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Journal articles on the topic '5-7-5 Tricyclic Ring Systems'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

He, Jing, and Marc L. Snapper. "New cycloaddition/fragmentation strategies for preparing 5-7-5 and 5-7-6 fused tricyclic ring systems." Tetrahedron 69, no. 36 (2013): 7831–39. http://dx.doi.org/10.1016/j.tet.2013.05.129.

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2

Ovaska, Timo V., Jayme L. Roark, Christina M. Shoemaker, and Jon Bordner. "A convenient route to fused 5-7-6 tricyclic ring systems." Tetrahedron Letters 39, no. 32 (1998): 5705–8. http://dx.doi.org/10.1016/s0040-4039(98)01198-8.

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3

He, Jing, and Marc L. Snapper. "ChemInform Abstract: New Cycloaddition/Fragmentation Strategies for Preparing 5-7-5 and 5-7-6 Fused Tricyclic Ring Systems." ChemInform 45, no. 2 (2013): no. http://dx.doi.org/10.1002/chin.201402029.

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4

OVASKA, T. V., J. L. ROARK, C. M. SHOEMAKER, and J. BORDNER. "ChemInform Abstract: A Convenient Route to Fused 5-7-6 Tricyclic Ring Systems." ChemInform 29, no. 44 (2010): no. http://dx.doi.org/10.1002/chin.199844105.

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5

Fang, Xianjie, and Xiaofeng Tong. "Palladium-catalyzed cyclization of 1,6-enyne with 2-bromoarylaldehyde: domino sequence to [5-7-6] tricyclic ring systems." Tetrahedron Letters 51, no. 2 (2010): 317–20. http://dx.doi.org/10.1016/j.tetlet.2009.11.006.

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6

Mátyus, Péter, Luca Szalay, Endre Kasztreiner, Gyula Jerkovich, and György Rabloczky. "Synthesis of new tricyclic ring systems containing the pyrimido[5, 4-b][1, 4]oxazine skeleton." Journal of Heterocyclic Chemistry 26, no. 3 (1989): 739–40. http://dx.doi.org/10.1002/jhet.5570260341.

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7

Gaber, Hatem M., Mark C. Bagley, Sherif M. Sherif, and Mohsen A. Sayed. "Novel Phenylazo Derivatives of Condensed and Uncondensed Thiophene. Synthesis, Characterization, and Antimicrobial Studies." Zeitschrift für Naturforschung B 66, no. 6 (2011): 585–96. http://dx.doi.org/10.1515/znb-2011-0606.

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In the search for new therapeutic agents against microbial infections, two novel series of monocyclic and tricyclic 5-(phenylazo)thiophene systems were synthesized based on 3-amino-2-thioxopyrimidinone and 2-cyanoacetamidothiophene derivatives 4 and 6. Functionalization of the pyrimidine ring in precursor 4 resulted in the formation of the target tricyclic condensed thiophenes 7, 12, and 13a, b, by the application of a variety of addition, substitution, and condensation reactions. On the other hand, derivatization of the versatile cyanoacetylated compound 6 led to a second series of monocyclic

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8

Toze, Flavien A. A., Maryana A. Nadirova, Dmitriy F. Mertsalov, Julya S. Sokolova, Pavel V. Dorovatovskii, and Victor N. Khrustalev. "IMDAV reaction between phenylmaleic anhydride and thienyl(furyl)allylamines: synthesis and molecular structure of (3aSR,4RS,4aRS,7aSR)-5-oxothieno- and (3aSR,4SR,4aRS,7aSR)-5-oxofuro[2,3-f]isoindole-4-carboxylic acids." Acta Crystallographica Section E Crystallographic Communications 74, no. 10 (2018): 1400–1404. http://dx.doi.org/10.1107/s2056989018012239.

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The title compounds C24H21NO3S, I, and C24H21NO4, II, are the products of the IMDAV reaction between phenylmaleic anhydride and thienyl(furyl)allylamines. Their molecular structures comprise fused tricyclic systems containing thiophene, cyclohexene and pyrrolidine rings (I) or furan, cyclohexene and pyrrolidine rings (II). The central cyclohexene and pyrrolidine rings in both compounds adopt slightly twisted boat and envelope conformations, respectively. The dihedral angles between the basal plane of the pyrrolidine ring and the thiophene (in I) or furan (in II) ring plane are 22.74 (16) and 2

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9

Shafawati, M. T. Soraya, Fuyuhiko Inagaki, Takamasa Kawamura, and Chisato Mukai. "Syntheses of 6-8-5 tricyclic ring systems by carbonylative [2+2+1] cycloaddition of bis(allene)s." Tetrahedron 69, no. 5 (2013): 1509–15. http://dx.doi.org/10.1016/j.tet.2012.12.014.

