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Journal articles on the topic 'Azacycle'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 February 2022

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1

Lee, Eun, Tae Seop Kang, Beom Jun Joo, Jin Sung Tae, Kap Sok Li, and Cheol Keun Chung. "Azacycle synthesis via radical cyclization of β-aminoacrylates." Tetrahedron Letters 36, no. 3 (January 1995): 417–20. http://dx.doi.org/10.1016/0040-4039(94)02223-x.

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2

Kudryavtsev, Konstantin V., Polina M. Ivantcova, and Andrei V. Churakov. "(1SR,3RS,3aSR,6aRS)-Methyl 5-methyl-4,6-dioxo-3-[2-(trifluoromethyl)phenyl]octahydropyrrolo[3,4-c]pyrrole-1-carboxylate." Acta Crystallographica Section E Structure Reports Online 69, no. 2 (January 4, 2013): o161—o162. http://dx.doi.org/10.1107/s1600536812051471.

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In the title compound, C16H15F3N2O4, the relative stereochemistry of the four stereogenic C atoms has been determined. The carboxymethyl and 2-(trifluoromethyl)phenyl substituents of the pyrrolidine cycle have acismutual arrangement. The five-membered saturated azacycle adopts an envelope conformation with the N atom occupying the flap position. In the crystal, adjacent molecules are combined in centrosymmetric dimers by two weak N—H...O hydrogen bonds.

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3

Biswas, Tanmoy, Titas Biswas, and Shital K. Chattopadhyay. "Synthesis of chiral oxa- and azacycle-fused anthraquinone derivatives." Tetrahedron: Asymmetry 21, no. 2 (February 2010): 232–36. http://dx.doi.org/10.1016/j.tetasy.2010.02.001.

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4

Jara, Paul, Nicolás Yutronic, and Guillermo González. "13C CP-MAS NMR of Azacycle-Thiourea Inclusion Compounds." Supramolecular Chemistry 9, no. 3 (August 1, 1998): 163–68. http://dx.doi.org/10.1080/10610279808034982.

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5

LEE, E., T. S. KANG, B. J. JOO, J. S. TAE, K. S. LI, and C. K. CHUNG. "ChemInform Abstract: Azacycle Synthesis via Radical Cyclization of β-Aminoacrylates." ChemInform 26, no. 21 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199521062.

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6

Morokuma, Kenji, Shuntaro Tsukamoto, Kyosuke Mori, Kei Miyako, Ryuichi Sakai, Raku Irie, and Masato Oikawa. "Menthyl esterification allows chiral resolution for the synthesis of artificial glutamate analogs." Beilstein Journal of Organic Chemistry 17 (February 24, 2021): 540–50. http://dx.doi.org/10.3762/bjoc.17.48.

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Herein, we report the enantiospecific synthesis of two artificial glutamate analogs designed based on IKM-159, an antagonist selective to the AMPA-type ionotropic glutamate receptor. The synthesis features the chiral resolution of the carboxylic acid intermediate by the esterification with ʟ-menthol, followed by a configurational analysis by NMR, conformational calculation, and X-ray crystallography. A mice in vivo assay showed that (2R)-MC-27, with a six-membered oxacycle, is neuroactive, whereas the (2S)-counterpart is inactive. It was also found that TKM-38, with an eight-membered azacycle, is neuronally inactive, showing that the activity is controlled by the ring C.

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7

Kotha, Sambasivarao, and Ongolu Ravikumar. "Synthesis of fused azacycle via Overman rearrangement and ring-rearrangement metathesis as key steps." Tetrahedron Letters 57, no. 18 (May 2016): 1994–96. http://dx.doi.org/10.1016/j.tetlet.2016.03.087.

