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Journal articles on the topic 'Heterocyclic compounds Heterocyclic compounds Ring formation (Chemistry) Nitriles'

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Published: 4 June 2021

Last updated: 16 February 2022

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1

Hanusek, Jiří, and Vladimír Macháček. "Intramolecular base-catalyzed reactions involving interaction between benzene nitro groups and ortho carbon chains." Collection of Czechoslovak Chemical Communications 74, no. 5 (2009): 811–33. http://dx.doi.org/10.1135/cccc2008216.

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The review is focused on the understanding of processes involving chemical interaction between benzene nitro group and ortho carbon chain containing heteroatom (N, O, S) adjacent to the ring. In most cases these compounds undergo base-catalyzed cyclization to give heteroaromatic N-oxides that can be subsequently transformed to related heterocycles under the same conditions. However, in some cases, depending on substitution of the benzene ring, side chain or the base used, the formation of other compounds – both heterocyclic and non-heterocyclic such as nitroso and azoxy compounds, spiro Meisen

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2

Hemalatha, Kanagarajan, Gunabalan Madhumitha, Amir Kajbafvala, Narayanan Anupama, Rajesh Sompalle, and Selvaraj Mohana Roopan. "Function of Nanocatalyst in Chemistry of Organic Compounds Revolution: An Overview." Journal of Nanomaterials 2013 (2013): 1–23. http://dx.doi.org/10.1155/2013/341015.

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Heterocyclic motif is an important scaffold which has both industrial and pharmaceutical applications. These motifs can be prepared using wide variety of reaction conditions such as the use of expensive catalyst, toxic solvent, harsh reaction condition like the use of base, high temperature, and multistep reaction. Although various methods are involved, the chemistry arena is now shifted towards the greener way of synthesis. Nanocatalyst constitutes an important role in the green synthesis. This is because the activity of the catalyst resides in the exposed portion of the particles. By decreas

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3

Guan, Zong, Jan C. Namyslo, Martin H. H. Drafz, Martin Nieger, and Andreas Schmidt. "Dimerisation, rhodium complex formation and rearrangements of N-heterocyclic carbenes of indazoles." Beilstein Journal of Organic Chemistry 10 (April 10, 2014): 832–40. http://dx.doi.org/10.3762/bjoc.10.79.

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Deprotonation of indazolium salts at low temperatures gives N-heterocyclic carbenes of indazoles (indazol-3-ylidenes) which can be trapped as rhodium complexes (X-ray analysis). In the absence of Rh, the indazol-3-ylidenes spontaneously dimerize under ring cleavage of one of the N,N-bonds and ring closure to an indazole–indole spiro compound which possesses an exocyclic imine group. The E/Z isomers of the imines can be separated by column chromatography when methanol is used as eluent. We present results of a single crystal X-ray analysis of one of the E-isomers, which equilibrate in solution

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4

Francke, Robert. "Recent advances in the electrochemical construction of heterocycles." Beilstein Journal of Organic Chemistry 10 (December 3, 2014): 2858–73. http://dx.doi.org/10.3762/bjoc.10.303.

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Due to the fact that the major portion of pharmaceuticals and agrochemicals contains heterocyclic units and since the overall number of commercially used heterocyclic compounds is steadily growing, heterocyclic chemistry remains in the focus of the synthetic community. Enormous efforts have been made in the last decades in order to render the production of such compounds more selective and efficient. However, most of the conventional methods for the construction of heterocyclic cores still involve the use of strong acids or bases, the operation at elevated temperatures and/or the use of expens

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5

Bhattacharyya, Aditya. "Synthetic Routes to 1,4,5,6-Tetrahydropyrimidines: An Overview and Recent Advances." Current Organic Chemistry 23, no. 17 (2019): 1843–56. http://dx.doi.org/10.2174/1385272823666191007163310.

