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First synthesis of 2-(2,4,4-trimethyl-3,4-dihydro-2H-benzo[h]chromen-2-yl)-1-naphthol and 3-(2,4,4-trimethyl-3,4-dihydro-2H-benzo[g]chromen-2-yl)-2-naphthol from 1- and 2-naphthol derivatives

✍ Scribed by Jose C. J. M. D. S. Menezes; Bikshandarkoil R. Srinivasan; Pallepogu Raghavaiah; Shashikumar K. Paknikar; Shrivallabh P. Kamat

Publisher: Journal of Heterocyclic Chemistry
Year: 2010
Tongue: English
Weight: 302 KB
Volume: 48
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.473

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✦ Synopsis

Abstract

Two new structurally isomeric, 2‐(2,4,4‐trimethyl‐3,4‐dihydro‐2__H__‐benzo[h]chromen‐2‐yl)‐1‐naphthol (1**)** and 3‐(2,4,4‐trimethyl‐3,4‐dihydro‐2__H__‐benzo[g]chromen‐2‐yl)‐2‐naphthol (3) have been synthesized from 2‐acetyl‐1‐naphthol and ethyl‐3‐hydroxy‐2‐naphthoate, respectively, involving Grignard reaction, dehydration of the corresponding tertiary alcohols, and hetero Diels–Alder dimerization. The two benzochromenes (1 and 3) have been fully characterized by IR, NMR, and HRESIMS data. Their structures are further supported by crystallography of their corresponding acetates (2 and 4). J. Heterocyclic Chem., (2011).

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