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Journal articles on the topic 'Halocyclization'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 March 2023

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1

Moschona, Fotini, Christina Misirlaki, Nikolaos Karadimas, Maria Koutiva, Ioanna Savvopoulou, and Gerasimos Rassias. "Organocatalytic Asymmetric Halocyclization of Allylic Amides to Chiral Oxazolines Using DTBM-SEGPHOS—Mechanistic Implications from Hammett Plots." Symmetry 14, no. 5 (2022): 989. http://dx.doi.org/10.3390/sym14050989.

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The intramolecular halocyclization of alkenes possessing an internal heteroatom nucleophile leads to multifunctional heterocycles which are useful versatile intermediates in organic synthesis. The asymmetric chlorocyclisation of 2-substituted allylic amides gives access to chiral oxazolines bearing a chloromethyl moiety for further synthetic manipulation. The literature reports on this transformation involve complex syntheses of the 2-substituted allylic amides and cryogenic temperatures for achieving high enantioselectivities in the organocatalyzed halocyclization step. Based on the Heck reac

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2

de Andrade, Vitor, and Marcio de Mattos. "N-Halo Reagents: Modern Synthetic Approaches for Heterocyclic Synthesis." Synthesis 51, no. 09 (2019): 1841–70. http://dx.doi.org/10.1055/s-0037-1611746.

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Heterocyclic chemistry is an essential frontier in science and a source of novel biologically active compounds. The development of innovative synthetic methodologies that allows access to different heterocyclic rings is of critical interest to the scientific community. This review will focus on recent applications of N-halo compounds (e.g., N-halosuccinimides, trihaloisocyanuric acids, N-halosulfonamides, etc.) in heterocyclic construction via electrophilic cyclization, asymmetric halocyclization, oxidative cyclization, and radical processes.1 Introduction2 N-Halo Reagent Mediated Heterocyclic

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3

Kim, D. G. "Halocyclization of 2-allylthiobenzothiazole." Chemistry of Heterocyclic Compounds 34, no. 4 (1998): 505. http://dx.doi.org/10.1007/bf02290898.

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4

Kim, D. G. "Halocyclization of 2-allylthiopyridine." Chemistry of Heterocyclic Compounds 35, no. 3 (1999): 290–92. http://dx.doi.org/10.1007/bf02259357.

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5

Kim, D. G. "Halocyclization of 8-allylthioquinoline." Chemistry of Heterocyclic Compounds 33, no. 8 (1997): 989–91. http://dx.doi.org/10.1007/bf02253176.

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6

Subba Reddy, B. V., R. Anji Babu, B. Jagan Mohan Reddy, et al. "A short and highly convergent approach for the synthesis of rutaecarpine derivatives." RSC Advances 5, no. 35 (2015): 27476–80. http://dx.doi.org/10.1039/c4ra14093a.

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7

Xu, Jun, and Rongbiao Tong. "An environmentally friendly protocol for oxidative halocyclization of tryptamine and tryptophol derivatives." Green Chemistry 19, no. 13 (2017): 2952–56. http://dx.doi.org/10.1039/c7gc01341h.

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8

Zhang, Zhi-Qiang, and Feng Liu. "CuX2-mediated oxybromination/aminochlorination of unsaturated amides: synthesis of iminolactones and lactams." Organic & Biomolecular Chemistry 13, no. 24 (2015): 6690–93. http://dx.doi.org/10.1039/c5ob00520e.

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9

Yan, Jiahang, Zhiqiang Zhou, Qiaoqiao He, Guzhou Chen, Hongbo Wei, and Weiqing Xie. "The applications of catalytic asymmetric halocyclization in natural product synthesis." Organic Chemistry Frontiers 9, no. 2 (2022): 499–516. http://dx.doi.org/10.1039/d1qo01395e.

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Catalytic asymmetric halocyclization of olefinic substrate has evolved rapidly and been well utilized as a practical strategy for constructing enantioenriched cyclic skeletons in natural product synthesis.

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10

Fujioka, Hiromichi, and Kenichi Murai. "Recent Progress in Organocatalytic Asymmetric Halocyclization." HETEROCYCLES 87, no. 4 (2013): 763. http://dx.doi.org/10.3987/rev-12-762.

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11

Ishihara, K., A. Sakakura, and A. Ukai. "Halocyclization by a ‘Chiral Iodine Atom’." Synfacts 2007, no. 5 (2007): 0537. http://dx.doi.org/10.1055/s-2007-968404.

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12

Steinmann, Jens G., John H. Phillips, William J. Sanders, and Laura L. Kiessling. "Synthesis of Cyclic Sulfates by Halocyclization." Organic Letters 3, no. 22 (2001): 3557–59. http://dx.doi.org/10.1021/ol016674b.

