Azolyacetones as Precursors to Indoles and Naphthofurans Facilitated by Microwave Irradiation with Simultaneous Cooling

doi:10.3390/molecules14082976

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Molecules 2009, 14(8), 2976-2984; doi:10.3390/molecules14082976

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Azolyacetones as Precursors to Indoles and Naphthofurans Facilitated by Microwave Irradiation with Simultaneous Cooling

Saleh Mohammed Al-Mousawi* and Morsy Ahmed El-Apasery

Department of Chemistry, Faculty of Science; University of Kuwait, Safat, 13060, P.O. Box 12613, Kuwait

* Author to whom correspondence should be addressed.

Received: 8 July 2009; in revised form: 30 July 2009 / Accepted: 5 August 2009 / Published: 11 August 2009

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Abstract: Phthalimide reacted with phenacyl bromide under microwave irradiation to yield phenacyl isoindolidene-1,3-dione (3b), while 3a reacted with phenylhydrazine to yield the phenylhydrazone 4 that was readily converted into indoylphthalimide 8. Similarly N-benzotriazolylacetone (6a) reacted with phenyl hydrazine to yield the phenylhydrazone 7a that was converted into indoylbenzotriazole 9. Treatment of 8 with hydrazine hydrate afforded a mixture of phthalhydrazide 10 and 3-amino-2-methylindole (11). Reacting enaminone 13 with naphthoquinone (14) afforded the aryl naphthofuran 17. The possibility of the formation of the aldehyde 18 was excluded based on HMQC, which revealed that the carbonyl carbon is not linked to any hydrogen.

Keywords: microwave irradiation; aminoindole; naphthofuran; azolylacetone

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Correction
A correction was published on 28 December 2009: http://www.mdpi.com/1420-3049/15/1/93 (PDF, 19 KB)

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MDPI and ACS Style

Al-Mousawi, S.M.; El-Apasery, M.A. Azolyacetones as Precursors to Indoles and Naphthofurans Facilitated by Microwave Irradiation with Simultaneous Cooling. Molecules 2009, 14, 2976-2984.

AMA Style

Al-Mousawi SM, El-Apasery MA. Azolyacetones as Precursors to Indoles and Naphthofurans Facilitated by Microwave Irradiation with Simultaneous Cooling. Molecules. 2009; 14(8):2976-2984.

Chicago/Turabian Style

Al-Mousawi, Saleh M.; El-Apasery, Morsy A. 2009. "Azolyacetones as Precursors to Indoles and Naphthofurans Facilitated by Microwave Irradiation with Simultaneous Cooling." Molecules 14, no. 8: 2976-2984.

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