Crossref Cited-by Linking logo

Collect. Czech. Chem. Commun. 1988, 53, 1534-1538
https://doi.org/10.1135/cccc19881534

Nitriles in heterocyclic synthesis: Novel syntheses of benzo[b]pyrans, naphtho[1,2-b]pyrans, naphtho[2,1-b]pyrans, pyrano[3,2-h]quinolines and pyrano[3,2-c]quinolines

Abdel Ghani A. Elagameya, Salah Z. Sawllima, Fathy M. A. El-Taweela and Mohamed H. Elnagdib

a Chemistry Department, Mansoura University, Damietta, Egypt
b Chemistry Department, Cairo University, Giza, Egypt

Crossref Cited-by Linking

  • Dotsenko V. V, Khalatyan K. V, Russkikh A. A, Varzieva E. A, Kramareva D. A, Vasilin V. K, Aksenov N. A, Aksenova I. V: Synthesis and some properties of 2-amino-4-aryl-6-hexyl7-hydroxy-4h-chromene-3-carbonitriles. Žurnal obŝej himii 2023, 93, 31. <https://doi.org/10.31857/S0044460X23010043>
  • Dotsenko V. V., Khalatyan K. V., Russkikh A. A., Varzieva E. A., Kramareva D. A., Vasilin V. K., Aksenov N. A., Aksenova I. V.: Synthesis and Some Properties of 2-Amino-4-aryl-6-hexyl-7-hydroxy-4H-chromene-3-carbonitriles. Russ J Gen Chem 2022, 92, 2850. <https://doi.org/10.1134/S1070363222120374>
  • Aly Ashraf A., El-Sheref Essmat M., Mourad Aboul-Fetouh E., Bakheet Momtaz E. M., Bräse Stefan: 4-Hydroxy-2-quinolones: syntheses, reactions and fused heterocycles. Mol Divers 2020, 24, 477. <https://doi.org/10.1007/s11030-019-09952-5>
  • Mkaouar Kamar, Iriepa Isabel, Diez‐Iriepa Daniel, Marco‐Contelles José, Ismaili Lhassane, Chabchoub Fakher: Synthesis of (±)‐cis‐1‐Aryl‐3‐oxo‐2,3‐dihydro‐1H‐benzo[f]chromene‐2‐carbonitriles and (±)‐trans‐4‐Aryl‐2‐oxo‐3,4‐dihydro‐2H‐benzo[h]chromene‐3‐carbonitriles. ChemistrySelect 2019, 4, 12902. <https://doi.org/10.1002/slct.201903982>
  • Rosati Ornelio, Lanari Daniela, Scavo Raffaella, Persia Diana, Marmottini Fabio, Nocchetti Morena, Curini Massimo, Piermatti Oriana: Zirconium potassium phosphate methyl and/or phenyl phosphonates as heterogeneous catalysts for Knoevenagel condensation under solvent free conditions. Microporous and Mesoporous Materials 2018, 268, 251. <https://doi.org/10.1016/j.micromeso.2018.04.035>
  • Khazaei Ardeshir, Bashirian Ehsan, Ranjbaran Azam, Khazaei Marzieh, Moosavi‐Zare Ahmad Reza: The Synthesis of 2,11‐Diamino‐4,9‐diphenyl‐4,9‐dihydrobenzo [f] pyrano[3,2‐h]chromene‐3,10‐dicarbonitrile Derivatives using Triethanolammonium Acetate as a Green Ionic Liquid. J Chinese Chemical Soc 2017, 64, 757. <https://doi.org/10.1002/jccs.201700019>
  • Salama Soad K., Darweesh Ahmed F., Abdelhamid Ismail A., Elwahy Ahmed H. M.: Microwave Assisted Green Multicomponent Synthesis of Novel bis(2‐Amino‐tetrahydro‐4H‐chromene‐3‐carbonitrile) Derivatives Using Chitosan as Eco‐friendly Basic Catalyst. Journal of Heterocyclic Chem 2017, 54, 305. <https://doi.org/10.1002/jhet.2584>