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10

Spanò, Virginia, Marilia Barreca, Vincenzo Cilibrasi, et al. "Evaluation of Fused Pyrrolothiazole Systems as Correctors of Mutant CFTR Protein." Molecules 26, no. 5 (2021): 1275. http://dx.doi.org/10.3390/molecules26051275.

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Cystic fibrosis (CF) is a genetic disease caused by mutations that impair the function of the CFTR chloride channel. The most frequent mutation, F508del, causes misfolding and premature degradation of CFTR protein. This defect can be overcome with pharmacological agents named “correctors”. So far, at least three different classes of correctors have been identified based on the additive/synergistic effects that are obtained when compounds of different classes are combined together. The development of class 2 correctors has lagged behind that of compounds belonging to the other classes. It was s

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11

Shafawati, M. T. Soraya, Fuyuhiko Inagaki, Takamasa Kawamura, and Chisato Mukai. "ChemInform Abstract: Synthesis of 6-8-5 Tricyclic Ring Systems by Carbonylative [2 + 2 + 1] Cycloaddition of Bis(allene)s." ChemInform 44, no. 27 (2013): no. http://dx.doi.org/10.1002/chin.201327031.

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12

Frey, Barbara, Adam P. Wells, Frances Roden, et al. "Total Synthesis of the Pentacyclic Diterpenoid Tropone Hainanolidol." Australian Journal of Chemistry 53, no. 10 (2000): 819. http://dx.doi.org/10.1071/ch00124.

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The total synthesis of the unusual diterpenoid tropone, hainanolidol (1), discovered in the bark of the yew species, Cephalotaxus hainanensis, has been completed in 26 steps from 3,5-dimethylanisole. The intramolecular cyclopropanation reaction of the aryl ring in (30) by means of the rhodium mandelate-catalysed reaction of the diazoacetyl function was used to assemble the 5/7 ring system of (31), at the same time elaborating a cycloheptatriene moiety that could be transformed subsequently to the tropone functionality in the target molecule. While removing the acetal protecting group from (31)

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13

Kotha, Sambasivarao, and Ambareen Fatma. "Construction of [5/7/5] Fused Tricyclic Sulfones via Ring‐Rearrangement Metathesis." ChemistrySelect 5, no. 6 (2020): 1929–31. http://dx.doi.org/10.1002/slct.201904381.

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14

Kondaskar, Atul, Shilpi Kondaskar, Raj Kumar, et al. "Novel, Broad Spectrum Anticancer Agents Containing the Tricyclic 5:7:5-Fused Diimidazodiazepine Ring System." ACS Medicinal Chemistry Letters 2, no. 3 (2010): 252–56. http://dx.doi.org/10.1021/ml100281b.

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15

Xu, Chen, Zheng Liu, Huifei Wang, et al. "Rapid Construction of [5−6−7] Tricyclic Ring Skeleton ofCalyciphyllineAlkaloid Daphnilongeranin B." Organic Letters 13, no. 7 (2011): 1812–15. http://dx.doi.org/10.1021/ol200312q.

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16

Govindan, E., PanneerSelvam Yuvaraj, Boreddy Siva Rami Reddy, K. Premalatha, and A. SubbiahPandi. "(4S)-5′-Chloro-3,7,7-trimethyl-5,6,7,8-tetrahydro-4H-spiro[1,2-oxazolo[5,4-b]quinoline-4,3′-indole]-2′,5-dione." Acta Crystallographica Section E Structure Reports Online 70, no. 2 (2014): o173. http://dx.doi.org/10.1107/s1600536814000191.

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In the title compound, C20H18ClN3O3, the five- and six-membered heterocycles fused through a spiro C atom are inclined to each other at an angle of 87.4 (1)°. In the tricyclic ring system, the cyclohexene ring adopts an envelope conformation with the spiro atom as the flap. In the crystal, two sets of N—H...O hydrogen bonds link the molecules into columns containing centrosymmetricR22(7) ring motifs and propagating along theb-axis direction.

