, and other styles
10

Varghese, Oommen P. "Conformationally Constrained Nucleosides : Design, Synthesis, and Biochemical Evaluation of Modified Antisense Oligonucleotides." Doctoral thesis, Uppsala : Acta Universitatis Upsaliensis, 2007. http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-8266.

Full text
APA, Harvard, Vancouver, ISO, and other styles
More sources

Books on the topic "Azetidine synthesis"

1

Toske, Steven Gerald. Part I: Synthesis of azetidin-2-ones from pyrazolidin-3-ones ; Part II : synthesis of a subunit of the immunosuppressant FK-506. 1993.

Find full text
APA, Harvard, Vancouver, ISO, and other styles

Book chapters on the topic "Azetidine synthesis"

1

Yoda, Hidemi, Masaki Takahashi, and Tetsuya Sengoku. "Azetidine and Its Derivatives." In Heterocycles in Natural Product Synthesis. Wiley-VCH Verlag GmbH & Co. KGaA, 2011. http://dx.doi.org/10.1002/9783527634880.ch2.

Full text
APA, Harvard, Vancouver, ISO, and other styles
2

Faigl, F., E. Kovács, G. Turczel, et al. "Novel Methods for the Stereoselective Synthesis of Oxetane, Azetidine and Pyrrolidine Derivatives." In IFMBE Proceedings. Springer Berlin Heidelberg, 2011. http://dx.doi.org/10.1007/978-3-642-23508-5_352.

Full text
APA, Harvard, Vancouver, ISO, and other styles
3

Taber, Douglass F. "Stereocontrolled C-N Ring Construction: The Pyne Synthesis of Hyacinthacine B 3." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0054.

Full text
Abstract:
Keiji Maruoka of Kyoto University found (Organic Lett. 2010, 12, 1668) that the diazo amide 1 derived from the Oppolzer sultam condensed with the imine 2 to give the aziridine 3 with high stereocontrol. Andrei K. Yudin of the University of Toronto observed (Angew. Chem. Int. Ed. 2010, 49, 1607) that the unprotected aziridine aldehyde 4, which exists as a mixture of dimers, condensed smoothly with the Ohira reagent 5 to give the alkynyl aziridine 6. David M. Hodgson of the University of Oxford successfully (Angew. Chem. Int. Ed. 2010, 49, 2900) deprotonated the azetidine thioamide 7 to give, after allylation, the azetidine 8. Varinder K. Aggarwal of the University of Bristol devised (Chem. Commun. 2010, 267) a Pd catalyst for the cyclocarbonylation of an alkenyl aziridine 9 to give the β-lactam 10. Iain Coldham of the University of Sheffield used (J. Org. Chem. 2010, 75, 4069) the ligand they had developed to effect enantioselective allylation of the pyrrolidine derivative 11. The corrresponding piperidine worked as well. John P. Wolfe of the University of Michigan established (Organic Lett. 2010, 12, 2322) that the Pd-mediated cyclization of 13 to 15 could be effected with high diastereocontrol. Christopher G. Frost of the University of Bath optimized (Angew. Chem. Int. Ed. 2010, 49, 1825) the tandem Ru-mediated conjugate addition/cyclization of 16 to give 18 in high ee. Barry M. Trost of Stanford University extended (J. Am. Chem. Soc. 2010, 132, 8238) their studies of trimethylenemethane cycloaddition to the ketimine 19, leading to the substituted pyrrolidine 21 in high ee. Pher G. Andersson of Uppsala University optimized (J. Am. Chem. Soc. 2010, 132, 8880) an Ir catalyst for the enantioselective hydrogenation of readily prepared tetrahydropyridines such as 22. Min Shi of the Shanghai Institute of Organic Chemistry devised (J. Org. Chem. 2010, 75, 3935) a Pd catalyst for enantioselective conjugate addition to the prochiral pyridone 24. Xiaojun Huang of Roche Palo Alto prepared (Tetrahedron Lett. 2010, 51, 1554) the monoacid 26 by enantioselective methanolysis of the anhydride. Selective formylation of the ester led to the pyridone 27.
APA, Harvard, Vancouver, ISO, and other styles
4

Taber, Douglass F. "C–N Ring Construction: The Waser Synthesis of Jerantinine E." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0053.

