European Journal of Chemistry 2014, 5(2), 277-286 | doi: https://doi.org/10.5155/eurjchem.5.2.277-286.976 | Get rights and content






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Friedel-Crafts chemistry: Part 41. A new facile synthesis of indeno[1,2-c] pyrazoles, 2H-benzo[g]indazoles and benzo[6,7]cyclohepta[1,2-c]pyrazoles via Friedel-Crafts ring closures


Hassan Abdou Kotb Abd El-Aal (1,*) , Ahmed Mahmoud Abdel Mageed El-Khawaga (2) , Ali Ali Khalaf (3)

(1) Chemistry Department, Faculty of Science, Assiut University, Assiut, 71516, Egypt
(2) Chemistry Department, Faculty of Science, Assiut University, Assiut, 71516, Egypt
(3) Chemistry Department, Faculty of Science, Assiut University, Assiut, 71516, Egypt
(*) Corresponding Author

Received: 17 Nov 2013 | Revised: 25 Dec 2013 | Accepted: 01 Jan 2014 | Published: 30 Jun 2014 | Issue Date: June 2014

Abstract


Expedient and novel alternative synthesis of some fused heteropolycycles containing pyrazole moiety is described. A series of indeno[1,2-c]pyrazoles, 2H-benzo[g]indazoles and benzo[6,7] cyclohepta[1,2-c]pyrazoles were prepared by Friedel-Crafts ring closure of suitable synthesized carboxylic acids and alkanols in the presence of AlCl3/CH3NO2 or P2O5 or PPA (polyphosphoric acid) catalysts. The precursor acids were obtained by utilizing KMnO4 oxidation of the corresponding aldehyde, alkylations of diethyl malonates and Perkin type approaches, whereas starting alkanols were smoothly obtained by reaction of carboxylic acid ester with Grignard reagent. To exemplify, cyclizations of 5-chloro-1,3-diphenyl-1H-pyrazole-4-carboxylic acid (6) were accomplished using the above catalysts afforded 3-chloro-2-phenylindeno[1,2-c]pyrazol-4(2H)-one (1b). Similarly, cyclization of the 2-(5-chloro-1,3-diphenyl-1H-pyrazol-4-yl)propan-2-ol (8) by a Friedel–Crafts-type ring closure afforded the 3-chloro-2,4-dihydro-4,4-dimethyl-2-phenylindeno[1,2-c]pyrazole (1a).


Keywords


Benzo[g]indazole; Heteropolycycles; Heteroarylalkanols; Indeno[1,2-c]pyrazole; Friedel-Crafts ring closures; Benzo[6,7]cyclohepta[1,2-c]pyrazole

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DOI: 10.5155/eurjchem.5.2.277-286.976

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Chemistry Department, Faculty of Science, Assiut University, Assiut, Egypt

Citations

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[1]. Qingrui Li, Yunnian Yin, Yabo Li, Jianye Zhang, Mengmeng Huang, Jung Keun Kim, Yangjie Wu
A simple approach to indeno-coumarins via visible-light-induced cyclization of aryl alkynoates with diethyl bromomalonate
Organic Chemistry Frontiers  6(18), 3238, 2019
DOI: 10.1039/C9QO00795D
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[2]. Hassan A. K. Abd El-Aal, Ali A. Khalaf
Friedel–Crafts Chemistry. Part 46. Unprecedented Construction of Tricyclic Pyrazolo[3,4-b]quinolines, -[1,8]naphthyridines, -azepines, -azocines, -pyrido[3,2-g]azocines, and pyrazolo[3,4-b]azonines via Friedel–Crafts Ring Closures
Australian Journal of Chemistry  69(6), 652, 2016
DOI: 10.1071/CH15526
/


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How to cite


Abd El-Aal, H.; El-Khawaga, A.; Khalaf, A. Eur. J. Chem. 2014, 5(2), 277-286. doi:10.5155/eurjchem.5.2.277-286.976
Abd El-Aal, H.; El-Khawaga, A.; Khalaf, A. Friedel-Crafts chemistry: Part 41. A new facile synthesis of indeno[1,2-c] pyrazoles, 2H-benzo[g]indazoles and benzo[6,7]cyclohepta[1,2-c]pyrazoles via Friedel-Crafts ring closures. Eur. J. Chem. 2014, 5(2), 277-286. doi:10.5155/eurjchem.5.2.277-286.976
Abd El-Aal, H., El-Khawaga, A., & Khalaf, A. (2014). Friedel-Crafts chemistry: Part 41. A new facile synthesis of indeno[1,2-c] pyrazoles, 2H-benzo[g]indazoles and benzo[6,7]cyclohepta[1,2-c]pyrazoles via Friedel-Crafts ring closures. European Journal of Chemistry, 5(2), 277-286. doi:10.5155/eurjchem.5.2.277-286.976
Abd El-Aal, Hassan, Ahmed Mahmoud Abdel Mageed El-Khawaga, & Ali Ali Khalaf. "Friedel-Crafts chemistry: Part 41. A new facile synthesis of indeno[1,2-c] pyrazoles, 2H-benzo[g]indazoles and benzo[6,7]cyclohepta[1,2-c]pyrazoles via Friedel-Crafts ring closures." European Journal of Chemistry [Online], 5.2 (2014): 277-286. Web. 31 May. 2020
Abd El-Aal, Hassan, El-Khawaga, Ahmed, AND Khalaf, Ali. "Friedel-Crafts chemistry: Part 41. A new facile synthesis of indeno[1,2-c] pyrazoles, 2H-benzo[g]indazoles and benzo[6,7]cyclohepta[1,2-c]pyrazoles via Friedel-Crafts ring closures" European Journal of Chemistry [Online], Volume 5 Number 2 (30 June 2014)

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