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8

Wang, Yinli, Raphaël Oriez, Satoru Kuwano, Yousuke Yamaoka, Kiyosei Takasu, and Ken-ichi Yamada. "Oxa- and Azacycle Formation via Migrative Cyclization of Sulfonylalkynol and Sulfonylalkynamide with N-Heterocyclic Carbene." Journal of Organic Chemistry 81, no. 6 (March 10, 2016): 2652–64. http://dx.doi.org/10.1021/acs.joc.6b00182.

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9

Ciufolini, Marco A., Cynthia W. Hermann, Kenton H. Whitmire, and Norman E. Byrne. "Chemoenzymatic preparation of trans-2,6-dialkylpiperidines and of other azacycle building blocks. Total synthesis of (+)-desoxoprosopinine." Journal of the American Chemical Society 111, no. 9 (April 1989): 3473–75. http://dx.doi.org/10.1021/ja00191a078.

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10

Li, Shouming, and Shosuke Yamamura. "Synthesis of the tetracyclic ABCE ring subunit I, bearing the 13-membered azacycle, of manzamine A." Tetrahedron 54, no. 30 (July 1998): 8691–710. http://dx.doi.org/10.1016/s0040-4020(98)00479-7.

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11

Yu, Xinzhang, Songjie Yu, Jian Xiao, Boshun Wan, and Xingwei Li. "Rhodium(III)-Catalyzed Azacycle-Directed Intermolecular Insertion of Arene C–H Bonds into α-Diazocarbonyl Compounds." Journal of Organic Chemistry 78, no. 11 (May 20, 2013): 5444–52. http://dx.doi.org/10.1021/jo400572h.

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12

Roberts, Charis Amber, Bohyun Park, Li-Ping Xu, Jose B. Roque, Charles S. Yeung, Djamaladdin G. Musaev, Richmond Sarpong, and Rebecca Lyn LaLonde. "Sequential Norrish–Yang Cyclization and C–C Cleavage/Cross-Coupling of a [4.1.0] Fused Saturated Azacycle." Journal of Organic Chemistry 86, no. 17 (August 17, 2021): 12436–42. http://dx.doi.org/10.1021/acs.joc.1c01466.

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13

Mizufune, Hideya. "Efficient Azacycle Formations Developed in Japanese Pharmaceutical Industries: Elegancy, Logistics, and Training (ELT) “Sandwich” for Process Chemists." Organic Process Research & Development 23, no. 4 (January 31, 2019): 419–42. http://dx.doi.org/10.1021/acs.oprd.8b00412.

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14

Mizufune, Hideya, Hiroaki Yamamoto, Minoru Nakamura, and Shokyo Miki. "A new efficient synthetic strategy for N-(dialkylamino)azacycle as a tetrasubstituted hydrazine derivative using sodium triacyloxyborohydride." Tetrahedron 64, no. 27 (June 2008): 6275–80. http://dx.doi.org/10.1016/j.tet.2008.04.114.

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15

LI, S., and S. YAMAMURA. "ChemInform Abstract: Synthesis of the Tetracyclic ABCE Ring Subunit I, Bearing the 13-Membered Azacycle, of Manzamine A." ChemInform 29, no. 44 (June 19, 2010): no. http://dx.doi.org/10.1002/chin.199844255.

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16

Yu, Xinzhang, Songjie Yu, Jian Xiao, Boshun Wan, and Xingwei Li. "ChemInform Abstract: Rhodium(III)-Catalyzed Azacycle-Directed Intermolecular Insertion of Arene C-H Bonds into α-Diazocarbonyl Compounds." ChemInform 44, no. 41 (September 19, 2013): no. http://dx.doi.org/10.1002/chin.201341134.

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17

Yang, Luqin, Shiping Yan, Genglin Wang, Honggen Wang, Ruji Wang, and Xinkan Yao. "Synthesis and crystal structure of a novel dinuclear complex of cobalt(II) with a new benzimidazole-containing azacycle ligand." Polyhedron 14, no. 15-16 (August 1995): 2037–40. http://dx.doi.org/10.1016/0277-5387(95)00039-u.

