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First synthesis of 2‐(2,4,4‐trimethyl‐3,4‐dihydro‐2 H ‐benzo[ h ]chromen‐2‐yl)‐1‐naphthol and 3‐(2,4,4‐trimethyl‐3,4‐dihydro‐2 H ‐benzo[ g ]chromen‐2‐yl)‐2‐naphthol from 1‐ and 2‐naphthol derivatives
Author(s) -
Menezes Jose C. J. M. D. S.,
Srinivasan Bikshandarkoil R.,
Raghavaiah Pallepogu,
Paknikar Shashikumar K.,
Kamat Shrivallabh P.
Publication year - 2011
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.473
Subject(s) - chemistry , stereochemistry , dehydration , medicinal chemistry , biochemistry
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).