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Partially reduced heterocyclic compounds such as 1,4,5,6-tetrahydropyrimidines are often found to possess interesting pharmacological properties. Yet, the synthetic routes towards such systems are less developed than their fully aromatic counterparts. In this review article, the biological significance of 1,4,5,6-tetrahydropyrimidines is discussed and the existing literature reports describing various preparative routes to access 1,4,5,6-tetrahydropyrimidine derivatives have been categorically described. The focus has been expanded to present an overview of the chronological development of the

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6

Charushin, Valery N., and Henk C. van der Plas. "Ring transformations in reactions of heterocyclic compounds with nucleophiles. The conversion of 5-nitropyrimidine into pyridine derivatives by CH-acitve nitriles." Recueil des Travaux Chimiques des Pays-Bas 102, no. 7-8 (2010): 373–77. http://dx.doi.org/10.1002/recl.19831020708.

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7

Tan, Xiaojun, and Xiuhui Lu. "Ab initio study of mechanism of forming a Si-heterocyclic spiro-Sn-heterocyclic ring compound by cycloaddition reaction of Me2Si=Sn: and ethene." Progress in Reaction Kinetics and Mechanism 44, no. 2 (2019): 114–21. http://dx.doi.org/10.1177/1468678319825898.

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X2Si=Sn: (X = H, Me, F, Cl, Br, Ph, Ar, etc.) are a new chemical species. The cycloaddition reactions of X2Si=Sn: are a new field of stannylene chemistry. The mechanism of the cycloaddition reaction between singlet state Me2Si=Sn: and ethene has been investigated for the first time here using second-order Møller-Plesset perturbation theory together with the 6-311++G** basis set for C, H and Si atoms and the LanL2dz basis set for Sn atoms. From the potential energy profile, it could be predicted that the reaction has one dominant reaction channel. The reaction process presented is that the 5p u

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8

Fershtat, Leonid L., Daniil A. Chaplygin, Ivan V. Ananyev, and Nina N. Makhova. "Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans." Synthesis 52, no. 18 (2020): 2667–78. http://dx.doi.org/10.1055/s-0040-1707393.

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A novel method for the synthesis of a diverse series of functionally substituted five-membered heterocyclic compounds via atom-economic, regio-, and diastereoselective one-pot reaction cascade was developed. This approach involves a ring opening in 4-arylfuroxans to α-oximinoarylacetonitrile oxides followed by [3+2] cycloaddition to various dipolarophiles to afford multisubstituted isoxazoles and isoxazolines. Subsequent azole–azole rearrangement of (oximino)isoxazolines/-isoxazoles, which can be conducted in a one-pot manner, results into functionally substituted furazans formation. The devel

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9

Tan, Xiaojun, and Xiuhui Lu. "Ab initio study of the mechanism of formation of a spiro-Sn-heterocyclic ring compound by the cycloaddition reaction of H2C=Sn: and ethylene." Journal of the Serbian Chemical Society 84, no. 3 (2019): 293–301. http://dx.doi.org/10.2298/jsc180603072t.

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X2C=Sn: (X = H, Me, F, Cl, Br, Ph, Ar?) are new species of chemistry. The cycloaddition reactions of X2C=Sn: is a new study field of stannylene chemistry. The mechanism of cycloaddition reaction of singlet H2C=Sn: with ethylene is studied for the first time using the MP2/GENECP (C, H in 6-311++G**; Sn in LanL2dz) method in this paper. From the potential energy profile, it could be predicted that the reaction has one dominant reaction channel. The reaction rule presented is that the 5p unoccupied orbital of tin in H2C=Sn: sidewise overlaps with the bonding ? orbital of ethylene resulting in the

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10

Höpfl, Herbert, and Norberto Farfán. "Article." Canadian Journal of Chemistry 76, no. 12 (1998): 1853–59. http://dx.doi.org/10.1139/v98-192.

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Boron chelates obtained from salicylaldehyde and 2prime-hydroxyacetophenone azines are colored compounds with potential applications in analytical chemistry. Up to now these complexes have not been studied by X-ray crystallography, although two structures with a six- or a seven-membered chelate ring are possible. This contribution presents the X-ray analysis of 2prime-hydroxyacetophenone azine and its corresponding new mono(diphenylboron) chelate with a six-membered boron heterocyclic ring. With these data structural changes of the ligand on chelate formation and structural differences in comp

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11

Zhang, Qiang, Sizhe Li, Maha Hachicha, et al. "Heterocyclic Chemistry Applied to the Design of N-Acyl Homoserine Lactone Analogues as Bacterial Quorum Sensing Signals Mimics." Molecules 26, no. 17 (2021): 5135. http://dx.doi.org/10.3390/molecules26175135.