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17

Zhou, Jun, You-Xing Zhao, Cheng-Sen Li, and Xiao-Dong Luo. "A New Tricyclic 6-7-5-Ring Diterpene from Pliocene Fossil Tsuga dumosa." HETEROCYCLES 63, no. 4 (2004): 861. http://dx.doi.org/10.3987/com-03-9981.

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18

Guajardo Touche, Elsa M., Elda Gómez Loprz, Alfredo P. Reyes, Humberto Sánchez, Friedrich Honecker, and Hans Achenbach. "Parryin, a diterpene with a tricyclic 6-7-5-ring system from Salvia parryi." Phytochemistry 45, no. 2 (1997): 387–90. http://dx.doi.org/10.1016/s0031-9422(96)00807-2.

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19

Bhargava, Gaurav, Beatriz Trillo, Marisel Araya, Fernando López, Luis Castedo, and José L. Mascareñas. "Palladium-catalyzed [3C + 2C + 2C] cycloaddition of enynylidenecyclopropanes: efficient construction of fused 5-7-5 tricyclic systems." Chem. Commun. 46, no. 2 (2010): 270–72. http://dx.doi.org/10.1039/b919258a.

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20

Zeidler, Joanna. "Modified Tricyclic Analogues of Acyclovir. A Direct Alkynylation in the Fused Ring." Collection of Czechoslovak Chemical Communications 69, no. 8 (2004): 1610–30. http://dx.doi.org/10.1135/cccc20041610.

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Two types of new 7-alkynylated tricyclic analogues (3,9-dihydro-5H-imidazo[1,2-a]purin-9-ones) of acyclovir differing by the presence of N-5 substituent, a temporary 2-(4-nitrophenyl)ethyl or a permanent 3-hydroxypropyl were obtained by a Sonogashira coupling. 7-Alk-1-ynyl-5-(3-acetoxypropyl) compounds (19a-19d, 21a-21c) were efficiently prepared from 7-iodo, 7-iodo-6-methyl precursors 12 and 11, respectively, and deprotected while the products with unsubstituted N-5 were unstable (e.g. 17). Iodide 12 was generally less reactive than 11 and underwent a preferable reduction (48%) to deiodinated

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21

Bailey, William F., and Justin D. Fair. "Intramolecular carbolithiation cascades as a route to a highly strained carbocyclic framework: competition between 5-exo-trig ring closure and proton transfer." Beilstein Journal of Organic Chemistry 9 (March 14, 2013): 537–43. http://dx.doi.org/10.3762/bjoc.9.59.

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The preparation of fairly strained carbocyclic ring systems by intramolecular 5-exo-trig ring closure has been well documented, and the absence of proton transfers that would compromise such cyclizations is a hallmark of this chemistry. In an effort to explore the limitations of this approach to more highly strained systems, the preparation of a stellane (tricyclo[3.3.0.03,7]octane) framework by an intramolecular carbolithiation cascade involving three coupled 5-exo-trig cyclizations of the vinyllithium derived from 2-bromo-4-vinyl-1,6-heptadiene by lithium–bromine exchange was investigated. T

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22

Attia, Mohamed I., Nasser R. El-Brollosy, Hazem A. Ghabbour, Suhana Arshad, and Hoong-Kun Fun. "5-Methoxy-1-[(5-methoxy-1H-indol-2-yl)methyl]-1H-indole." Acta Crystallographica Section E Structure Reports Online 68, no. 4 (2012): o971. http://dx.doi.org/10.1107/s1600536812009257.

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In the title compound, C19H18N2O2, the two indole ring systems are essentially planar [maximum deviation = 0.015 (2) Å in both indole ring systems] and make a dihedral angle of 72.17 (7)° with each other. In the crystal, the molecules are linked into a zigzag chain along theaaxisviaN—H...O hydrogen bonds.

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23

Hong, Bor-Cherng, Shang-Hung Chen, Ellappan Sampath Kumar, Gene-Hsiang Lee, and Kuan-Jiuh Lin. "Intramolecular [2+2] Photocycloaddition-Fragmentation: Facile Entry to a Novel Tricyclic 5-6-7 Ring System." Journal of the Chinese Chemical Society 50, no. 4 (2003): 917–26. http://dx.doi.org/10.1002/jccs.200300129.

