Unexpected formation of dinaphtho[2,1-b:1’,2’-d]pyran

ORGN 387

Harish K. Cherivirala and G L David Gazula. Department of Chemistry, Osmania University, University of Scinece, Hyderabad, Andhra Pradesh, 500 007, India
1,1’-Bi-2-naphthol gained significant importance as synthon to construct fused oxygen containing heterocyclic systems. However, it is reported that attempts to synthesize fused cyclic ethers like bisnaphthopyrans from this synthetic precursor was unsuccessful by usual synthetic methods. Herein, we reporting the formation of dinaphtho[2,1-b:1’,2’-d]pyran (3) starting from 1,1’-bi-2-naphthol (1) by an unexpected synthetic pathway. Reaction of 1,1’-bi-2-naphthol with 2-propynyl bromide in acetone - potassium carbonate gave 2,2’-bis(2-propynyloxy)-1,1’-binaphthyl (2) which on refluxing in N,N-diethyl aniline afforded the title compound in quantitative yields.

 

Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster

Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003