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13

Kim, D. G. "Synthesis and halocyclization of 2-alkenylthioquinolines." Chemistry of Heterocyclic Compounds 44, no. 11 (2008): 1355–58. http://dx.doi.org/10.1007/s10593-009-0195-9.

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14

Sanz, R., V. Guilarte, E. Hernando, and A. Sanjuán. "Directedortho-Metalation-Halocyclization Route to Benzothiophenes." Synfacts 2011, no. 02 (2011): 0143. http://dx.doi.org/10.1055/s-0030-1259377.

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15

KIM, D. G., and E. R. ZAKIROVA. "ChemInform Abstract: Halocyclization of 8-Allyloxyquinolines." ChemInform 25, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199438200.

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16

KIM, D. G. "ChemInform Abstract: Halocyclization of 2-Allylthiobenzothiazole." ChemInform 29, no. 41 (2010): no. http://dx.doi.org/10.1002/chin.199841126.

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17

Kim, D. G. "ChemInform Abstract: Halocyclization of 2-Allylthiopyridine." ChemInform 31, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.200007127.

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18

KIM, D. G. "ChemInform Abstract: Halocyclization of 8-Allylthioquinoline." ChemInform 29, no. 10 (2010): no. http://dx.doi.org/10.1002/chin.199810055.

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19

Sun, Yuan-Ming, Liu-Zhu Yu, Zi-Zhong Zhu, Xu-Bo Hu, Yu-Ning Gao, and Min Shi. "Electronic halocyclization and radical haloazidation of benzene-linked 1,7-dienes for the synthesis of functionalized 3,1-benzoxazines." Organic & Biomolecular Chemistry 15, no. 3 (2017): 634–39. http://dx.doi.org/10.1039/c6ob02566h.

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Electronic halocyclization and radical haloazidation of benzene-linked 1,7-dienes by using TMSN<sub>3</sub> as an azidyl source and NBS as a halogen source has been disclosed in this paper, producing a series of functionalized 3,1-benzoxazines in moderate to good yields.

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20

Grossman, Robert B., and Robert J. Trupp. "The first reagent-controlled asymmetric halolactonizations. Dihydroquinidine-halogen complexes as chiral sources of positive halogen ion." Canadian Journal of Chemistry 76, no. 9 (1998): 1233–37. http://dx.doi.org/10.1139/v98-153.

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The first reagent-controlled asymmetric halolactonizations are described. Complexes of I+ with O-acyl- and O-aryldihydroquinidines are used to promote the asymmetric halolactonization of prochiral θ, δ-unsaturated carboxylic acids with low but measurable and reproducible enantioselectivity. Experimental factors affecting the ee's are described. Key words: halocyclization, halogenation, halonium ions, chiral, stereoselective.

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21

Kloeckner, Ulrich, Peter Finkbeiner, and Boris J. Nachtsheim. "Iodide-Catalyzed Halocyclization/Cycloaddition/Elimination Cascade Reaction." Journal of Organic Chemistry 78, no. 6 (2013): 2751–56. http://dx.doi.org/10.1021/jo302676g.

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22

Hamashima, Yoshitaka, and Yuji Kawato. "Enantioselective Bromocyclization of Allylic Amides Mediated by Phosphorus Catalysis." Synlett 29, no. 10 (2018): 1257–71. http://dx.doi.org/10.1055/s-0036-1591579.

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Halocyclization of alkenes is commonly employed to increase molecular complexity during organic synthesis because it enables double installation of heteroatoms on a carbon–carbon double bond. Moreover, stereodefined halogenated compounds are widely found among naturally occurring compounds and can serve as versatile chiral building blocks. Therefore, the development of asymmetric halocyclization reactions is of great interest and, in recent years, there has been remarkable progress in catalytic asymmetric halogenation reactions. This account summarizes recent progress made by our group on phos

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23

Maas, Gerhard, Vito A. Fiore, Michael Keim, and Roland Werz. "Electrophilic ipso-Halocyclization of N-Phenyl-N-triflylpropiolamides Leading to 8-Halo-1-azaspiro[4.5]deca-3,6,9-trien-2-ones." Synthesis 52, no. 10 (2020): 1489–97. http://dx.doi.org/10.1055/s-0039-1691733.

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N-Phenyl-N-triflylpropiolamides react with iodine chloride or iodine bromide by an intramolecular electrophilic ipso-halocyclization/nucleophilic halide addition sequence to furnish cyclohexadiene-spiro-γ-lactams. These products can undergo cleavage of the amide bond with primary amines and of the N–Cspiro bond with secondary amines, leading to N-alkyl-2-iodo-3-phenylacrylamides and N-(4-halophenyl)-2-iodo-3-(2-triflylamino)phenylacrylamides, respectively.