  • Mohamed Hany M., Fouda Ahmed M., Khattab Essam S.A.E.H., Agrody Ahmed M. El-, Afifi Tarek H.: Synthesis, in-vitro cytotoxicity of 1H-benzo[f]chromene derivatives and structure–activity relationships of the 1-aryl group and 9-position. Zeitschrift für Naturforschung C 2017, 72, 161. <https://doi.org/10.1515/znc-2016-0139>
  • Elinson Michail N., Ryzhkov Fedor V., Nasybullin Ruslan F., Vereshchagin Anatoly N., Egorov Mikhail P.: Fast Efficient and General PASE Approach to Medicinally Relevant 4H,5H‐Pyrano‐[4,3‐b]pyran‐5‐one and 4,6‐Dihydro‐5H‐pyrano‐[3,2‐c]pyridine‐5‐one Scaffolds. Helvetica Chimica Acta 2016, 99, 724. <https://doi.org/10.1002/hlca.201600150>
  • Badrey Mohamed Gomaa, Gomha Sobhi Mohamed, Mashaly Hamada Moustafa: Synthesis and studies on chromene based reactive azo dyes and their applications on different fabrics. Eur. J. Chem. 2016, 7, 146. <https://doi.org/10.5155/eurjchem.7.2.146-151.1393>
  • Samadi Abdelouahid, Silva Daniel, Chioua Mourad, Infantes Lourdes, Soriano Elena, Marco-Contelles José: The reaction of 2-amino-4 $$H$$ H -pyrans with $$N$$ N -bromosuccinimide. Mol Divers 2015, 19, 103. <https://doi.org/10.1007/s11030-014-9560-4>
  • Adili Alafate, Tao Zhong-Lin, Chen Dian-Feng, Han Zhi-Yong: Quinine-catalyzed highly enantioselective cycloannulation of o-quinone methides with malononitrile. Org. Biomol. Chem. 2015, 13, 2247. <https://doi.org/10.1039/C4OB02602K>
  • Mohamed Shaaban K., Horton Peter N., Akkurt Mehmet, Younes Sabry H. H., Albayati Mustafa R.: Crystal structure of 2-amino-4-phenyl-4H-benzo[h]chromene-3-carbonitrile. Acta Crystallogr E Cryst Commun 2015, 71, o516. <https://doi.org/10.1107/S2056989015011536>
  • Behbahani Farahnaz K., Mehraban Sima: Synthesis of 2-Amino-3-cyano-7-hydroxy-4H-chromenes Using L-Proline as a Biocatalyst. Journal of the Korean Chemical Society 2015, 59, 284. <https://doi.org/10.5012/jkcs.2015.59.4.284>
  • Shinde Shital, Rashinkar Gajanan, Salunkhe Rajashri: DABCO entrapped in agar-agar: A heterogeneous gelly catalyst for multi-component synthesis of 2-amino-4H-chromenes. Journal of Molecular Liquids 2013, 178, 122. <https://doi.org/10.1016/j.molliq.2012.10.019>
  • Elinson M. N., Nasybullin R. F., Nikishin G. I.: Electrocatalytic Fast and Efficient Multicomponent Approach to Medicinally Relevant Pyrano[3,2-c]quinolone Scaffold. J. Electrochem. Soc. 2013, 160, G3053. <https://doi.org/10.1149/2.009307jes>
  • Khalil Khaled, Al-Matar Hamad: Chitosan Based Heterogeneous Catalyses: Chitosan-Grafted-Poly(4-Vinylpyridne) as an Efficient Catalyst for Michael Additions and Alkylpyridazinyl Carbonitrile Oxidation. Molecules 2013, 18, 5288. <https://doi.org/10.3390/molecules18055288>