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18

Sun, Zunming, Shanshan Hu, Yan Huo, and Zhihong Wang. "Titanium tetrachloride-mediated synthesis of N-aryl-substituted azacycles from cyclic ethers." RSC Advances 7, no. 8 (2017): 4363–67. http://dx.doi.org/10.1039/c6ra27325d.

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19

Sun, Qingyan, Pengfei Yan, Wanying Niu, Wenyi Chu, Xu Yao, Guanghui An, and Guangming Li. "NIR luminescence of a series of benzoyltrifluoroacetone erbium complexes." RSC Advances 5, no. 81 (2015): 65856–61. http://dx.doi.org/10.1039/c5ra12954k.

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20

Li, Chengwen, Yilin Zhao, Jiaxin Zhou, Xue Wang, Jingli Hou, Yuguang Song, Wenjuan Liu, and Guifang Han. "Synthesis of difluoroalkylated 2-azaspiro[4.5]decane derivatives via copper-catalyzed difluoroalkylation/dearomatization of N-benzylacrylamides." Organic & Biomolecular Chemistry 18, no. 41 (2020): 8376–80. http://dx.doi.org/10.1039/d0ob01833c.

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A copper-catalyzed synthesis of difluoroalkylated spiro-azacycles from N-benzylacrylamides is presented. The reaction involves the β-difluoroalkylation of acrylamide, 5-exo cyclization, and dearomatization.

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21

Korbad, Balaji L., and Sang-Hyeup Lee. "Synthesis of N-aryl substituted, five- and six-membered azacycles using aluminum-amide complexes." Chem. Commun. 50, no. 64 (2014): 8985–88. http://dx.doi.org/10.1039/c4cc04111a.

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N-Aryl substituted, five- and six-membered azacycles, isoindoles and tetrahydroisoquinolines, were synthesized from the reaction of corresponding cyclic ethers (n = 1, 2) with dimethylaluminum-amide reagents.

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22

Bai, Dachang, Jintao Xia, Fangfang Song, Xueyan Li, Bingxian Liu, Lihong Liu, Guangfan Zheng, Xifa Yang, Jiaqiong Sun, and Xingwei Li. "Rhodium(iii)-catalyzed diverse [4 + 1] annulation of arenes with 1,3-enynes via sp3/sp2 C–H activation and 1,4-rhodium migration." Chemical Science 10, no. 14 (2019): 3987–93. http://dx.doi.org/10.1039/c9sc00545e.

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23

Dong, Yanping, Pengfei Yan, Xiaoyan Zou, and Guangming Li. "Azacyclo-auxiliary ligand-tuned SMMs of dibenzoylmethane Dy(iii) complexes." Inorganic Chemistry Frontiers 2, no. 9 (2015): 827–36. http://dx.doi.org/10.1039/c5qi00079c.

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24

Tran, Van Hieu, Minh Thanh La, Soosung Kang, and Hee-Kwon Kim. "Practical direct synthesis of N-aryl-substituted azacycles from N-alkyl protected arylamines using TiCl4 and DBU." Organic & Biomolecular Chemistry 18, no. 26 (2020): 5008–16. http://dx.doi.org/10.1039/d0ob00880j.

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Highly efficient direct transformations from N-alkyl protected arylamines such as N-methyl-, N-ethyl-, N-isopropyl, and N-tert-butyl arylamines into N-aryl substituted azacycles in the presence of TiCl₄ and DBU have been developed.

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25

Choi, Yoona, Heejun Kim, and Seung Bum Park. "A divergent synthetic pathway for pyrimidine-embedded medium-sized azacycles through an N-quaternizing strategy." Chemical Science 10, no. 2 (2019): 569–75. http://dx.doi.org/10.1039/c8sc04061c.

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A new divergent synthetic pathway for skeletally distinct pyrimidine-containing medium-sized azacycles was developed. Diversity-generating reactions via selective bond cleavages or migrations from N-quaternized intermediates were designed, and 14 discrete core skeletons were synthesized in an efficient manner. The skeletal diversity of the resulting molecular frameworks was confirmed by chemoinformatic analysis.