Full text
Abstract:
James A. Bull of Imperial College London prepared (J. Org. Chem. 2013, 78, 6632) the aziridine 2 with high diastereocontrol by adding the anion of diiodomethane to the imine 1. Karl Anker Jørgensen of Aarhus University observed (Chem. Commun. 2013, 49, 6382) high ee in the distal aziridination of 3 to give 4. Benito Alcaide of the Universidad Complutense de Madrid and Pedro Almendros of ICOQ- CSIC Madrid reduced (Adv. Synth. Catal. 2013, 355, 2089) the β-lactam 5 to the azetidine 6. Hiroaki Sasai of Osaka University added (Org. Lett. 2013, 15, 4142) the allenoate 8 to the imine 7, delivering the azetidine 9 in high ee. Tamio Hayashi of Kyoto University, the National University of Singapore, and A*STAR devised (J. Am. Chem. Soc. 2013, 135, 10990) a Pd catalyst for the enanti­oselective addition of the areneboronic acid 11 to the pyrroline 10 to give 12. Ryan A. Brawn of Pfizer (Org. Lett. 2013, 15, 3424) reported related results. Nicolai Cramer of the Ecole Polytechnique Fédérale de Lausanne developed (J. Am. Chem. Soc. 2013, 135, 11772) a Ni catalyst for the cyclization of the formamide 13 to the lactam 14. Andrew D. Smith of the University of St. Andrews used (Org. Lett. 2013, 15, 3472) an organocatalyst to cyclize 15 to 16. Jose L. Vicario of the Universidad del Pais Vasco effected (Synthesis 2013, 45, 2669) the multicomponent coupling of 17, 18, and 19, mediated by an organocatalyst, to construct 20 in high ee. André Beauchemin of the University of Ottawa explored (J. Org. Chem. 2013, 78, 12735) the thermal cyclization of ω-alkenyl hydroxyl amines such as 21. Abigail G. Doyle of Princeton University developed (Angew. Chem. Int. Ed. 2013, 52, 9153) a Ni catalyst for the enantioselective addition of aryl zinc bromides such as 24 to the pro­chiral 23, to give 25 in high ee. Dennis G. Hall of the University of Alberta developed (Angew. Chem. Int. Ed. 2013, 52, 8069) an in situ preparation of the allyl boronate 26 in high ee. Addition to the aldehyde 27 proceeded with high diasteroselectivity.
APA, Harvard, Vancouver, ISO, and other styles
5

Taber, Douglass F. "C–N Ring Construction: The Hattori Synthesis of (+)-Spectaline." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0056.

Full text
Abstract:
Magnus Rueping of RWTH Aachen University found (Chem. Commun. 2015, 51, 2111) that under Fe catalysis, a Grignard reagent would couple with the iodoazetidine 1 to give the substituted azetidine 2. Timothy F. Jamison of MIT established (Chem. Eur. J. 2015, 21, 7379) a protocol for converting 3, readily available from commercial homoserine lactone, to the alkylated azetidine 4. Long-Wu Ye of Xiamen University used (Chem. Commun. 2015, 51, 2126) a gold catalyst to cyclize 5, readily prepared in high ee, to the versatile ene sulfonamide 6. Chang- Hua Ding and Xue-Long Hou of the Shanghai Institute of Organic Chemistry added (Angew. Chem. Int. Ed. 2015, 54, 1604) the racemic aziridine 7 to the enone 8 to give the pyrrolidine 9 in high ee. Arumugam Sudalai of the National Chemical Laboratory employed (J. Org. Chem. 2015, 80, 2024) proline as an organocatalyst to mediate the addition of 11 to 10, leading to the pyrrolidine 12. Aaron D. Sadow of Iowa State University developed (J. Am. Chem. Soc. 2015, 137, 425) a Zr catalyst for the enantioselective cyclization of the prochiral 13 to 14. Masahiro Murakami of Kyoto University devised (Angew. Chem. Int. Ed. 2015, 54, 7418) a Rh catalyst for the enantioselective ring expansion of the photocycliza­tion product of 15 to the enamine 16. Sebastian Stecko and Bartlomiej Furman of the Polish Academy of Sciences reduced (J. Org. Chem. 2015, 80, 3621) the carbohydrate-derived lactam 17 with the Schwartz reagent to give an intermediate that could be coupled with an isonitrile, leading to the amide 18. Lei Liu of Shandong University oxidized (Angew. Chem. Int. Ed. 2015, 54, 6012) the alkene 19 in the presence of 20 to give 21. Tomislav Rovis of Colorado State University optimized (J. Am. Chem. Soc. 2015, 137, 4445) a Zn catalyst for the addition of 22 to the nitro alkene 23, leading, after reduction, to the piperidine 24. Carlos del Pozo and Santos Fustero of the Universidad de Valencia used (Org. Lett. 2015, 17, 960) a chiral auxiliary to direct the cyclization of 25 to the bicyclic amine 26. In another illustration of the use of microwave irradiation to activate amide bond rotation, G. Maayan of Technion showed (Org. Lett. 2015, 17, 2110) that 27 could be cyclized efficiently to the medium ring lactam 28.
APA, Harvard, Vancouver, ISO, and other styles
6