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24

Oishi, Takeshi, Makoto Yoritate, Takaaki Sato, and Noritaka Chida. "Crystal structure of (−)-(5R,7R,8S,9R,10S)-8-methyl-7-[(5R)-3-methyl-2-oxooxolan-3-en-5-yl]-1-aza-6-oxatricyclo[8.3.0.05,9]tridecan-13-one monohydrate." Acta Crystallographica Section E Crystallographic Communications 74, no. 4 (2018): 555–58. http://dx.doi.org/10.1107/s2056989018004425.

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The title compound, C17H23NO4·H2O, is an epimer of the natural tetracyclic alkaloid isosaxorumamide which consists of a fused 5–7–5 tricyclic core and a dihydrofuranone substituent. The terminal dihydrofuran ring is essentially planar with a maximum deviation of 0.0273 (14) Å from the mean plane and oxolane, azepane and pyrrolidine rings in the tricyclic ring system adopt twist, twist-chair and envelope forms, respectively. In the crystal, the amide and water molecules are linked by O—H...O hydrogen bonds, forming a tape structure running along the b-axis direction. The tapes are further conne

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25

Jin, Shangde, and Jürgen Liebscher. "Novel Tandem Cyclisations at the Piperazinedione Ring via Cope Rearrangement." Zeitschrift für Naturforschung B 57, no. 4 (2002): 377–82. http://dx.doi.org/10.1515/znb-2002-0403.

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Novel rearrangements of 3-ylidene-piperazine-2,5-dione (1) were achieved affording Cope rearrangement products 3 and 4 under neutral conditions or tricyclic piperazine-2,5-diones 5, rac-6 and 7 by additional tandem cyclisation in formic acid. Cope rearrangement products 3 and 4 were transformed into new quaternary α-amino acids 9 and 11 by hydrogenation and hydrolysis.

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26

Gao, Lingzhi, Bin Cheng, Huijie Yue, Suyan Cao, Jiang-Li Wang, and Liang Xu. "A bioinspired approach for construction of the [7-5-6-5] all-carbon tetracyclic core of logeracemin A." Organic Chemistry Frontiers 6, no. 6 (2019): 813–16. http://dx.doi.org/10.1039/c9qo00062c.

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27

Zang, Yi, Grégory Genta-Jouve, Yingyu Zheng, et al. "Griseofamines A and B: Two Indole-Tetramic Acid Alkaloids with 6/5/6/5 and 6/5/7/5 Ring Systems from Penicillium griseofulvum." Organic Letters 20, no. 7 (2018): 2046–50. http://dx.doi.org/10.1021/acs.orglett.8b00584.

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28

WASSERMANN, H. H., J. D. COOK, and C. B. VU. "ChemInform Abstract: Intramolecular Alkylation of 3-Hydroxypyrrole-2-carboxylates. Formation of 5/5, 5/6, and 5/7 ring Systems Related to Pyrrolidine Alkaloids." ChemInform 23, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199211251.

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29

Cuny, Eckehard. "Stereoselective Synthesis of Spiroacetal Domain Derivatives of the Plant Glycoside Ranuncoside and of Okadaic Acid and Dinophysistoxins-1 and 2 From Marine Algae." Natural Product Communications 15, no. 11 (2020): 1934578X2097115. http://dx.doi.org/10.1177/1934578x20971150.

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Spiroacetals constitute the central structural core element of numerous natural products and are mostly represented as bicyclic or tricyclic domains. Typical natural products with tricyclic spiroacetals are (+)-ranuncoside 1, a glycoside isolated from plants of the Ranuncalaceae family, and the algal toxins (+)-okadaic acid 2 and the (+)-dinophysistoxins-1 and 2 (3 and 4). These substances possess a spiro furan-dioxane-pyran ring system 5 and a spiro furan-pyran-pyran scaffold 6, which are both essential for biological activity. Corresponding analogs with spiro furan-dioxane-cyclohexane framew

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30

Zhang, Dewu, Xiaoyu Tao, Jimei Liu, et al. "Periconiasin G, a new cytochalasan with unprecedented 7/6/5 tricyclic ring system from the endophytic fungus Periconia sp." Tetrahedron Letters 57, no. 7 (2016): 796–99. http://dx.doi.org/10.1016/j.tetlet.2016.01.030.

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31

Huang, Feng, Zhong-Ke Yao, Yi Wang, Yuanyuan Wang, Jialing Zhang, and Zhi-Xiang Yu. "Cover Picture: RhI-Catalyzed Two-Component [(5+2)+1] Cycloaddition Approach toward [5-8-5] Ring Systems (Chem. Asian J. 7/2010)." Chemistry - An Asian Journal 5, no. 7 (2010): 1501. http://dx.doi.org/10.1002/asia.201090020.