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N-acyl homoserine lactones (AHLs) are small signaling molecules used by many Gram-negative bacteria for coordinating their behavior as a function of their population density. This process, based on the biosynthesis and the sensing of such molecular signals, and referred to as Quorum Sensing (QS), regulates various gene expressions, including growth, virulence, biofilms formation, and toxin production. Considering the role of QS in bacterial pathogenicity, its modulation appears as a possible complementary approach in antibacterial strategies. Analogues and mimics of AHLs are therefore biologic

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12

Boraei, Ahmed T. A., Ahmed A. M. Sarhan, Sammer Yousuf, and Assem Barakat. "Synthesis of a New Series of Nitrogen/Sulfur Heterocycles by Linking Four Rings: Indole; 1,2,4-Triazole; Pyridazine; and Quinoxaline." Molecules 25, no. 3 (2020): 450. http://dx.doi.org/10.3390/molecules25030450.

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A new series of nitrogen and sulfur heterocyclic systems were efficiently synthesized by linking the following four rings: indole; 1,2,4-triazole; pyridazine; and quinoxaline hybrids. The strength of the acid that catalyzes the condensation of 4-amino-5-(1H-indol-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 1 with aromatic aldehydes controlled the final product. Reflux in glacial acetic acid yielded Schiff bases 2–6, whereas concentrated HCl in ethanol resulted in a cyclization product at C-3 of the indole ring to create indolo-triazolo-pyridazinethiones 7–16. This fascinating cyclization appr

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13

Tan, Xiaojun, and Xiuhui Lu. "Theoretical study of the formation of a spiro-Sn-heterocyclic compound by cycloaddition reaction of Me2C=Sn: and ethene." Heterocyclic Communications 24, no. 6 (2018): 311–15. http://dx.doi.org/10.1515/hc-2018-0129.

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AbstractX2C=Sn: compounds (X=H, Me, F, Cl, Br, Ph, Ar) are new species. The cycloaddition reactions of X2C=Sn: are also a new study field of unsaturated stannylene chemistry. The mechanism of cycloaddition reaction between singlet Me2C=Sn: and ethene was investigated for the first time using the MP2/GENECP (C, H in 6-311++G**; Sn in LanL2dz) method. From the potential energy profile, it was predicted that the reaction has one dominant channel in which the 5p unoccupied orbital of Sn: in Me2C=Sn: and theπorbital of ethene form aπ→pdonor-acceptor bond in an intermediate product. Instability of t

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14

Wu, Mengyao, Yilin Wang, Xiaojun Tan, and Jinsong Gu. "Theoretical study on the reaction between phosphacyclopropenylidene and ethylene: An alternative approach to the formation of phosphorus-bearing heterocyclic compound." Journal of the Serbian Chemical Society 85, no. 9 (2020): 1175–84. http://dx.doi.org/10.2298/jsc191217026w.

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The reaction mechanism between phosphacyclopropenylidene and ethylene has been systematically investigated at the B3LYP/6-311++G(d,p) level of theory in order to better understand the reactivity of unsaturated cyclic phosphorus-bearing carbene. Geometry optimizations and vibrational analyses have been performed for the stationary points on the potential energy surface of the system. Calculations show that the spiro bicyclic intermediate could be produced through the cycloaddition process between phosphacyclopropenylidene and ethylene initially. The reaction mechanism is illustrated with the fr

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15

Hofmann, Hans, Gerhard Löw, and Armin Haag. "Heterocyclische Siebenring-Verbindungen, XXIX [1] Bildung und Abfangreaktionen von substituierten 2,3-Dehydro- 1,5-benzodioxepinen / Heterocyclic Seven-Membered Ring Compounds, XXIX [1] Formation and Trapping Reactions of Substituted 2,3-Dehydro-1,5-benzodioxepins." Zeitschrift für Naturforschung B 40, no. 11 (1985): 1575–79. http://dx.doi.org/10.1515/znb-1985-1128.