  • Verma Sanny, Jain Suman L.: Thiourea dioxide catalyzed multi-component coupling reaction for the one step synthesis of naphthopyran derivatives. Tetrahedron Letters 2012, 53, 6055. <https://doi.org/10.1016/j.tetlet.2012.08.118>
  • Maalej Emna, Chabchoub Fakher, Samadi Abdelouahid, de los Ríos Cristóbal, Perona Almudena, Morreale Antonio, Marco-Contelles José: Synthesis, biological assessment and molecular modeling of 14-aryl-10,11,12,14-tetrahydro-9H-benzo[5,6]chromeno[2,3-b]quinolin-13-amines. Biorg Med Chem Lett 2011, 21, 2384. <https://doi.org/10.1016/j.bmcl.2011.02.094>
  • Mohtat Bita, Djahaniani Hoorieh, Yavari Issa, Dehbalaei Masomeh G., Jam Saba A.: Synthesis of 4H-chromene derivatives by reaction between alkyl isocyanides and dialkyl acetylenedicarboxylate in the presence of 6-hydroxyquinoline. Chin Chem Lett 2011, 22, 771. <https://doi.org/10.1016/j.cclet.2011.01.005>
  • Ding Derong, Zhao Cong-Gui: Organocatalyzed synthesis of 2-amino-8-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitriles. Tetrahetron Lett 2010, 51, 1322. <https://doi.org/10.1016/j.tetlet.2009.12.139>
  • Wang Xiao-Sheng, Yang Gao-Sheng, Zhao Gang: Enantioselective synthesis of naphthopyran derivatives catalyzed by bifunctional thiourea-tertiary amines. Tet Asymm 2008, 19, 709. <https://doi.org/10.1016/j.tetasy.2008.02.018>
  • Balalaie Saeed, Ramezanpour Sorour, Bararjanian Morteza, Gross Jürgen H.: DABCO‐Catalyzed Efficient Synthesis of Naphthopyran Derivatives via One‐Pot Three‐Component Condensation Reaction at Room Temperature. Synthetic Communications 2008, 38, 1078. <https://doi.org/10.1080/00397910701862865>
  • Velikorodov A. V., Imasheva N. M.: Synthesis of carbamate derivatives of coumarin and chromene. Russ J Org Chem 2008, 44, 1374. <https://doi.org/10.1134/S1070428008090212>
  • Patra Amarendra, Mahapatra Tanusri: Aliquat 336 Catalysed Three-Component Condensation in an Aqueous Media: A Synthesis of 1H- and 4H-benzochromenes. Journal of Chemical Research 2008, 2008, 405. <https://doi.org/10.3184/030823408785702490>
  • Magedov Igor V., Manpadi Madhuri, Evdokimov Nikolai M., Elias Eerik M., Rozhkova Elena, Ogasawara Marcia A., Bettale Jennifer D., Przheval’skii Nikolai M., Rogelj Snezna, Kornienko Alexander: Antiproliferative and apoptosis inducing properties of pyrano[3,2-c]pyridones accessible by a one-step multicomponent synthesis. Biorg Med Chem Lett 2007, 17, 3872. <https://doi.org/10.1016/j.bmcl.2007.05.004>
  • Kumar B. Sunil, Srinivasulu N., Udupi R. H., Rajitha B., Reddy Y. Thirupathi, Reddy P. Narsimha, Kumar P. S.: An efficient approach towards three component coupling of one pot reaction for synthesis of functionalized benzopyrans. Journal of Heterocyclic Chem 2006, 43, 1691. <https://doi.org/10.1002/jhet.5570430641>
