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Paper | Special issue | Vol 52, No. 3, 2000, pp.1133-1141
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S112
The Preparation of Certain Nitrogen and Sulfur Containing Polycyclic Heterocycles by the Reaction of Arynes Possessing Charged Groups with α-Lithio-α-cyano-o-tolunitrile and α-Lithio-3-thienylacetonitrile

Anlai Wang, Hongming Zhang, and Edward R. Biehl*

*Department of Chemistry, Southern Methodist University, P.O. Box 750314, Dallas, TX 75275, U.S.A.


The synthesis of a wide variety of polycyclic heterocycles by the reaction of arynes or hetarynes possessing charged substituents with lithiated 3-thiopheneacetonitrile (22) or α-cyano-o-tolunitrile (2) is reported. Specific heterocycles prepared include: 9-aminonaphtho[2,3-b]thiophen-8-yl]methanol from 2,3-dehydrobenzyl oxide and 22; 5-amino-4-hydroxybenzo[g]isoquinoline-10-carbonitrile from 3,4-dehydropyridine-oxide and 2; 4-aza-2-oxodibenzo[cd,g]indole-6-carbonitrile from 2,3-dehydronicotinamide and 2; and 5-methyl- and 5-methoxy-2-oxo-1,2-dihydrodibenzo[cd,g]indole-2-carbonitrile from 4-methyl- and 4-methoxy-benzyne-3-carboylate, respectively and 2. Possible mechanisms for these reactions are discussed.