Taber, Douglass F. "Alkaloid Synthesis: Penaresidin A (Subba Reddy), Allokainic Acid (Saicic), Sedacryptine (Rutjes), Lepistine (Yokoshima/Fukuyama), Septicine (Hanessian), Lyconadin C (Dai)." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0058.

Full text
Abstract:
Penaresidin A 3, isolated from the Okinawan marine sponge Penares sp., is a potent activator of actomyosin ATPase. B. V. Subba Reddy of the Indian Institute of Chemical Technology prepared (Tetrahedron Lett. 2014, 55, 49) the azetidine ring of 3 by mesyl­ation of the hydroxy sulfonamide 2, derived from 1, followed by cyclization. Allokainic acid 6 has become a useful tool for neurological studies. Radomir N. Saicic of the University of Belgrade found (Org. Lett. 2014, 16, 34) that the Tsuji–Trost cyclization of 4 to 5 proceeded with high diastereoselectivity, presumably by way of the enamine of the aldehyde. Floris P. J. T. Rutjes of Radboud University Nijmegen prepared (Org. Lett. 2014, 16, 2038) the starting material 7 for (−)-sedacryptine 9 via an enantioselective Mannich addition. The reagent of choice for the Aza–Achmatowicz rearrangement of 7 to 8 proved to be mCPBA. The intriguing tricyclic alkaloid (−)-lepistine 12 was isolated from the mushroom Clitocybe fasciculate. En route to the first-ever synthesis of 12, Satoshi Yokoshima and Tohru Fukuyama of Nagoya University cyclized (Org. Lett. 2014, 16, 2862) the gly­cidol-derived sulfonamide 10 to the azacycle 11. (+)-Septicine 15 is the biogenetic precursor to the phenanthrene alkaloid (+)-tylophorine. Stephen Hanessian of the Université de Montréal prepared (Org. Lett. 2014, 16, 232) 15 by condensing the proline-derived ketone 13 with the aldehyde 14. Mingji Dai of Purdue University elaborated (Angew. Chem. Int. Ed. 2014, 53, 3922) the amine 16 to the enone 17 by intramolecular Mannich alkylation followed by methylenation and allylic oxidation. Condensation with the sulfoxide 18 then delivered lyconadin C 19.
APA, Harvard, Vancouver, ISO, and other styles
7

Taber, Douglass F. "C–N Ring Construction: The Weinreb Synthesis of Myrioneurinol." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0055.

Full text
Abstract:
Terminal epoxides such as 1 are readily available in high enantiomeric excess. Christopher D. Bray of Queen Mary University of London observed (Tetrahedron Lett. 2014, 55, 5890) clean inversion in the conversion of 1 to the aziridine 3 with the reagent 2. Yong-Chun Luo and Peng-Fei Xu of Lanzhou University opened (Org. Lett. 2014, 16, 4896) the activated cyclopropane 4 with benzyl azide, then heated the adduct to expel N2, leading to the azetidine 5. Zhenming Du of Roche Shanghai and Michelangelo Scalone of Roche Basel devel­oped (Org. Process Res. Dev. 2014, 18, 1702) practical conditions for the asymmetric hydrogenation of 6 to the pyrrolidine 7. Young Ho Rhee of the Pohang University of Science and Technology showed (Chem. Eur. J. 2014, 20, 16391) that depending on the diol protecting group, addition of allyl silane to 8 could lead to either the cis product 9 or the trans diastereomer (not illustrated). Ohyun Kwon of UCLA used (J. Am. Chem. Soc. 2014, 136, 11890) an organocatalyst to add the racemic allene 10 to 11 to give 12 in high ee. Tom Livinghouse of Montana State University cyclized (Angew. Chem. Int. Ed. 2014, 53, 14352) the hydrazine 13 into an intermediate organozinc species that was then coupled with allyl bromide to give 14. Yonggang Chen of Merck Process and Xumu Zhang of Rutgers University devised (Angew. Chem. Int. Ed. 2014, 53, 12761) practical conditions for the reduction of 15 to the piperidine 16. Teck-Peng Loh of the Nanyang Technological University and the University of Science and Technology of China effected (Chem. Commun. 2014, 50, 8324) asymmetric phenylation of biomass-derived 17 to give an intermediate that was oxidatively rearranged, then reduced to 18. Robert R. Knowles of Princeton University showed (J. Am. Chem. Soc. 2014, 136, 12217) that the cyclization of 19 to 20 proceeded with high diastereoselectivity. Maria J. Alves of the Universidade do Minho osmylated (Synlett 2014, 25, 1751) the adduct from the Diels–Alder cycload­dition of 22 to 21 to give 23 in high ee.
APA, Harvard, Vancouver, ISO, and other styles
8