  • Jin Tong‐Shou, Zhang Jian‐She, Liu Li‐Bin, Wang Ai‐Qing, Li Tong‐Shuang: Clean, One‐Pot Synthesis of Naphthopyran Derivatives in Aqueous Media. Synthetic Communications 2006, 36, 2009. <https://doi.org/10.1080/00397910600632096>
  • Wen Xin-Min, Wang Hui-Yun, Li Shu-Ling: Aqueous [bmim][BF4] as Green Solvent in Microwave-assisted Organic Reactions: Clean Synthesis of 1H-benzo[f]chromene Derivatives. Journal of Chemical Research 2006, 2006, 776. <https://doi.org/10.3184/030823406780199767>
  • Messaád, Mehadi, Chabchoub, Fakher, Salem, Mansour: ACTION OF PRIMARY AMINES AND HYDROXYLAMINE ON ETHOXYMETHYLENEAMINONAPHTOPYRANES: SYNTHESIS OF NEW NAPHTOPYRANO [2,3-d] PYRIMIDINES DERIVATIVES. HC 2005, 11, 139. <https://doi.org/10.1515/HC.2005.11.2.139>
  • Maggi Raimondo, Ballini Roberto, Sartori Giovanni, Sartorio Raffaella: Basic alumina catalysed synthesis of substituted 2-amino-2-chromenes via three-component reaction. Tetrahetron Lett 2004, 45, 2297. <https://doi.org/10.1016/j.tetlet.2004.01.115>
  • Wang Xiang‐shan, Shi Da‐qing, Yu Hui‐zhen, Wang Gao‐feng, Tu Shu‐jiang: Synthesis of 2‐Aminochromene Derivatives Catalyzed by KF/Al2O3. Synthetic Communications 2004, 34, 509. <https://doi.org/10.1081/SCC-120027291>
  • Wang Xiang‐Shan, Shi Da‐Qing, Tu Shu‐Jiang: Synthesis of 2‐aminochromene derivatives catalyzed by KF/Al2O3. Chin. J. Chem. 2003, 21, 1114. <https://doi.org/10.1002/cjoc.20030210903>
  • Yavari Issa, Djahaniani Hoorieh, Nasiri Farough: Reaction between alkyl isocyanides and dimethyl acetylenedicarboxylate in the presence of polyhydroxybenzenes. Synthesis of 4H-chromene derivatives. Tetrahedron 2003, 59, 9409. <https://doi.org/10.1016/j.tet.2003.09.072>
  • Yavari Issa, Anary-Abbasinejad Mohammad, Alizadeh Abdolali, Hossaini Zinatossadat: A simple and efficient approach to the synthesis of highly functionalized fused benzochromenes. Tetrahedron 2003, 59, 1289. <https://doi.org/10.1016/S0040-4020(03)00030-9>
  • Ballini Roberto, Bosica Giovanna, Conforti Maria Lina, Maggi Raimondo, Mazzacani Alessandro, Righi Paolo, Sartori Giovanni: Three-component process for the synthesis of 2-amino-2-chromenes in aqueous media. Tetrahedron 2001, 57, 1395. <https://doi.org/10.1016/S0040-4020(00)01121-2>
  • Sayed Ahmed Z., El-Hady Nagwa A., El-Agrody Ahmed M.: Condensation of α-cyanocinnamonitriles with 6-bromo-2-naphthol: Synthesis of pyrano [2,3-d]pyrimidine and pyrano[3,2-e] [1,2,4]triazolo[2,3-c]pyrimidine derivatives. Journal of Chemical Research 2000, 2000, 164. <https://doi.org/10.3184/030823400103167002>
  • Al-Mousawi Saleh M., Elkholy Yehia M., Mohammad Mohammad A., Elnagdi Mohammad H.: SYNTHESIS OF NEW CONDENSED 2-AMINO-4H-PYRAN-3-CARBONITRILES AND OF 2-AMINOQUINOLINE-3-CARBONITRILES. Org Prep Proced Int 1999, 31, 305. <https://doi.org/10.1080/00304949909458324>