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26

Kim, Minjun, Jaebong Jang, Goyoung Choi, Sungkyun Chung, Changjin Lim, Joonseong Hur, Hyun Kim, et al. "Conversion of Medium-Sized Lactams to α-Vinyl or α-Acetylenyl Azacycles via N,O-Acetal TMS Ethers." Molecules 23, no. 11 (November 19, 2018): 3023. http://dx.doi.org/10.3390/molecules23113023.

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α-Vinyl or α-acetylenyl azacycles were easily synthesized from 7- to 9-membered lactams and 6- to 9-membered lactams via N,O-acetal trimethylsilyl (TMS) ethers. Organocopper and organostannane reagents afforded reasonable yields for the respective N-acyliminium ion vinylation and acetylenylation intermediates generated from N,O-acetal TMS ethers in the presence of a Lewis acid.

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27

Tabuchi, Hitoshi, Harumoto Kawaguchi, Hisashi Taniguchi, Hideyuki Imazaki, and Yoshio Hayase. "Anticoccidial Activity of Some Azacyclo Organoborinates." HETEROCYCLES 60, no. 1 (2003): 177. http://dx.doi.org/10.3987/com-02-9641.

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28

Yang, Qi-Liang, Ming-Sheng Xie, Chao Xia, Huan-Li Sun, Dan-Jie Zhang, Ke-Xin Huang, Zhen Guo, Gui-Rong Qu, and Hai-Ming Guo. "A rapid and divergent access to chiral azacyclic nucleoside analogues via highly enantioselective 1,3-dipolar cycloaddition of β-nucleobase substituted acrylates." Chem. Commun. 50, no. 94 (2014): 14809–12. http://dx.doi.org/10.1039/c4cc06632d.

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29

Kamijo, Shin, Kaori Kamijo, and Toshihiro Murafuji. "Aryl Ketone Mediated Photoinduced Radical Coupling for the Alkylation of Benzazoles Employing Saturated Heterocyclic Compounds." Synthesis 51, no. 20 (July 31, 2019): 3859–64. http://dx.doi.org/10.1055/s-0037-1611895.

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An aryl ketone mediated synthesis of 2-alkylated benzazoles was achieved via radical coupling under photoirradiation starting from saturated heterocycles and 2-sulfonylated benzazoles, such as benzothiazoles, benzoxazole, and benzimidazole. Heterocyclic compounds, including a cyclic ether, azacycles, and tetrahydrothiophene, were applicable, and the benzazole unit was site-selectively installed at the carbon center proximal to the heteroatom. The present transformation takes place at ambient temperature under neutral reaction conditions without the aid of any metallic catalysts or reagents.

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30

Matsuda, Yoshiro, and Hiromi Gotou. "The Chemistry of Antiaromatic Azacycl[3.3.3]azines." HETEROCYCLES 26, no. 10 (1987): 2757. http://dx.doi.org/10.3987/r-1987-10-2757.

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31

Yang, Wan-Wan, Jing-Wen Zhang, Lu-Lu Chen, Ji-Ya Fu, Jun-Yan Zhu, and Yan-Bo Wang. "Controllable synthesis of 3-iodo-2H-quinolizin-2-ones and 1,3-diiodo-2H-quinolizin-2-ones via electrophilic cyclization of azacyclic ynones." Chemical Communications 55, no. 84 (2019): 12607–10. http://dx.doi.org/10.1039/c9cc06250e.

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An efficient approach was developed to divergently synthesize 3-ipdo-2H-quinolizin-2-ones and 1,3-diiodo-2H-quinolizin-2-ones from azacyclic ynones with high regioselectivity under metal-free, room temperature conditions in air.