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24

Liu, Gong-Qing, and Yue-Ming Li. "Regioselective (Diacetoxyiodo)benzene-Promoted Halocyclization of Unfunctionalized Olefins." Journal of Organic Chemistry 79, no. 21 (2014): 10094–109. http://dx.doi.org/10.1021/jo501739j.

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25

Hennecke, Ulrich, and Michael Wilking. "Desymmetrization as a Strategy in Asymmetric Halocyclization Reactions." Synlett 25, no. 12 (2014): 1633–37. http://dx.doi.org/10.1055/s-0033-1341160.

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26

Sakakura, Akira, Atsushi Ukai, and Kazuaki Ishihara. "Enantioselective halocyclization of polyprenoids induced by nucleophilic phosphoramidites." Nature 445, no. 7130 (2007): 900–903. http://dx.doi.org/10.1038/nature05553.

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27

Xiao-Feng, Ren, and Edward Turos. "Regiochemical studies on halocyclization reactions of unsaturated sulfides." Tetrahedron Letters 34, no. 10 (1993): 1575–78. http://dx.doi.org/10.1016/0040-4039(93)85010-t.

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28

Kitagawa, Osamu, Tokushi Hanano, Kiyoshi Tanabe, Motoo Shiro, and Takeo Taguchi. "Enantioselective halocyclization reaction using a chiral titanium complex." Journal of the Chemical Society, Chemical Communications, no. 14 (1992): 1005. http://dx.doi.org/10.1039/c39920001005.

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29

Slivka, N. Yu, Yu I. Gevaza, and V. I. Staninets. "Halocyclization of Substituted 2-(Alkenylthio)pyrimidin-6-ones." Chemistry of Heterocyclic Compounds 40, no. 5 (2004): 660–66. http://dx.doi.org/10.1023/b:cohc.0000037323.22839.9f.

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30

Zheng, Tianyu, Xinyan Wang, Wing-Hin Ng, Ying-Lung Steve Tse, and Ying-Yeung Yeung. "Catalytic enantio- and diastereoselective domino halocyclization and spiroketalization." Nature Catalysis 3, no. 12 (2020): 993–1001. http://dx.doi.org/10.1038/s41929-020-00530-9.

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31

Murai, Kenichi, and Hiromichi Fujioka. "ChemInform Abstract: Recent Progress in Organocatalytic Asymmetric Halocyclization." ChemInform 44, no. 24 (2013): no. http://dx.doi.org/10.1002/chin.201324211.

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32

Liu, Kun, Yuqi Deng, Wenxu Song, Chunlan Song, and Aiwen Lei. "Electrochemical Dearomative Halocyclization of Tryptamine and Tryptophol Derivatives." Chinese Journal of Chemistry 38, no. 10 (2020): 1070–74. http://dx.doi.org/10.1002/cjoc.202000194.

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33

Steinmann, Jens G., John H. Phillips, William J. Sanders, and Laura L. Kiessling. "ChemInform Abstract: Synthesis of Cyclic Sulfates by Halocyclization." ChemInform 33, no. 10 (2010): no. http://dx.doi.org/10.1002/chin.200210046.

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34

Slivka, Mikhailo, Nataliya Korol, Valerij Pantyo, Vjacheslav Baumer та Vasil Lendel. "Regio- and stereoselective synthesis of [1,3]thiazolo[3,2-b][1,2,4]triazol-7-ium salts via electrophilic heterocyclization of 3-S-propargylthio-4Н-1,2,4-triazoles and their antimicrobial activity". Heterocyclic Communications 23, № 2 (2017): 109–13. http://dx.doi.org/10.1515/hc-2016-0233.

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AbstractA procedure for the preparation of the title salts via regioselective halocyclization of 3-S-propargylthio-4Н-1,2,4-triazoles is reported. Stereoselectivity of electrophilic heterocyclization depends on the nature of the electrophilic reagent: bromination is better than iodobromination and iodination. The heterocyclization with tellurium tetrahalogenides leads to the formation of a mixture of geometric isomers of the salts. Their structure was confirmed by 1H NMR, 13C NMR, НМВС and single crystal X-ray diffraction analysis.

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35

Höfler, Georg T., Andrada But, Sabry H. H. Younes, et al. "Chemoenzymatic Halocyclization of 4-Pentenoic Acid at Preparative Scale." ACS Sustainable Chemistry & Engineering 8, no. 7 (2020): 2602–7. http://dx.doi.org/10.1021/acssuschemeng.9b07494.