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32

Liu, Ju, Zhi-Qiang Cai, Yang Wang, Yu-Li Sang, and Li-Feng Xu. "3-(2,4-Dichlorophenyl)-5-(4-fluorophenyl)-2-phenyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (2012): o1923. http://dx.doi.org/10.1107/s1600536812023641.

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In the title compound, C25H13Cl2F4N3, there are four planar systems, viz. three benzene rings and a pyrazolo[1,5-a]pyrimidine system [r.m.s. deviation = 0.002 Å]. The dihedral angle between the dichlorophenyl ring and the unsubstituted phenyl ring is 69.95 (5)°, while that between the fluorophenyl ring and the unsubstituted phenyl ring is 7.97 (10)°. The crystal packing is dominated by van der Waals interactions. A Cl...Cl interaction of 3.475 (3) Å also occurs.

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33

Pinna, Gérard Aimè, Mario Sechi, Giuseppe Paglietti, and Maria Antonietta Pirisi. "Addition reactions of Acetylenic Esters to 6,7-Dihydrobenzo[B]Furan-4(5H)-One, 6,7-Dihydroindol-4(5H)-One, 5,6-Dihydrobenzo[B]Furan-7(6H)-One and 5,6-Dihydroindol-7(6H)-One Ketoximes. Formation of Reduced Furo[G]- and Pyrrolo[G]-Indoles." Journal of Chemical Research 2003, no. 3 (2003): 117–20. http://dx.doi.org/10.3184/030823403103173426.

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Thermal rearrangement of 6,7-dihydrobenzo[ b]furan-4(5 H)-one and 4,5,6,7-tetrahydroindol-4-one 4(7)- O-( E)-(1,2-dimethoxycarbonylvinyl)ketoximes gave 4,5-dihydrofuro[2,3 g]- and 4,5-dihydropyrrolo[2,3 g]- and [3,2- g] indoles, three novel tricyclic systems

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34

Di Santo, R., R. Costi, M. Artico, et al. "1,2,5-Benzothiadiazepine and Pyrrolo[2,1-d]-[1,2,5]Benzothiadiazepine Derivatives with Specific Anti-Human Immunodeficiency Virus Type 1 Activity." Antiviral Chemistry and Chemotherapy 9, no. 2 (1998): 127–37. http://dx.doi.org/10.1177/095632029800900204.

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We synthesized and tested as novel inhibitors of human immunodeficiency virus type 1 (HIV-1) bi- and tricyclic thiadiazine ring homologues of 7-chloro-2-ethyl-2 H-1,2,4-benzothiadiazin-3-(4 H)-one 1,1-dioxide, which is a compound endowed with anti-HIV-1 activity at low micromolar concentrations. Benzothiadiazepine derivatives were obtained by alkylation of 8-chloro-2,3-dihydro-3-methyl-1,2,5-benzothiadiazepin-4(5 H)-one 1,1-dioxide, which was obtained by intramolecular cyclization of 2-(2-amino-5-chloro-benzenesulphonamido) propanoic acid. Pyrrolobenzothiadiazepines were synthesized from N-sub

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35

Barbero, Margherita, and Cristina Prandi. "Pseudoguaianolides: Recent Advances in Synthesis and Applications." Natural Product Communications 13, no. 3 (2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300303.

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Pseudoguaianolides belong to the class of sesquiterpene lactones and are characterized by the lactone ring cis or trans-anellated (in 6,7- or 7,8- position) to fused seven- and five-membered rings; they differ from guaianolides for the position of the methyl group in 5. The unusual tricyclic fused core 5/7/5 was a challenge and inspired new synthetic methodologies to install substituents with proper stereochemistry. Despite their potential of application in different fields, their exploitation is so far very limited. Because of this, with this review we wanted to give perspectives in terms of

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36

Mondal, Sujit, Ram N. Yadav, and Subrata Ghosh. "Expedient asymmetric synthesis of a functionalized 5-7-6 fused tricyclic skeleton present in caribenol A through ring opening-ring closing metathesis of a norbornene derivative." Tetrahedron Letters 50, no. 37 (2009): 5277–79. http://dx.doi.org/10.1016/j.tetlet.2009.07.012.