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4-Cyano- and 4-Carbomethoxy-3,4-dihydro-2H-l,5-benzodioxepin-3-one (1a and 1b) have been converted to the corresponding enol-toluenesulfonates 2a and 2b, respectively. Reaction of 2a and 2b with base led to the heterocyclic allenes 3a resp. 3b, which could be trapped by Diels-Alder-reaction with furane, yielding the cycloadducts 4a and 4b.

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16

Wang, Yilin, Mengyao Wu, Xiaojun Tan, and Jinsong Gu. "Insights into the reaction mechanism between phosphacyclopropenylidene and methyleneimine: A theoretical study." Main Group Chemistry 19, no. 3 (2020): 237–44. http://dx.doi.org/10.3233/mgc-200906.

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The reaction mechanism between phosphacyclopropenylidene and methyleneimine has been systematically investigated at the M06–2X/6–311++G(d,p) level of theory in order to better understand the reactivity of unsaturated cyclic phosphorus-bearing carbene. Geometry optimizations and vibrational analyses have been conducted for the stationary points on the potential energy surface of the system. Calculations show that the spiro bicyclic intermediate could be produced through the cycloaddition process between phosphacyclopropenylidene and methyleneimine initially. The reaction mechanism is illustrate

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17

Jabbour, Adel, Reem Smoum, Khuloud Takrouri, et al. "Pharmacologically active boranes." Pure and Applied Chemistry 78, no. 7 (2006): 1425–53. http://dx.doi.org/10.1351/pac200678071425.

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Novel methods are described for the preparation of alkyldimethylamine cyanoboranes and β-hydroxylalkyldimethylamine cyanoboranes by C-lithiation of trimethylamine cyanoboranes followed by reaction with alkyl halides, aldehydes, and ketones. Lithiation of the monobromo derivatives of amine cyanoboranes led to the synthesis of the first examples of diborane derivatives of amine cyanoboranes. Bromo derivatives of amine cyanoboranes and amine carboxyboranes have been synthesized by new simple and efficient methods. Amine fluorocyanoboranes and amine fluorocarboxyboranes, new classes of compounds,

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18

Masdeu, Carme, Maria Fuertes, Endika Martin-Encinas, et al. "Fused 1,5-Naphthyridines: Synthetic Tools and Applications." Molecules 25, no. 15 (2020): 3508. http://dx.doi.org/10.3390/molecules25153508.

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Heterocyclic nitrogen compounds, including fused 1,5-naphthyridines, have versatile applications in the fields of synthetic organic chemistry and play an important role in the field of medicinal chemistry, as many of them have a wide range of biological activities. In this review, a wide range of synthetic protocols for the construction of this scaffold are presented. For example, Friedländer, Skraup, Semmlere-Wolff, and hetero-Diels-Alder, among others, are well known classical synthetic protocols used for the construction of the main 1,5-naphthyridine scaffold. These syntheses are classified

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19

Kore, Nitin, and Pavel Pazdera. "New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for “Click” Chemistry: Synthesis of 1,2,3-Triazole and Novel Synthesis of 1,2,3-Triazol-5-amine." Current Organic Synthesis 15, no. 4 (2018): 552–65. http://dx.doi.org/10.2174/1570179415666180110152642.

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Aim and Objective: The aim of our work is to demonstrate catalytic application of our previously reported simple Cu(I) ion supported on weakly acidic polyacrylate resin for Azide-Alkyne cycloaddition (CuAAC), Azide-Nitrile cycloaddition and in synthesis of 1-azido-4-methoxybenzene. Material and Method: To investigate the catalytic ability of title Cu(I) catalyst we performed the reaction of different aryl azide with a broader spectrum of different terminal alkyne and nitrile compounds. Results: The title supported Cu(I) catalyzes cycloaddition reactions of aryl azide with aliphatic, aromatic,

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20

Nagaraju, Pallava, Pedavenkatagari Narayana Reddy, Pannala Padmaja, and Vinod G. Ugale. "Synthesis, Antiproliferative Activity and Molecular Docking of New Thiazole/Benzothiazole Fused Pyranopyrimidine Derivatives." Letters in Organic Chemistry 17, no. 12 (2020): 951–58. http://dx.doi.org/10.2174/1570178617666200319114611.

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A new class of 4H,5H-benzo[4,5]thiazolo[3,2-a]pyrano[2,3-d]pyrimidin-5-one and 5H,6Hpyrano[ 2,3-d]thiazolo[3,2-a]pyrimidin-5-one derivatives were synthesized via the one-pot threecomponent reaction of 2-hydroxy-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one and 7-hydroxy-5Hthiazolo[ 3,2-a]pyrimidin-5-one to various aromatic aldehydes and malononitrile. This domino transformation involves the formation of pyranopyrimidine ring by the formation of three C–C bonds and one C– O bond a single synthetic operation. As the products precipitate out of the reaction, simple filtration is enough to gather th

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21

Sharma, Amit, and Ashok Kumar Singh. "Synthesis, Characterization and Biological Screening of Azepine Derivative: 2-hydroxy-1,3-di(naphthalene-2-yl)-1H-benzo[b]azepine-5(4H)one." Journal of Nepal Chemical Society 42, no. 1 (2021): 75–79. http://dx.doi.org/10.3126/jncs.v42i1.35336.

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The synthesis of unsaturated heterocyclic compounds containing nitrogen atoms in the ring is very important due to its various biological application in the pharmaceutical industry. Azepine derivatives find numerous application almost every field in medicinal chemistry and some of its are commercially available as drugs. The two-component of azepine derivatives were synthesized by using the aniline and maleic anhydride as a starting material followed by condensation with sodium borohydride in presence of dry benzene, subsequently cyclization by polyphosphoric acid then, finally by an addition

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22

Li, Xuan, Yixiang Gao, Chenpeng Zuo, et al. "The Gas-Phase Formation Mechanism of Dibenzofuran (DBF), Dibenzothiophene (DBT), and Carbazole (CA) from Benzofuran (BF), Benzothiophene (BT), and Indole (IN) with Cyclopentadienyl Radical." International Journal of Molecular Sciences 20, no. 21 (2019): 5420. http://dx.doi.org/10.3390/ijms20215420.

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Benzofuran (BF), benzothiophene (BT), indole (IN), dibenzofuran (DBF), dibenzothiophene (DBT), and carbazole (CA) are typical heterocyclic aromatic compounds (NSO-HETs), which can coexist with polycyclic aromatic hydrocarbons (PAHs) in combustion and pyrolysis conditions. In this work, quantum chemical calculations were carried out to investigate the formation of DBF, DBT, and CA from the reactions of BF, BT, and IN with a cyclopentadienyl radical (CPDyl) by using the hybrid density functional theory (DFT) at the MPWB1K/6-311+G(3df,2p)//MPWB1K/6-31+G(d,p) level. The rate constants of crucial e

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23

Banik, Bimal Krishna, Biswa Mohan Sahoo, Bera Venkata Varaha Ravi Kumar, et al. "Green Synthetic Approach: An Efficient Eco-Friendly Tool for Synthesis of Biologically Active Oxadiazole Derivatives." Molecules 26, no. 4 (2021): 1163. http://dx.doi.org/10.3390/molecules26041163.

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Green synthetic protocol refers to the development of processes for the sustainable production of chemicals and materials. For the synthesis of various biologically active compounds, energy-efficient and environmentally benign processes are applied, such as microwave irradiation technology, ultrasound-mediated synthesis, photo-catalysis (ultraviolet, visible and infrared irradiation), molecular sieving, grinding and milling techniques, etc. Thesemethods are considered sustainable technology and become valuable green protocol to synthesize new drug molecules as theyprovidenumerous benefits over

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24

Saokham, Phennapha, Kanokporn Burapapadh, Pitsiree Praphanwittaya та Thorsteinn Loftsson. "Characterization and Evaluation of Ternary Complexes of Ascorbic Acid with γ-Cyclodextrin and Poly(vinyl Alcohol)". International Journal of Molecular Sciences 21, № 12 (2020): 4399. http://dx.doi.org/10.3390/ijms21124399.