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36

Peuchmaur, Marine, Vincent Lisowski, Céline Gandreuil, Ludovic T. Maillard, Jean Martinez, and Jean-François Hernandez. "Solid-Phase Synthesis of Isocoumarins: A Traceless Halocyclization Approach." Journal of Organic Chemistry 74, no. 11 (2009): 4158–65. http://dx.doi.org/10.1021/jo900281a.

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37

Kalita, Elena V., Dmitry G. Kim, Oleg S. Eltsov, Taisiya S. Shtukina, and Irina V. Mukhametgaleeva. "Synthesis and halocyclization of 2-mercaptonicotinic acid propargyl derivatives." Chemistry of Heterocyclic Compounds 55, no. 4-5 (2019): 473–77. http://dx.doi.org/10.1007/s10593-019-02483-9.

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38

Rai, Vishakha, Ganesh Shivayogappa Sorabad, and Mahagundappa Rachappa Maddani. "CuX 2 Mediated Facile Halocyclization of N ‐Allyl Thioureas." ChemistrySelect 5, no. 22 (2020): 6565–69. http://dx.doi.org/10.1002/slct.202000593.

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39

Kloeckner, Ulrich, Peter Finkbeiner, and Boris J. Nachtsheim. "ChemInform Abstract: Iodide-Catalyzed Halocyclization/Cycloaddition/Elimination Cascade Reaction." ChemInform 44, no. 29 (2013): no. http://dx.doi.org/10.1002/chin.201329091.

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40

Liu, Na, Hao-Yuan Wang, Wei Zhang, et al. "Stereoselective Halocyclization of Alkenes With N -Acyl Hemiaminal Nucleophiles." Chirality 25, no. 11 (2013): 805–9. http://dx.doi.org/10.1002/chir.22219.

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41

Kalita, E. V., D. G. Kim, O. S. Yeltsov, and T. S. Shtukina. "Alkenyl derivatives of 5-nitro-2-pyridone: Synthesis and halocyclization." Russian Journal of Organic Chemistry 52, no. 8 (2016): 1148–53. http://dx.doi.org/10.1134/s1070428016080091.

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42

Kim, D. G., E. A. Vershinina, and V. V. Sharutin. "Halocyclization of 1-Allyl-6(7)-methylquinolin-2(1H)-ones." Russian Journal of Organic Chemistry 54, no. 4 (2018): 601–5. http://dx.doi.org/10.1134/s1070428018040140.

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43

Kim, D. G., K. Yu Petrova, T. V. Frolova, et al. "Halocyclization of 3-Allyl-5-ethyl-6-methyl-2-thiouracil." Russian Journal of Organic Chemistry 55, no. 9 (2019): 1333–37. http://dx.doi.org/10.1134/s1070428019090112.

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44

Ren, Xiao-Feng, Edward Turos, Charles H. Lake, and Melvyn Rowen Churchill. "Regiochemical and stereochemical studies on halocyclization reactions of unsaturated sulfides." Journal of Organic Chemistry 60, no. 20 (1995): 6468–83. http://dx.doi.org/10.1021/jo00125a038.

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45

Kim, D. G., and A. V. Zhuravlyova. "Halocyclization of 3-allylthio-5H-[1,2,4]triazino[5,6-b]indole." Chemistry of Heterocyclic Compounds 46, no. 7 (2010): 896–98. http://dx.doi.org/10.1007/s10593-010-0599-6.

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46

Younes, Sabry H. H., Florian Tieves, Dongming Lan та ін. "Chemoenzymatic Halocyclization of γ,δ‐Unsaturated Carboxylic Acids and Alcohols". ChemSusChem 13, № 1 (2019): 97–101. http://dx.doi.org/10.1002/cssc.201902240.

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47

Younes, Sabry H. H., Florian Tieves, Dongming Lan та ін. "Chemoenzymatic Halocyclization of γ,δ‐Unsaturated Carboxylic Acids and Alcohols". ChemSusChem 13, № 1 (2019): 5. http://dx.doi.org/10.1002/cssc.201903372.

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48

KITAGAWA, O., T. HANANO, K. TANABE, M. SHIRO, and T. TAGUCHI. "ChemInform Abstract: Enantioselective Halocyclization Reaction Using a Chiral Titanium Complex." ChemInform 23, no. 44 (2010): no. http://dx.doi.org/10.1002/chin.199244176.

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49

Chen, Guofei, and Shengming Ma. "Enantioselective Halocyclization Reactions for the Synthesis of Chiral Cyclic Compounds." Angewandte Chemie International Edition 49, no. 45 (2010): 8306–8. http://dx.doi.org/10.1002/anie.201003114.

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50

REN, X. F., and E. TUROS. "ChemInform Abstract: Regiochemical Studies on Halocyclization Reactions of Unsaturated Sulfides." ChemInform 24, no. 29 (2010): no. http://dx.doi.org/10.1002/chin.199329075.

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