  • Sharanin Yu A, Goncharenko M P, Litvinov Victor P: Reactions of carbonyl compounds with α,β-unsaturated nitriles as a convenient pathway to carbo- and heterocycles. Russ. Chem. Rev. 1998, 67, 393. <https://doi.org/10.1070/RC1998v067n05ABEH000371>
  • Al-Omran Fatima, El-Ghamry Ibrahim, Elnagdi Mohammed H.: NEW SPIROPYRAN-4-YLINDOLIDINE DERIVATIVES FROM THE REACTION OF 2-OXO-3-CYANOMETHYLIDENE-2,3-DIHYDROINDOLES WITH CYCLOHEXANEDIONES AND PHENOLS. Org Prep Proced Int 1998, 30, 363. <https://doi.org/10.1080/00304949809355299>
  • Erian Ayman Wahba, Elkholy Yehya Mahmoud, Al-arab Elham Ezz, Elnagdf Mohamed Hilmy: POLYFUNCTIONALLY SUBSTITUTED HETEROCYCLES: SYNTHESIS OF NEW POLYFUNCTIONALLY SUBSTITUTED PHTHALAZINES, PYRIDO[3,4-C]PYRIDAZINES AND PYRAZOLO[3,4-C]PYRIDAZINES. Phosphorus, Sulfur, and Silicon and the Related Elements 1997, 122, 133. <https://doi.org/10.1080/10426509708043501>
  • Martín Nazario, Martínez‐Grau Angeles, Seoane Carlos, Marco José L., Albert Armando, Cano Félix H.: First asymmetric synthesis of 3‐alkoxycarbonyl‐2‐amino‐4‐aryl‐4H‐naphtho[1,2‐b]pyrans. Journal of Heterocyclic Chem 1996, 33, 27. <https://doi.org/10.1002/jhet.5570330105>
  • Martín Nazario, Martínez‐Grau Angeles, Seoane Carlos, Marco José L.: The synthesis of 2‐amino‐4‐aryl‐3‐ethoxycarbonyl‐4H‐naphtho[1,2‐b]pyrans revisited. Journal of Heterocyclic Chem 1995, 32, 1225. <https://doi.org/10.1002/jhet.5570320422>
  • Smith Colin W., Bailey James M., Billingham Michael E.J., Chandrasekhar Srinivasan, Dell Colin P., Harvey Anita K., Hicks Caroline A., Kingston Ann E., Wishart Graham N.: The anti-rheumatic potential of a series of 2,4-di-substituted-4H-naphtho[1,2-b]pyran-3-carbonitriles. Biorg Med Chem Lett 1995, 5, 2783. <https://doi.org/10.1016/0960-894X(95)00487-E>
  • Elagamey Abdel Ghani Ali, El-Taweel Fathy Mohamed Abdel-Aziz, Khodeir Mohamed Nabil Mohamed, Elnagdi Mohamed Hilmy: Nitriles in Heterocyclic Synthesis. The Reaction of Polyhydric Naphthalenes, 4-Methylcoumarin-3-carbonitrile, and Alkylidenemalononitrile with Methylenemalononitrile. Bulletin of the Chemical Society of Japan 1993, 66, 464. <https://doi.org/10.1246/bcsj.66.464>
  • Hafez Ali A. Abdel, Awad Ibrahim M. A., Monem Maisa I. Abdel: Nitriles in heterocyclic synthesis. Part III: New sulpha drugs related to cyanopyridine derivatives. J of Chemical Tech & Biotech 1992, 55, 333. <https://doi.org/10.1002/jctb.280550405>
  • ELAGAMEY A. G. A., SAWLLIM S. Z., EL‐TAWEEL F. M. A., ELNAGDI M. H.: ChemInform Abstract: Nitriles in Heterocyclic Synthesis: Novel Syntheses of Benzo(b)pyrans, Naphtho(1,2‐b)pyrans, Naphtho(2,1‐b)pyrans, Pyrano(3,2‐h)quinolines and Pyrano(3,2‐c)quinolines. ChemInform 1988, 19. <https://doi.org/10.1002/chin.198846084>