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Issue 14, 2014
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Microwave assisted base dependent regioselective synthesis of partially reduced chromenes, isochromenes and phenanthrenes

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Abstract

We have reported a microwave assisted base directed regioselective synthesis of partially reduced chromenes, isochromenes and phenanthrenes. Functionalized 4-(piperidin-1-yl)-5,6-dihydro-2H-benzo[h]-chromen-2-one-3-carbonitriles have been used as precursors, which on reaction with functionalized acetophenones in the presence of KOH in DMF under microwave irradiation yield (Z)-2-(2-aryl-5,6-dihydro-4H-benzo[f]isochromen-4-ylidene)acetonitriles. The use of NaH in DMF provides 3-aryl-1-(piperidin-1-yl)-9,10-dihydro phenanthrene-2-carbonitriles in excellent yield regioselectively. The use of cyclohexanone as a nucleophile source yields (Z)-2-(3,4,7,8-tetrahydro-1H-naphtho[2,1-c]chromen-6(2H)-ylidene)acetonitriles. The structure and geometry of isochromene have been proved without any ambiguity by single crystal X-ray diffraction.

Graphical abstract: Microwave assisted base dependent regioselective synthesis of partially reduced chromenes, isochromenes and phenanthrenes

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Publication details

The article was received on 27 Sep 2013, accepted on 04 Feb 2014 and first published on 04 Feb 2014


Article type: Paper
DOI: 10.1039/C3OB41962B
Citation: Org. Biomol. Chem., 2014,12, 2228-2234
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    Microwave assisted base dependent regioselective synthesis of partially reduced chromenes, isochromenes and phenanthrenes

    P. Yadav, S. Singh, S. N. Sahu, F. Hussain and R. Pratap, Org. Biomol. Chem., 2014, 12, 2228
    DOI: 10.1039/C3OB41962B

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