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32

Andrés, Patricia, Gema Ballano, M. Isabel Calaza, and Carlos Cativiela. "Synthesis of α-aminoboronic acids." Chemical Society Reviews 45, no. 8 (2016): 2291–307. http://dx.doi.org/10.1039/c5cs00886g.

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This review provides an overview of methodologies for the synthesis of acyclic, carbocyclic and azacyclic α-aminoboronic acid derivatives. Preparation routes towards these challenging compounds in either their racemic or their enantiomerically pure form are discussed.

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33

Kim, Ikyon, Anuradha Dagar, and Dirgha Raj Joshi. "Solvent-Controlled Divergent Syntheses of Polycyclic N-Fused Heteroaromatics." Synthesis 52, no. 19 (June 16, 2020): 2841–56. http://dx.doi.org/10.1055/s-0040-1707865.

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Due to a growing interest in aza-fused polyaromatic systems among various sciences, enormous attention has been continuously paid to design and synthesize novel chemotypes of N-fused heterocycles. During the course of continued efforts in this line, it was found that divergent access to new polycyclic N-fused heteroaromatics was enabled by choice of reaction solvent. Described herein are solvent-controlled selective approaches to three novel N-fused azacycles, benzo-[d]imidazole-pyrrolo[1,2-a]pyrazine hybrids, under mild conditions. The plausible reaction mechanism for each class of compound is suggested as well.

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34

Tabuchi, Hitoshi, Harumoto Kawaguchi, Hisashi Taniguchi, Hideyuki Imazaki, and Yoshio Hayase. "Synthesis and Anticoccidial Activity of Some Azacyclo Organoborinates." HETEROCYCLES 57, no. 7 (2002): 1319. http://dx.doi.org/10.3987/com-02-9496.

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35

Lynch, Stephen M., Laykea Tafesse, Kevin Carlin, Parijat Ghatak, Bin Shao, Haissam Abdelhamid, and Donald J. Kyle. "N-Aryl azacycles as novel sodium channel blockers." Bioorganic & Medicinal Chemistry Letters 25, no. 1 (January 2015): 48–52. http://dx.doi.org/10.1016/j.bmcl.2014.11.023.

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36

Chattopadhyay, Amit Kumar, and Stephen Hanessian. "Cyclic enaminones. Part II: applications as versatile intermediates in alkaloid synthesis." Chemical Communications 51, no. 92 (2015): 16450–67. http://dx.doi.org/10.1039/c5cc05892a.

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Among many other strategies, the enaminone approach is an important strategy to construct and diversify the azacyclic core in various alkaloids syntheses. In this brief review we discuss the application of cyclic enaminones as building blocks, as well as potential intermediates in the total synthesis of selected alkaloids.

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37

Takemoto, Yoshiji, Hideto Miyabe, Kazumasa Yoshida, Yusuke Kobayashi, and Akira Matsumura. "Synthesis of Azacycles Basedon Iridium-Catalyzed Sequential Allylic Amination." Synlett, no. 7 (2003): 1031–33. http://dx.doi.org/10.1055/s-2003-39317.

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38

Jeppesen, L., P. Sauerberg, P. H. Olesen, M. J. Sheardown, C. Thomsen, T. Rasmussen, A. Fink-Jensen, et al. "New potent muscarinic 1,2,5-thiadiazole-azacycles and dimers hereof." Life Sciences 64, no. 6-7 (January 1999): 555. http://dx.doi.org/10.1016/0024-3205(99)90466-6.

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39

Jeong, Jinseong, Sehoon Park, and Sukbok Chang. "Iridium-catalyzed selective 1,2-hydrosilylation of N-heterocycles." Chemical Science 7, no. 8 (2016): 5362–70. http://dx.doi.org/10.1039/c6sc01037g.

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A silylene-bridged Ir dimer in situ generated from [Ir(coe)₂Cl]₂ and Et₂SiH₂ was found to catalyze the hydrosilylation of N-heteroaromatics to furnish dearomatized azacyclic products with high activity (up to 1000 TONs), excellent selectivity, and good functional group tolerance.

