Molecules 2012, 17(10), 12225-12233; doi:10.3390/molecules171012225
Article

Studies on 2-Arylhydrazononitriles: Synthesis of 3-Aryl-2-arylhydrazopropanenitriles and Their Utility as Precursors to 2-Substituted Indoles, 2-Substituted-1,2,3-Triazoles, and 1-Substituted Pyrazolo[4,3-d]pyrimidines

Khaled D. Khalil 1,2,* email and Hamad M. Al-Matar 1 email
1 Chemistry Department, Faculty of Science, University of Kuwait, P.O. Box 5969, Safat 13060, Kuwait 2 Chemistry Department, Faculty of Science, Cairo University, Giza, 12613, Egypt
* Author to whom correspondence should be addressed.
Received: 27 August 2012; in revised form: 23 September 2012 / Accepted: 26 September 2012 / Published: 18 October 2012
(This article belongs to the Section Organic Synthesis)
PDF Full-text Download PDF Full-Text [190 KB, Updated Version, uploaded 23 October 2012 13:59 CEST]
The original version is still available [190 KB, uploaded 18 October 2012 11:37 CEST]
Abstract: Coupling of 2-benzylmalononitrile with aromatic diazonium salts afforded 3-phenyl-2-arylhydrazonopropanenitriles 4a,b, which were rearranged into 2-cyanoindoles 5a,b upon heating with ZnCl2 in the presence of glacial acetic acid. The produced indole derivatives 5a,b can be successfully used as valuable precursors to synthesize 1,2,4-oxadiazolylindoles 8a,b. The reaction of arylhydrazononitriles 4a,b with hydroxylamine afforded an amidoximes 9a,b that could be cyclized into 1,2,3-triazole-4-amines 10a,b. In addition, 4a,b could be converted into 4-aminopyrazoles 12a,b via condensation with chloroacetonitrile in the presence of triethylamine as a basic catalyst. Finally, compounds 12a,b were refluxed with dimethylformamide dimethylacetal (DMFDMA) to afford amidines 13a,b that were readily cyclized to the corresponding pyrazolo[4,3-d]pyrimidines 14a,b when refluxed with ammonium acetate.
Keywords: benzylidenemalononitrile; 2-arylhydrazononitrile; amidoxime; cyanoindole; dimethylformamide dimethylacetal; 1,2,3-triazole

Article Statistics

Click here to load and display the download statistics.

Cite This Article

MDPI and ACS Style

Khalil, K.D.; Al-Matar, H.M. Studies on 2-Arylhydrazononitriles: Synthesis of 3-Aryl-2-arylhydrazopropanenitriles and Their Utility as Precursors to 2-Substituted Indoles, 2-Substituted-1,2,3-Triazoles, and 1-Substituted Pyrazolo[4,3-d]pyrimidines. Molecules 2012, 17, 12225-12233.

AMA Style

Khalil KD, Al-Matar HM. Studies on 2-Arylhydrazononitriles: Synthesis of 3-Aryl-2-arylhydrazopropanenitriles and Their Utility as Precursors to 2-Substituted Indoles, 2-Substituted-1,2,3-Triazoles, and 1-Substituted Pyrazolo[4,3-d]pyrimidines. Molecules. 2012; 17(10):12225-12233.

Chicago/Turabian Style

Khalil, Khaled D.; Al-Matar, Hamad M. 2012. "Studies on 2-Arylhydrazononitriles: Synthesis of 3-Aryl-2-arylhydrazopropanenitriles and Their Utility as Precursors to 2-Substituted Indoles, 2-Substituted-1,2,3-Triazoles, and 1-Substituted Pyrazolo[4,3-d]pyrimidines." Molecules 17, no. 10: 12225-12233.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert