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Journal articles on the topic 'Polyheterocyclics'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 May 2024

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1

Lebedev, Rodion, Dmitry Dar’in, Grigory Kantin, Olga Bakulina, and Mikhail Krasavin. "One-Pot Sequence of Staudinger/aza-Wittig/Castagnoli–Cushman Reactions Provides Facile Access to Novel Natural-like Polycyclic Ring Systems." Molecules 27, no. 23 (2022): 8130. http://dx.doi.org/10.3390/molecules27238130.

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Realization of the one-pot Staudinger/aza-Wittig/Castagnoli–Cushman reaction sequence for a series of azido aldehydes and homophthalic anhydrides is described. The reaction proceeded at room temperature and delivered novel polyheterocycles related to the natural product realm in high yields and high diastereoselectivity. The methodology has been extended to three other cyclic anhydrides. These further unravel the potential of the Castagnoli–Cushman reaction in generating polyheterocyclic molecular scaffolds.

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2

Blanco-Carapia, Roberto E., Enrique A. Aguilar-Rangel, Mónica A. Rincón-Guevara, Alejandro Islas-Jácome, and Eduardo González-Zamora. "Synthesis of New Polyheterocyclic Pyrrolo[3,4-b]pyridin-5-ones via an Ugi-Zhu/Cascade/Click Strategy." Molecules 28, no. 10 (2023): 4087. http://dx.doi.org/10.3390/molecules28104087.

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A diversity-oriented synthesis (DOS) of two new polyheterocyclic compounds was performed via an Ugi-Zhu/cascade (N-acylation/aza Diels-Alder cycloaddition/decarboxylation/dehydration)/click strategy, both step-by-step to optimize all involved experimental stages, and in one pot manner to evaluate the scope and sustainability of this polyheterocyclic-focused synthetic strategy. In both ways, the yields were excellent, considering the high number of bonds formed with release of only one carbon dioxide and two molecules of water. The Ugi-Zhu reaction was carried out using the 4-formylbenzonitrile

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3

Beduru, Srinivas, and Andrei G. Kutateladze. "Complexity-Building ESIPT-Assisted Synthesis of Fused Polyheterocyclic Sulfonamides." Molecules 28, no. 18 (2023): 6549. http://dx.doi.org/10.3390/molecules28186549.

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Excited State Intramolecular Proton Transfer (ESIPT), originally discovered and explored in depth in a number of extensive photophysical studies, is more recently rediscovered as a powerful synthetic tool, offering rapid access to complex polyheterocycles. In our prior work we have employed ESIPT in aromatic o-keto amines and amides, leading to diverse primary photoproducts—complex quinolinols or azacanes possessing a fused lactam moiety—which could additionally be modified in short, high-yielding postphotochemical reactions to further grow complexity of the heterocyclic core scaffold and/or t

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4

Horsten, Tomas, and Wim Dehaen. "4,5,6,7-Tetrahydroindol-4-Ones as a Valuable Starting Point for the Synthesis of Polyheterocyclic Structures." Molecules 26, no. 15 (2021): 4596. http://dx.doi.org/10.3390/molecules26154596.

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This review focuses on the synthesis of polyheterocyclic structures with a variety of medicinal and optoelectronic applications, starting from readily available 4,5,6,7-tetrahydroindol-4-one analogs. First, routes toward the 4,5,6,7-tetrahydroindol-4-one starting materials are summarized, followed by synthetic pathways towards polyheterocyclic structures which are categorized based on the size and attachment point of the newly formed (hetero)cyclic ring.

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5

Aksenov, Nicolai A., Alexander V. Aksenov, Nikita K. Kirilov, et al. "Nitroalkanes as electrophiles: synthesis of triazole-fused heterocycles with neuroblastoma differentiation activity." Organic & Biomolecular Chemistry 18, no. 34 (2020): 6651–64. http://dx.doi.org/10.1039/d0ob01007c.

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6

Li, Yunhe, та Xiang Zhao. "Gold-catalyzed domino cyclization to diverse polyheterocyclic frameworks: mechanism, origin of the cooperative hydrogen bond, and role of π-stacking interactions". Catalysis Science & Technology 10, № 12 (2020): 4109–18. http://dx.doi.org/10.1039/d0cy00746c.

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7

Barroso, Raquel, María-Paz Cabal, Azucena Jiménez, and Carlos Valdés. "Cascade and multicomponent synthesis of structurally diverse 2-(pyrazol-3-yl)pyridines and polysubstituted pyrazoles." Organic & Biomolecular Chemistry 18, no. 8 (2020): 1629–36. http://dx.doi.org/10.1039/c9ob02691f.

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A wide diversity of polyheterocyclic systems including polysubstituted pyrazoles and pyridopyrazole polydentate ligands are readily assembled through cascade multicomponent processes from terminal alkynes and N-tosylhydrazones.

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8

Li, Yunhe, and Xiang Zhao. "Assessing counterion effects in gold-catalyzed domino spirocyclization: an industrial perspective on hydrogen bonding." Physical Chemistry Chemical Physics 22, no. 35 (2020): 19606–12. http://dx.doi.org/10.1039/d0cp03367g.

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Different roles of some hydrogen bonding in gold-catalyzed ipso-cyclization to diverse polyheterocyclic frameworks are exposed. The correlation between hydrogen bonding parameters and chemoselectivity is determined.

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9

Palanivel, Lakshmanan, and Vasuki Gnanasambandam. "Diversity oriented multi-component reaction (DOS–MCR) approach to access natural product analogues: regio- and chemo-selective synthesis of polyheterocyclic scaffolds via one-pot cascade reactions." Organic & Biomolecular Chemistry 18, no. 16 (2020): 3082–92. http://dx.doi.org/10.1039/d0ob00368a.

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10

García-González, Ma Carmen, Eduardo Hernández-Vázquez, Raúl E. Gordillo-Cruz, and Luis D. Miranda. "Ugi-derived dehydroalanines as a pivotal template in the diversity oriented synthesis of aza-polyheterocycles." Chemical Communications 51, no. 58 (2015): 11669–72. http://dx.doi.org/10.1039/c5cc02927a.

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Various readily available, Ugi-derived dehydroalanines were used as pivotal templates to easily and efficiently assemble diverse pharmacologically important polyheterocyclic systems through cascade palladium-catalyzed C–C bond formation processes.

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11

Li, Xiao-Yun, Yan Liu, Xiao-Lan Chen та ін. "6π-Electrocyclization in water: microwave-assisted synthesis of polyheterocyclic-fused quinoline-2-thiones". Green Chemistry 22, № 14 (2020): 4445–49. http://dx.doi.org/10.1039/c9gc04445k.

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Microwave-assisted synthesis of polyheterocyclic-fused quinoline-2-thiones through the annulation of ortho-heteroaryl anilines and CS<sub>2</sub> was realized in water without using any catalysts and additives.

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12

Wudl, Fred. "Chemistry of Organic Polyheterocyclic Conductors." Israel Journal of Chemistry 27, no. 4 (1986): 289–92. http://dx.doi.org/10.1002/ijch.198600044.

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13

Zhang, Yan-Yan, Yin Wei, Xiang-Ying Tang, and Min Shi. "Dual-role of PtCl2 catalysis in the intramolecular cyclization of (hetero)aryl-allenes for the facile construction of substituted 2,3-dihydropyrroles and polyheterocyclic skeletons." Chemical Communications 53, no. 44 (2017): 5966–69. http://dx.doi.org/10.1039/c7cc01684k.

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A novel PtCl<sub>2</sub>-catalyzed cyclization of (hetero)aryl-allenes has been developed, providing controllable and facile synthesis of substituted 2,3-dihydropyrroles and polyheterocyclic skeletons in moderate to good yields.

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14

McFadden, Timothy Patrick, Chideraa Iheanyi Nwachukwu, and Andrew George Roberts. "An amine template strategy to construct successive C–C bonds: synthesis of benzo[h]quinolines by a deaminative ring contraction cascade." Organic & Biomolecular Chemistry 20, no. 7 (2022): 1379–85. http://dx.doi.org/10.1039/d1ob02245h.

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We report a strategy to build, cyclize, and excise nitrogen from tertiary amines for the synthesis of polyheterocyclic aromatics. A developed deaminative ring contraction cascade reaction is useful for the synthesis of substituted benzoquinolines.

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15

Mishra, Pawan K., and Akhilesh K. Verma. "Metal-free regioselective tandem synthesis of diversely substituted benzimidazo-fused polyheterocycles in aqueous medium." Green Chemistry 18, no. 23 (2016): 6367–72. http://dx.doi.org/10.1039/c6gc02330d.

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16

He, Yi, Danjun Wu, Zhenghua Li, Koen Robeyns, Luc Van Meervelt, and Erik V. Van der Eycken. "Facile construction of diverse polyheterocyclic scaffolds via gold-catalysed dearomative spirocyclization/1,6-addition cascade." Organic & Biomolecular Chemistry 17, no. 25 (2019): 6284–92. http://dx.doi.org/10.1039/c9ob01299k.

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A post-Ugi gold-catalysed chemo- and diastereo-selective cascade dearomative spirocyclization/1,6-addition sequence is disclosed for the facile synthesis of diverse fused polyheterocyclic scaffolds bearing indole, pyrrole, benzothiophene, furan or electron-rich arene cores.

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17

Darawsheh, M. D., L. A. Barrios, O. Roubeau, S. J. Teat, and G. Aromí. "Guest-tuned spin crossover in flexible supramolecular assemblies templated by a halide (Cl−, Br− or I−)." Chemical Communications 53, no. 3 (2017): 569–72. http://dx.doi.org/10.1039/c6cc08906b.

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A supramolecular dimer of spin-crossover [FeL<sub>3</sub>]<sup>2+</sup> complexes, L, being a polyheterocyclic ligand, encapsulates halides to form [X@[FeL<sub>3</sub>]<sub>2</sub>]<sup>3+</sup> cations with tunable magnetic properties.

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18

Prieschl, Dominic, Merle Arrowsmith, Maximilian Dietz, Anna Rempel, Marcel Müller та Holger Braunschweig. "Synthesis of polyheterocyclic 1,1-diboryltriazenes by γ-nitrogen insertion of azides into activated B–B single bonds". Chemical Communications 56, № 42 (2020): 5681–84. http://dx.doi.org/10.1039/d0cc02305a.

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The γ-nitrogen insertion of arylazides into the B–B bond of electron-rich cyclic μ-hydridodiboranes yields unsymmetrical polyheterocyclic 1,1-diboryltriazenes, which may undergo further NHC ring expansion/fusion and thermally induced loss of N<sub>2</sub>.

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19

Ibarra, Ilich A., Alejandro Islas-Jácome, and Eduardo González-Zamora. "Synthesis of polyheterocyclesviamulticomponent reactions." Organic & Biomolecular Chemistry 16, no. 9 (2018): 1402–18. http://dx.doi.org/10.1039/c7ob02305g.

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20

Li, Zhenghua, Nandini Sharma, Upendra K. Sharma, Jeroen Jacobs, Luc Van Meervelt, and Erik V. Van der Eycken. "Ligand-controlled product selectivity in palladium-catalyzed domino post-Ugi construction of (spiro)polyheterocycles." Chemical Communications 52, no. 32 (2016): 5516–19. http://dx.doi.org/10.1039/c6cc00784h.

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21

Otani, Takashi, Yumiko Tamai, Kazunori Seki, Tomohiro Kikuchi, Taiichiro Miyazawa та Takao Saito. "Stereo-controlled synthesis of polyheterocycles via the diene-transmissive hetero-Diels–Alder reaction of β,γ-unsaturated α-keto esters". Organic & Biomolecular Chemistry 13, № 21 (2015): 5875–79. http://dx.doi.org/10.1039/c5ob00503e.

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22

Prasad, Sure Siva, Dirgha Raj Joshi, Jeong Hwa Lee, and Ikyon Kim. "One-pot access to 2-amino-3-arylbenzofurans: direct entry to polyheterocyclic chemical space." Organic & Biomolecular Chemistry 18, no. 40 (2020): 8119–40. http://dx.doi.org/10.1039/d0ob01715a.

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23

Dubois, J. C., O. Sagnes, and F. Henry. "Polyheterocyclic conducting polymers and composites derivates." Synthetic Metals 28, no. 1-2 (1989): 871–78. http://dx.doi.org/10.1016/0379-6779(89)90616-4.

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24

Galenko, Ekaterina E., Firuza M. Shakirova, Vladimir A. Bodunov, Mikhail S. Novikov, and Alexander F. Khlebnikov. "1-(2H-Azirine-2-carbonyl)benzotriazoles: building blocks for the synthesis of pyrrole-containing heterocycles." Organic & Biomolecular Chemistry 18, no. 12 (2020): 2283–96. http://dx.doi.org/10.1039/d0ob00206b.

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25

Cheng, Chao, Wen-Wen Chen, Bin Xu, and Ming-Hua Xu. "Intramolecular cross dehydrogenative coupling of 4-substituted coumarins: rapid and efficient access to coumestans and indole[3,2-c]coumarins." Organic Chemistry Frontiers 3, no. 9 (2016): 1111–15. http://dx.doi.org/10.1039/c6qo00270f.

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A palladium-catalyzed highly efficient and atom-economical intramolecular cross dehydrogenative coupling (CDC) reaction to access fused polyheterocycles containing a coumarin nucleus has been developed.

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26

Chen, Xiaoyan, Hao Zhou, and Zhiyuan Chen. "Pd/P/dba-Promoted cascade annulations to produce fused medium-sized sulfoximine polyheterocycles." Organic Chemistry Frontiers 6, no. 19 (2019): 3415–19. http://dx.doi.org/10.1039/c9qo00880b.

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The Pd-catalyzed multicomponent reactions of NH-sulfoximine, aryl iodide and norbornadiene (NBD) are reported to chemoselectively produce fused medium-sized sulfoximine polyheterocycles in good to excellent yields.

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27

Pandey, Anand Kumar, Rashmi Sharma, Awantika Singh, et al. "Synthesis of biologically active pyridoimidazole/imidazobenzothiazole annulated polyheterocycles using cyanuric chloride in water." RSC Adv. 4, no. 51 (2014): 26757–70. http://dx.doi.org/10.1039/c4ra03415e.

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28

Wu, Le, Piao He, Zhimin Li, et al. "Synthesis of 3,5-ditetrazolyl-1,2,4-triazole-based complexes: a strategy for developing C–N-linked triheterocyclic energetic compounds." New Journal of Chemistry 43, no. 12 (2019): 4975–79. http://dx.doi.org/10.1039/c8nj06556j.

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Two complexes based on the novel C–N-linked triheterocyclic compound 3,5-ditetrazolyl-1,2,4-triazole (DTT) were reported for the first time. The present study has contributed to the field of C–N-linked polyheterocyclic systems and has provided a new insight into the design and synthesis of new energetic materials.

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29

Preston, J., Y. Tropsha, and J. W. Trexler. "Thermoplastic polyheterocycles. I: Polyalkylene-benzoxazoles." Polymer Engineering and Science 34, no. 4 (1994): 301–4. http://dx.doi.org/10.1002/pen.760340411.

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30

Preston, J., and Y. Tropsha. "Thermoplastic polyheterocycles. II: Polyalkylene-imides." Polymer Engineering and Science 34, no. 4 (1994): 305–7. http://dx.doi.org/10.1002/pen.760340412.

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31

Kaur, Navjeet. "Ionic Liquid Promoted Eco-friendly and Efficient Synthesis of Six-membered Npolyheterocycles." Current Organic Synthesis 15, no. 8 (2018): 1124–46. http://dx.doi.org/10.2174/1570179415666180903102542.

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Background: The synthesis of N-polyheterocycles by environmentally benign method is highly attractive but challenging proposition. New strategies have been developed for the preparation of polycyclic heterocycles in the last decades. In this review article, the synthesis of nitrogen containing six-membered polycyclic heterocyclic compounds is presented with the application of ionic liquids. This contribution focuses on the literature related to the total synthesis of six-membered N-polyheterocycles. Objective: Ionic liquids not only acted as environmentally benign reaction media but also as ca

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32

Blackham, Emma E., Jonathan P. Knowles, Jonathan Burgess, and Kevin I. Booker-Milburn. "Combining photochemistry and catalysis: rapid access to sp3 – rich polyheterocycles from simple pyrroles." Chemical Science 7, no. 3 (2016): 2302–7. http://dx.doi.org/10.1039/c5sc04062k.

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The powerful combination of photochemistry and catalysis transforms simple pyrroles into complex polycyclic structures in just two steps. Initial formation of highly reactive aziridines enables new Pd-catalysed cascade sequences, forming a range of polyheterocycles including tricyclic β-lactams.

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33

Dotsenko, Victor V., Elena A. Chigorina, and Sergey G. Krivokolysko. "Synthesis of 7-thia-1,4,6,8-tetraazabenzo[de]anthracenes." Proceedings 9, no. 1 (2018): 31. http://dx.doi.org/10.3390/ecsoc-22-05682.

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New polyheterocyclic ensembles of 8,9,10,11-tetrahydro-7-thia-1,4,6,8-tetraazabenzo[de]anthracenes were prepared by reaction of easily available 5Н-pyrido[2’,3’:2,3]thiopyrano[4,5-b]pyridines with Ас2О or acyl chlorides. The starting 5Н-pyrido[2’,3’:2,3]thiopyrano[4,5-b]pyridines were prepared by reaction of N-methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates with malononitrile dimer.

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34

Ziarani, Ghodsi Mohammadi, Mahdieh Khademi, Fatemeh Mohajer, Sangeeta Yadav, and Ravi Tomar. "Recent Advances in the Application of Barbituric Acid Derivatives in Multicomponent Reactions." Current Organic Chemistry 26, no. 2 (2022): 162–88. http://dx.doi.org/10.2174/1385272826666211229150318.

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Abstract: Barbituric acid is a pyrimidine heterocyclic organic compound, which is pharmacologically active. It is important to build structures containing various medicinal activities. This compound attracts the scientific research community in organic synthesis. It can be used in the synthesis of polyheterocyclic, natural, medicinal compounds, and organic sensors. Herein, the utilization of barbituric or thiobarbituric acid in multicomponent reactions is reported from 2016-2021 in this manuscript.

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35

Wang, Qian, Jesse Tuinhof, Kumchok C. Mgimpatsang, Katarzyna Kurpiewska, Justyna Kalinowska-Tluscik, and Alexander Dömling. "Copper-Catalyzed Modular Assembly of Polyheterocycles." Journal of Organic Chemistry 85, no. 15 (2020): 9915–27. http://dx.doi.org/10.1021/acs.joc.0c01238.

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36

Wang, Yading, M. F. Rubner, and L. J. Buckley. "Stability studies of electrically conducting polyheterocycles." Synthetic Metals 41, no. 3 (1991): 1103–8. http://dx.doi.org/10.1016/0379-6779(91)91562-o.

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37

Hassikou, Amina, Ghita Amine Benabdallah, Mohammed Naceur Dinia, Khalid Bougrin, and Mohamed Soufiaoui. "ChemInform Abstract: Synthesis of Novel Polyheterocycles." ChemInform 32, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.200149089.

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38

Benzi, Alice, Lara Bianchi, Gianluca Giorgi, et al. "An Easy Access to Furan-Fused Polyheterocyclic Systems." Molecules 27, no. 10 (2022): 3147. http://dx.doi.org/10.3390/molecules27103147.

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Nitrostilbenes characterized by two different or differently substituted aryl moieties can be obtained from the initial ring-opening of 3-nitrobenzo[b]thiophene with amines. Such versatile building blocks couple the well-recognized double electrophilic reactivity of the nitrovinyl moiety (addition to the double bond, followed by, e.g., intramolecular replacement of the nitro group) with the possibility to exploit a conjugated system of double bonds within an electrocyclization process. Herein, nitrostilbenes are reacted with different aromatic enols provided by a double (carbon and oxygen) nuc

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39

Velikorodov, A. V., N. N. Stepkina, M. A. Polovinkina, and V. P. Osipova. "Synthesis of New Polyheterocyclic Compounds Based on Chalcones." Russian Journal of Organic Chemistry 55, no. 7 (2019): 999–1004. http://dx.doi.org/10.1134/s1070428019070157.

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40

Sagnes, O., D. Broussox, and F. Henry. "Polyheterocyclic conducting polymers composite compatability and conducting behaviour." Synthetic Metals 41, no. 3 (1991): 989. http://dx.doi.org/10.1016/0379-6779(91)91542-i.

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41

Fern�ndez, David, Abderaouf Ahaidar, Gerardo Danel�n, et al. "Synthesis of Polyheterocyclic Nitrogen-Containing Marine Natural Products." Monatshefte f�r Chemie / Chemical Monthly 135, no. 6 (2004): 615–27. http://dx.doi.org/10.1007/s00706-003-0119-9.

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42

Barsegyan, Yana A., Vladimir V. Baranov, and Angelina N. Kravchenko. "Glycolurils in the synthesis of fused polyheterocyclic compounds." Chemistry of Heterocyclic Compounds 53, no. 2 (2017): 116–22. http://dx.doi.org/10.1007/s10593-017-2029-5.

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43

Tripathi, Krishna N., Avinash H. Bansode, and Ravi P. Singh. "Palladium-Catalyzed Oxidative Annulation of Pyrrolylalkyl-1H-azoles: Towards the Synthesis of Polyheterocyclic Arenes." Synthesis 52, no. 05 (2019): 719–26. http://dx.doi.org/10.1055/s-0039-1691492.

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A highly efficient and regioselective palladium-catalyzed annulation protocol for a series of linear and terminally substituted 1,2- and 1,3-di(heteroaryl)alkanes to the corresponding polyheterocyclic arenes is reported. Herein, intramolecular oxidative coupling involving double C(sp2)–H bond functionalization provides a feasible access to biheteroaryl systems annulated to a six-membered ring. The methodology is not restricted to six-membered annulations and was extended to the synthesis of compounds with a seven-membered ring and biheteroaryl core.

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44

Mittersteiner, Mateus, Nilo Zanatta, Helio G. Bonacorso та Marcos A. P. Martins. "Brominated β-Alkoxyvinyl Trihalomethyl Ketones as Promising Synthons in Heterocyclic Synthesis". Synthesis 52, № 14 (2020): 2008–16. http://dx.doi.org/10.1055/s-0039-1690890.

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5-Bromo- and 5,5-dibromo-1,1,1-trihalo-4-methoxypent-3-en-2-ones (brominated enones) have proven to be attractive building blocks for the construction of heterocyclic and polyheterocyclic compounds bearing a trihalomethyl moiety through interesting cyclocondensation, alkylation, and cycloaddition reactions. This review compiles all of the reactions conducted with these brominated enones since they were first disclosed in 2001.1 Introduction2 Synthesis and Initial Applications3 Synthesis Using First-Generation Intermediates4 Synthesis Using Second-Generation Intermediates5 Synthesis Using Third

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45

Dawood, Kamal M., and Bakr F. Abdel-Wahab. "Synthetic routes to benzimidazole-based fused polyheterocycles." Arkivoc 2010, no. 1 (2010): 333–89. http://dx.doi.org/10.3998/ark.5550190.0011.109.

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46

Pomerantz, Martin, Benjamin Chaloner-Gill, Larry O. Harding, John J. Tseng, and Wendy J. Pomerantz. "New processable low band-gap, conjugated polyheterocycles." Synthetic Metals 55, no. 2-3 (1993): 960–65. http://dx.doi.org/10.1016/0379-6779(93)90182-v.

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47

Sai Reddy, D., Olga A. Mukhina, W. Cole Cronk, and Andrei G. Kutateladze. "Polyheterocycle-carbohydrate chimeras: photoassisted synthesis of 2,5-epoxybenzoxacines and 2,5-epoxybenzazocine scaffolds and their postphotochemical hydroxylations." Pure and Applied Chemistry 89, no. 2 (2017): 259–68. http://dx.doi.org/10.1515/pac-2016-0915.

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AbstractPhotoassisted synthesis of complex polyheterocyclic molecular architectures via excited state intramolecular proton transfer (ESIPT) is for the first time implemented for the reactions of o-keto phenols. This adds the 2,5-epoxybenzoxacine core to the previously obtained 2,5-epoxybenzazocine cores and offers rapid access to primary photoproducts which lend themselves to diverse yet simple postphotochemical modifications to further grow the complexity of the target structures, specifically – access to polyheterocycle-carbohydrate chimeras containing up to five contiguous stereogenic cent

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48

Wang, Zhen-Hua, Tong Zhang, Li-Wen Shen, et al. "Diverse Synthesis of Fused Polyheterocyclic Compounds via [3 + 2] Cycloaddition of In Situ-Generated Heteroaromatic N-Ylides and Electron-Deficient Olefins." Molecules 28, no. 11 (2023): 4410. http://dx.doi.org/10.3390/molecules28114410.

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[3 + 2] Cycloaddition reactions of heteroaromatic N-ylides with electron-deficient olefins have been developed. The heteroaromatic N-ylides, in situ generated from N-phenacylbenzothiazolium bromides, can smoothly react with maleimides under very mild conditions, affording fused polycyclic octahydropyrrolo[3,4-c]pyrroles in good-to-excellent isolated yields. This reaction concept could also be extended to 3-trifluoroethylidene oxindoles and benzylidenemalononitriles as electron-deficient olefins for accessing highly functionalized polyheterocyclic compounds. A gram-scale experiment was also car

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Dawood, Kamal M., Eman A. Ragab, and Ahmad M. Farag. "Polyheterocyclic systems incorporating pyrazole, thiophene, thiazole, and thiadiazole moieties." Journal of Chemical Research (Miniprint) 2003, no. 11 (2003): 685–86. http://dx.doi.org/10.3184/030823503322862508.

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50

Dawood, Kamal M., Eman A. Ragab, and Ahmad M. Farag. "Polyheterocyclic systems incorporating pyrazole, thiophene, thiazole, and thiadiazole moieties." Journal of Chemical Research 2003, no. 11 (2003): 685–86. http://dx.doi.org/10.3184/030823403322862914.

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