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37

Vázquez, M. A., F. Muñoz, J. Donoso, and F. García Blanco. "Spectroscopic study of the Schiff bases of dodecylamine with pyridoxal 5′-phosphate and 5′-deoxypyridoxal. A model for the Schiff bases of pyridoxal 5′-phosphate in biological systems." Biochemical Journal 279, no. 3 (1991): 759–67. http://dx.doi.org/10.1042/bj2790759.

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We recorded the absorption spectra of the Schiff bases of pyridoxal 5′-phosphate (PLP) and 5′-deoxypyridoxal (DPL) with dodecylamine (DOD) at different pH values. By applying deconvolution techniques to the spectra and analysing their different components we found that the above-mentioned Schiff bases in aqueous solutions of pH 7 adopted a conformation in which the pyridine ring is embedded in a very hydrophobic medium from which water is virtually completely excluded. This conformation in the same as that adopted by PLP when it acts as coenzyme for some enzymes such as glycogen phosphorylase.

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38

Lynch, Daniel E., and Ian McClenaghan. "2-Amino-5-(4-methoxybenzyl)-4-methyl-1,3-thiazolium chloride." Acta Crystallographica Section E Structure Reports Online 57, no. 1 (2000): o24—o25. http://dx.doi.org/10.1107/s1600536800017876.

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The structure of the title compound, C12H15ClN2OS, (I), comprises a twisted thiazolium base that associates to a free Cl ionviaN—H...Cl hydrogen-bonding interactions. The dihedral angle between the two ring systems is 79.65 (7)°.

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39

Antczak, Kazimierz, John F. Kingston, Alex G. Fallis, and Alfred W. Hanson. "A general intramolecular Diels–Alder approach to tricyclic sesquiterpenes: stereoselective total syntheses of (±)-sinularene and (±)-5-epi-sinularene." Canadian Journal of Chemistry 65, no. 1 (1987): 114–23. http://dx.doi.org/10.1139/v87-019.

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Stereoselective total syntheses of (±)-sinularene and (±)-5-epi-sinularene are described. The sequence employs a "blocked" cyclopentadiene in which the cyclopropane unit also serves as a latent methyl group. Thus intramolecular [4 + 2] cycloaddition of the substituted methyl spiro[2.4]hepta-4,6-dien-1-yl-2-pentenoate 13c affords 5-benzyloxy-6-isopropyl-8-carbomethoxytetracyclo[5.4.01,7.02,4.02,9]undec-10-ene (14c), which after selective hydrogenolysis generates the tricyclo[4.4.01,6.02,8]decane (sinularene) ring system. Removal of the secondary hydroxyl function by elimination and hydrogenatio

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40

Hakberdiev, Shukhrat M., Samat A. Talipov, Davranbek N. Dalimov, and Bakhtiyar T. Ibragimov. "2,2′-Bis{8-[(benzylamino)methylidene]-1,6-dihydroxy-5-isopropyl-3-methylnaphthalen-7(8H)-one}." Acta Crystallographica Section E Structure Reports Online 69, no. 11 (2013): o1626—o1627. http://dx.doi.org/10.1107/s1600536813027281.

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The asymmetric unit of the title compound, C44H44N2O6, contains two independent molecules with similar conformations. The dihydronaphthalene ring systems are approximately planar [maximum deviations = 0.036 (2), 0.128 (2), 0.0.24 (2) and 0.075 (2) Å]. The dihedral angle between two dihydronaphthalene ring systems is 83.37 (4)° in one molecule and 88.99 (4)° in the other. The carbonyl O atom is linked with the adjacent hydroxy and imino groupsviaintramolecular O—H...O and N—H...O hydrogen bonds. In the crystal, molecules are linked through O—H...O hydrogen bonds into layers parallel to (001), a

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41

Raja, R., J. Govindaraj, M. Suresh, R. Raghunathan, and A. SubbiahPandi. "Crystal structure of ethyl 5′′-fluoro-2′′,3-dioxo-6′,7′,8′,8a'-tetrahydro-2′H,3H,5′H-dispiro[benzo[b]thiophene-2,1′-indolizine-3′,3′′-indoline]-2′-carboxylate." Acta Crystallographica Section E Crystallographic Communications 71, no. 3 (2015): o156—o157. http://dx.doi.org/10.1107/s2056989015002121.