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Ascorbic acid (AA) is a general antioxidant used in aqueous pharmaceutical formulations. However, in aqueous solutions, AA is unstable and easily oxidized when exposed to air, light and/or heat. Cyclodextrins are well known for their ability to form inclusion complexes with various compounds to improve their solubility and stability. Previous studies demonstrate that cyclodextrins preserve the antioxidant capacity of AA but data for γ-cyclodextrin (γCD) have not been reported. Poly(vinyl alcohol) (PVA) is a hydrophilic polymer widely used as a drug matrix in various pharmaceutical fields, but

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25

D'Auria, Maurizio. "The photochemical Isomerization of Hexatomic Heterocyclic Compounds." Current Organic Chemistry 25 (July 6, 2021). http://dx.doi.org/10.2174/1385272825666210706124855.

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: The photochemical isomerization of hexatomic heterocyclic compounds has been discussed. The attention was focused on the mono- and dinitrogen hexatomic heterocycles. To justify the photochemical isomerization of pyridines, Dewar isomers, azaprismane, and azaprefulvene derivatives have been proposed. The photoisomerization of pyridinium salts requires a ring reduction with the formation of arizines. Pryridium ylides gave photoisomerization reaction trough the formation of the corresponding azirines, while pyridinium N-oxide required to react the formation of the corresponding oxaziridines. Th

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26

Banik, Bimal Krishna, Biswa Mohan Sahoo, BVV Ravi Kumar, and Krishna Chandra Panda. "Microwave Induced Green chemistry approach towards synthesis of heterocyclic compounds via C-N Bond Forming Reactions." Current Microwave Chemistry 08 (September 23, 2021). http://dx.doi.org/10.2174/2213335608666210923144201.

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: The synthesis of heterocyclic compounds via carbon-nitrogen (C-N) bond formation reaction is considered as an emerged and efficient protocol in the field of synthetic chemistry. The C–N bond-forming reactions can proceed through condensation, coupling, ring-opening, cyclization or ring closure process etc. The reactivity pattern of these reactions mainly depends upon the reaction conditions as well as the type of catalysts and reacting substances that are associated with the synthesis of heterocyclic compounds containing the C-N system including pyrazole, imidazole, pyridine, pyrimidine, thi

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27

Tabassum, Rukhsana, Muhammad Ashfaq, and Hiroyuki Oku. "Recent Advances in Transition Metal Mediated Synthetic Approaches to Quinoline Derivatives." Letters in Organic Chemistry 17 (October 20, 2020). http://dx.doi.org/10.2174/1570178617999201020215632.

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Abstract:: Synthesis of heterocyclic compounds containing quinoline scaffold attracted a significant attention of organic chemists due to their importance as therapeutic agent in pharmaceutical industry. Quinolone molecule exhibit extensive biological activities a few of which are antiviral, anti-inflammatory antibacterial, antifungal, antiproliferative, anthelmintic and anticonvulsant. A variety of synthetic routes has been developed for construction compounds bearing quinoline nucleus due to its broad spectrum of pharmacological activities. This review describes recent development in transit

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28

Nagaraju, Pallava, Pedavenkatagari Narayana Reddy, Pannala Padmaja, and Vinod G. Ugale. "Microwave assisted synthesis of thiazole/benzothiazole fused pyranopyrimidine derivatives and evaluation of their biological activity." Letters in Organic Chemistry 17 (May 17, 2020). http://dx.doi.org/10.2174/1570178617999200517130138.

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: A new class of phenylbenzo[4,5]thiazolo[3,2-a]pyrano[2,3-d]pyrimidin-5-one and pyrano[2,3-d]thiazolo[3,2-a]pyrimidine-5-one derivatives have been synthesized via one pot three-component reaction of 2-hydroxy-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one and 7- hydroxy-5H-thiazolo[3,2-a]pyrimidin-5-one with various aromatic aldehydes and (E)-N-methyl-1-(methylthio)-2-nitroethenamine under microwave irradiation. This transformation involves formation of thiazole or benzothiazole fused pyranopyrimidinone ring by creation of two C–C bonds and one C–O bond in a single synthetic operation. This rapi

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