Taber, Douglass F. "C–N Ring Construction: The Hoye Synthesis of (±)-Leuconolactam." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0057.

Full text
Abstract:
Manas K. Ghorai of the Indian Institute of Technology, Kanpur depended (J. Org. Chem. 2013, 78, 2311) on memory of chirality during deprotonation to convert 1 to the aziridine 3. X. Peter Zhang of the University of South Florida demonstrated (Angew. Chem. Int. Ed. 2013, 52, 5309) that Co-catalyzed enantioselective aziridination is compatible with fluoro-aromatics such as 5. David M. Hodgson of the University of Oxford prepared (J. Org. Chem. 2013, 78, 1098) the azetidine 8 by double deprotonation of 7 followed by acylation. Laurel L. Schafer of the University of British Columbia assembled (Org. Lett. 2013, 15, 2182) 11 by Ta-catalyzed aminoalkylation of 10 with 9, followed by cyclization. Nicholas A. Magnus of Eli Lilly reduced (J. Org. Chem. 2013, 78, 5768) the ketone 12 to the alcohol 13 with high de and ee. Pei-Qiang Huang of Xiamen University effected (J. Org. Chem. 2013, 78, 1790) the reductive addition of 14 to 15 to give 16. The titanocene protocol reported (Angew. Chem. Int. Ed. 2013, 52, 3494) by Xiao Zheng, also of Xiamen University, effectively mediated similar transformations. En route to (–)-quinocarcin, Nobutaka Fujii and Hiroaki Ohno of Kyoto University cyclized (Chem. Eur. J. 2013, 19, 8875) 17 to 18 with high diastereoselectivity. Dipolar cycloaddition, long a workhorse of pyrrolidine synthesis, has been improved by enantioselective organocatalysis. For instance, Liu-Zhu Gong of the University of Science and Technology of China combined (Org. Lett. 2013, 15, 2676) 19, 20, and 21 to give the triester 22. Qi-Lin Zhou of Nankai University reduced (Angew. Chem. Int. Ed. 2013, 52, 6072) the tetrahydropyridine 23 to 24 in high ee. Takaaki Sato and Noritaka Chida of Keio University cyclized (Chem. Eur. J. 2013, 19, 678) the intermediate from reduction of 25 to the piperidine 26. Yasumasa Hamada of Chiba University devised (Tetrahedron Lett. 2013, 54, 1562) the rearrangement of 27 to the piperidine 28. In a synthesis of (–)-hippodamine, Shigeo Katsumura of Kwansei Gakuin University used (Org. Lett. 2013, 15, 2758) the chiral auxiliary 29 to direct the combination of 30 with 31 to give 32.
APA, Harvard, Vancouver, ISO, and other styles
9

Taber, Douglass F. "The Carreira Synthesis of (±)-Gelsemoxonine." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0104.