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In the title compound, C25H23FN2O4S, the fused piperidine ring of the octahydroindolizine ring system adopts a chair conformation and the five-membered ring has a twisted conformation on the N—C(spiro) bond. The mean planes of the benzothiophene and indoline ring systems are inclined to the mean plane of the pyrrolidine ring by 83.1 (1) and 84.9 (1)°, respectively, and to each other by 29.37 (17)°. In the crystal, molecules are linkedviapairs of N—H...O hydrogen bonds, forming inversion dimers with anR22(8) ring motif. The dimers are linkedviaC—H...O hydrogen bonds, forming slabs lying paralle

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42

Acosta Quintero, Lina M., Isidro Burgos, Alirio Palma, Justo Cobo, and Christopher Glidewell. "Similar molecular constitutions but different conformations and different supramolecular assemblies in two related fused tetracyclic benzo[b]pyrimido[5,4-f]azepine derivatives." Acta Crystallographica Section C Structural Chemistry 72, no. 1 (2016): 52–56. http://dx.doi.org/10.1107/s2053229615023876.

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A simple and effective two-step approach to tricyclic pyrimidine-fused benzazepines has been adapted to give the tetracyclic analogues. In (RS)-8-chloro-6-methyl-1,2,6,7-tetrahydropyrimido[5′,4′:6,7]azepino[3,2,1-hi]indole, C15H14ClN3, (I), the five-membered ring adopts an envelope conformation, as does the reduced pyridine ring in (RS)-9-chloro-7-methyl-2,3,7,8-tetrahydro-1H-pyrimido[5′,4′:6,7]azepino[3,2,1-ij]quinoline, C16H16ClN3, (II). However, the seven-membered rings in (I) and (II) adopt very different conformations, with the result that the methyl substituent occupies a quasi-axial sit

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43

Hieu, Truong Hong, Le Tuan Anh, Anatoly T. Soldatenkov, Nadezhda M. Kolyadina, and Victor N. Khrustalev. "Dimethyl 2-[24-acetyl-28-oxo-8,11,14-trioxa-24,27-diazapentacyclo[19.5.1.122,26.02,7.015,20]octacosa-2,4,6,15(20),16,18-hexaen-27-yl]but-2-enedioate." Acta Crystallographica Section E Structure Reports Online 68, no. 8 (2012): o2431—o2432. http://dx.doi.org/10.1107/s1600536812030644.

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The title compound, C31H34N2O9, is a product of the Michael addition of the cyclic secondary amine subunit of the (bispidino)aza-14-crown-4 ether to dimethyl acetylenedicarboxylate. The molecule comprises a tricyclic system containing the aza-14-crown-3 ether macrocycle and two six-membered piperidinone rings. The aza-14-crown-3-ether ring adopts a bowl conformation with a dihedral angle between the planes of the fused benzene rings of 51.14 (5)°. The central piperidone ring has a boat conformation, whereas the terminal piperidone ring adopts a chair conformation. The dimethyl ethylenedicarbox

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44

Murali Krishna, U., and G. K. Trivedi. "Studies towards the synthesis of FCRR toxin: an expeditious entry into 7–5–6 ring systems via [5+2] oxidopyrylium-alkene cycloaddition." Tetrahedron Letters 45, no. 2 (2004): 257–59. http://dx.doi.org/10.1016/j.tetlet.2003.10.185.

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45

Shakya, S. R., and T. Durst. "Studies on novel carbacephem analogs: synthesis of 7-methoxy-homo-PS-5 and a 7-methoxy-8-epi-homothienamycin intermediate." Canadian Journal of Chemistry 70, no. 8 (1992): 2142–47. http://dx.doi.org/10.1139/v92-269.

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The synthesis of two carbacephems bearing a 7-methoxy group and either an additional ethyl (PS-5) or hydroxyethyl (thienamycin) side chain has been completed. Rhodium carbenoid insertion methodology was used to generate the bicyclic ring systems.

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46

GUAJARDO TOUCHE, E. M., E. GOMEZ LOPEZ, A. REYES P., H. SANCHEZ, F. HONECKER, and H. ACHENBACH. "ChemInform Abstract: Constituents of Tropical Medicinal Plants. Part 82. Parryin, a Diterpene with a Tricyclic 6-7-5-Ring System from Salvia parryi." ChemInform 28, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.199735227.