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40

García, Isela, Manuel Pérez, Zoila Gándara, Generosa Gómez, and Yagamare Fall. "The furan approach to azacyclic compounds." Tetrahedron Letters 49, no. 22 (May 2008): 3609–12. http://dx.doi.org/10.1016/j.tetlet.2008.04.010.

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41

Norbeck, Daniel W., and James B. Kramer. "Synthesis of azacyclic 2-deoxy-KDO." Tetrahedron Letters 28, no. 7 (January 1987): 773–76. http://dx.doi.org/10.1016/s0040-4039(01)80986-2.

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42

Dombrovskii, V. A., and D. Yu Fonskii. "Synthesis of azacyclic prostaglandin analogs (review)." Pharmaceutical Chemistry Journal 27, no. 2 (February 1993): 121–31. http://dx.doi.org/10.1007/bf00781073.

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43

Li, Qian, An-Jun Deng, Li Li, Lian-Qiu Wu, Ming Ji, Hai-Jing Zhang, Zhi-Hong Li, et al. "Azacyclo-indoles and Phenolics from the Flowers of Juglans regia." Journal of Natural Products 80, no. 8 (July 24, 2017): 2189–98. http://dx.doi.org/10.1021/acs.jnatprod.6b00887.

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44

Wang, Qinxuan, and Jeremy A. May. "Synthesis of Bridged Azacycles and Propellanes via Nitrene/Alkyne Cascades." Organic Letters 22, no. 8 (April 3, 2020): 3039–44. http://dx.doi.org/10.1021/acs.orglett.0c00798.

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45

Verendel, J. Johan, Taigang Zhou, Jia-Qi Li, Alexander Paptchikhine, Oleg Lebedev, and Pher G. Andersson. "Highly Flexible Synthesis of Chiral Azacycles via Iridium-Catalyzed Hydrogenation." Journal of the American Chemical Society 132, no. 26 (July 7, 2010): 8880–81. http://dx.doi.org/10.1021/ja103901e.

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46

Chen, Lili, Yuhuan Yang, Luhua Liu, Qian Gao, and Senmiao Xu. "Iridium-Catalyzed Enantioselective α-C(sp3)–H Borylation of Azacycles." Journal of the American Chemical Society 142, no. 28 (June 29, 2020): 12062–68. http://dx.doi.org/10.1021/jacs.0c06756.

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47

Lertpibulpanya, Duanpen, Stephen P. Marsden, Ignacio Rodriguez-Garcia, and Colin A. Kilner. "Asymmetric Aza-Wittig Reactions: Enantioselective Synthesis of β-Quaternary Azacycles." Angewandte Chemie International Edition 45, no. 30 (July 24, 2006): 5000–5002. http://dx.doi.org/10.1002/anie.200601383.

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48

Lertpibulpanya, Duanpen, Stephen P. Marsden, Ignacio Rodriguez-Garcia, and Colin A. Kilner. "Asymmetric Aza-Wittig Reactions: Enantioselective Synthesis of β-Quaternary Azacycles." Angewandte Chemie 118, no. 30 (July 24, 2006): 5122–24. http://dx.doi.org/10.1002/ange.200601383.

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49

Mukai, Chisato, Minoru Kobayashi, Shoko Kubota, Yukie Takahashi, and Shinji Kitagaki. "Construction of Azacycles Based on Endo-Mode Cyclization of Allenes." Journal of Organic Chemistry 69, no. 6 (March 2004): 2128–36. http://dx.doi.org/10.1021/jo035729f.

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50

Miranda, Pedro O., Rubén M. Carballo, Víctor S. Martín, and Juan I. Padrón. "A New Catalytic Prins Cyclization Leading to Oxa- and Azacycles." Organic Letters 11, no. 2 (January 15, 2009): 357–60. http://dx.doi.org/10.1021/ol802593u.

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