Full text
Abstract:
The traditional Chinese pharmacopeia includes Gelsemium elegans benth, from which the alkaloid gelsemoxonine 3 was isolated. Erick M. Carreira of the Eidgenössische Technische Hochschule Zürich envisioned (J. Am. Chem. Soc. 2013, 135, 8500) that the unusual azetidine ring of 3 could be established by Brandi contraction of 1 to give 2. Following Brandi and Salaün (Eur. J. Org. Chem. 1999, 2725), the hemiketal 4 was carried onto the aldehyde 9. Condensation with nitromethane followed by dehydration gave the unsaturated nitrile oxide, which cyclized to 10. Epoxidation of 10 across the more open face gave an intermediate epoxide. Addition of 11 to the epoxide, promoted by InBr3, delivered 12 with good stereocontrol. CeCl3-mediated addition of 1-propynyl lithium completed the assembly of 1. A cyclopropanone could be seen as the addition product of carbon monoxide to an alkene. On exposure of 1 to acid, this formal addition was reversed, leading to the β-lactam 2. A computational study of this cleavage was recently reported (Eur. J. Org. Chem. 2011, 5608). Conceptually, one can imagine protonation activating the C–N bond for cleavage, leading to an intermediate such as 14, which then fragments to the acylium ion, leading to cyclization. It is unlikely that 14 would have any real lifetime. On warming with the Petasis reagent, the Boc-protected β-lactam was converted to the alkene 15. Hydroboration proceeded to give the alcohol 16 as a single diastereomer. Reduction followed by oxidation to 17 then set the stage for intramolecular aldol condensation to give 18. The last challenge was the diastereoselective assembly of the N-methoxyoxindole. To this end, oxidation and dehydration of 18 led to the bromo amide 20. As hoped, Heck reductive cyclization proceeded across the more open face of the alkene, leading to 21. Hydroxyl-directed hydrosilylation of the pendant alkyne to give the ethyl ketone then completed the synthesis of gelsemoxonine 3. Twice in this synthesis, advantage was taken of the preparation and reactivity of heteroatom-substituted alkenes. Dimethyl dioxirane, generated as a solution in acetone, was sufficiently water free that the epoxide derived from 10 could survive long enough to react in a bimolecular sense with the ketene silyl acetal 11.
APA, Harvard, Vancouver, ISO, and other styles
10

Singh, Girija S. "Advances in synthesis and chemistry of azetidines." In Advances in Heterocyclic Chemistry. Elsevier, 2020. http://dx.doi.org/10.1016/bs.aihch.2019.10.001.

Full text
APA, Harvard, Vancouver, ISO, and other styles

Conference papers on the topic "Azetidine synthesis"

1

Kaufman, Teodoro, and Marcela Amongero. "ORGANOCATALYTIC APPROACH TO THE SYNTHESIS OF OPTICALLY ACTIVE 1,2,3-TRISUBSTITUTED AZETIDINES." In The 13th International Electronic Conference on Synthetic Organic Chemistry. MDPI, 2009. http://dx.doi.org/10.3390/ecsoc-13-00211.

Full text
APA, Harvard, Vancouver, ISO, and other styles
2

Sankar, P. Siva, K. Divya, G. Dinneswara Reddy, V. Padmavathi, and Grigory V. Zyryanov. "Synthesis, characterization and antimicrobial activity of azetidinone and thiazolidinone derivatives." In PROCEEDINGS OF THE 3RD INTERNATIONAL CONFERENCE ON AUTOMOTIVE INNOVATION GREEN ENERGY VEHICLE: AIGEV 2018. Author(s), 2019. http://dx.doi.org/10.1063/1.5087379.

Full text
APA, Harvard, Vancouver, ISO, and other styles
3

Luna, Amparo, Pedro Almendros, and Benito Alcaide. "Diastereoselective direct aldol reaction and subsequent cyclization of 2-azetidinone-tethered azides for the preparation of a 4-hydroxypipecolic acid analogue." In The 13th International Electronic Conference on Synthetic Organic Chemistry. MDPI, 2009. http://dx.doi.org/10.3390/ecsoc-13-00174.

Full text
APA, Harvard, Vancouver, ISO, and other styles
4

Nikalje, Anna Pratima, Mangesh Ghodke, Shailee Tiwari, Julio Seijas Vázquez, and M. Pilar Vazquez-Tato. "Microwave-Assisted Facile Synthesis and anticonvulsant evaluation of Novel N-(3-chloro-2-oxo-4-substituted phenyl azetidin-1-yl)-2-(1, 3-dioxoisoindolin-2-yl) acetamides." In The 21st International Electronic Conference on Synthetic Organic Chemistry. MDPI, 2017. http://dx.doi.org/10.3390/ecsoc-21-04810.

Full text
APA, Harvard, Vancouver, ISO, and other styles
You might also be interested in the extended bibliographies on the topic 'Azetidine synthesis' for particular source types:
Journal articles Dissertations / Theses
We offer discounts on all premium plans for authors whose works are included in thematic literature selections. Contact us to get a unique promo code!

To the bibliography