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47

Kreher, Richard P., та Gerald Dyker. "Struktur und Reaktivität von isoanellierten heterocyclischen Systemen mit Anπ- und (4n+2)π-Elektronen, XII [1]. 2-tert-Butyl-4-methyl-2,4-dihydropyrrolo[3,4-b]indole: Tricyclische Hetarene mit isoanellierten Pyrrolringen / Structure and Reactivity of Isoannelated Heterocyclic Systems with 4nπ- and (4n+2)π-Electrons, XII [1] 2-terr-Butyl-4-methyl-2,4-dihydropyrrolo[3,4-b]indoles: Tricyclic Hetarenes with Isoannelated Pyrrole Rings". Zeitschrift für Naturforschung B 42, № 4 (1987): 473–77. http://dx.doi.org/10.1515/znb-1987-0414.

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2-tert-Butyl-4-methyl-2,4-dihydropyrrolo[3,4-b]indole (4a) has been prepared via selective reduction of 2-rm-butyl-4-methyl-2,4-dihydropyrrolo[3,4-b]indol-l(2H)-one or -3(2H)-one 5 and 6 with diisobutylaluminiumhydride. The same precursors 5 and 6 can be transformed into 2-tert-butyl-4-methyl-2,4-dihydropyrrolo[3,4-b]indoles (4b) and (4c) bearing a methoxy group in 1- or 3-position via a two step procedure consisting in O-alkylation and CH-deprotonation. NMR Investigations afford an insight into the structure of the stable tricyclic hetarenes.

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48

Black, DS, N. Chaichit, BM Gatehouse, and GI Moss. "Unusual Formation of New Indole-Containing Heterocyclic Ring Systems." Australian Journal of Chemistry 40, no. 12 (1987): 1965. http://dx.doi.org/10.1071/ch9871965.

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The oxazinoindoletrione (3) underwent reaction with aqueous ammonia in methanol or ethanol to yield the polycyclic methyl or ethyl esters (4) and (5) respectively. Reaction of trione (3) with gaseous ammonia in dry ethanol gave the aminobenzodiazepinone (7). This compound lost ammonia on heating in toluene to give compound (11) and in the presence of methanol or ethanol gave the methyl or ethyl esters (9) and (10) respectively. The structures of compounds (4), (7) and (10) were all established by X-ray crystallography.

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49

Bunce, Richard, and Field Watts. "Synthesis of Aryl-Substituted 3,3a,4,5-Tetrahydropyrrolo[1,2-a] quinolin-1(2H)-ones and 2,3,4,4a,5,6-Hexahydro-1H-pyrido[1,2-a]quinolin-1-ones." Synthesis 51, no. 02 (2018): 564–72. http://dx.doi.org/10.1055/s-0037-1609940.

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A new route to the title benzo-fused angular tricyclic amides 3,3a,4,5-tetrahydropyrrolo- and 2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]quinolin-1-ones is reported from 1-(tert-butyl) 6-ethyl 3-oxohexanedioate and 1-(tert-butyl) 7-ethyl 3-oxoheptanedioate. Alkylation of these β-keto diesters with a series of 2-nitrobenzyl bromides followed by acid hydrolysis and decarboxylation gives ethyl 6-(2-nitrophenyl)-4-oxohexanoates and ethyl 7-(2-nitrophenyl)-5-oxoheptanoates, respectively. Reductive amination under hydrogenation conditions followed by ester hydrolysis and condensative ring closure afford

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50

Blanchfield, JT, DJ Brecknell, IM Brereton, MJ Garson, and DD Jones. "Caloundrin B and Funiculatin A: New Polypropionates From Siphonariid Limpets." Australian Journal of Chemistry 47, no. 12 (1994): 2255. http://dx.doi.org/10.1071/ch9942255.

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Two new polypropionates, caloundrin B (11), systematic name (1″R,2R,3″R,4R,5S,5″R,6S,-7″R,8″S,9″S,10″R)-2-(6′-ethyl-3′,5′-dimethyl-4′-oxopyran-2′-yl)-6-(5″-ethyl-7″-hydroxy-8″,9″,10″-trimethyl-2″,4″,6″-trioxatricyclo[3.3.1.13,7]dec-3″-yl)-5-hydroxy-4-methylheptan-3-one, and funiculatin A (12), systematic name (2ξ,1′S,4R,5′S,6′S)-2-(1′-ethyl-4′,6′,8′-trimethyl-2𔈀,9′-dioxabicyclo[3.3.1]nona-3′,7′-dien-3′-yl)-4,6-dimethylnon-6-en-3-one, have been isolated from Siphonaria zelandica and S. funiculata respectively. The structures of the new compounds were deduced by two-dimensional n.m.r. spectrosco

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