A concise synthesis of 2-amino-1,2,3,4-tetrahydronaphthalene-6,7-diol ('6,7-ADTN') from naphthalene-2,3-diol
Özet
2-Amino-1,2,3,4-tetrahydronaphthalene-6,7-diol (2 6,7-ADTN) was synthesized starting from naphthalene-2.3-diol in seven steps and with an overall yield of 44%. Methylation of naphthalene-2.3-diol with dimethyl sulfate, followed by Friedel-Crafts acylation with AcCl, gave 2-acetyl-6,7-dimethoxynaphthalene. 2-Acetyl-6,7-dimethoxynaphthalene was converted to 6.7-dimethoxynaphthalene-2-carboxylic acid by a haloform reaction. Birch reduction of the carboxylic acid with 4 mol-equiv. of Na in liquid ammonia afforded 1,2,3,4-tetrahydro-6.7-dimethoxynaphthalene-2-carboxylic acid, from which 2 was obtained by a Curtius reaction, followed by hydrogenolysis and demethylation.
Atıf için künye
Göksu, S., Kazaz, C., SUTBEYAZ, Y., & Seçen, H. (2003). A concise synthesis of 2-amino-1,2,3,4-tetrahydronaphthalene-6,7-diol ('6,7-ADTN') from naphthalene-2,3-diol. HELVETICA CHIMICA ACTA, 86(10), 3310–3313. https://doi.org/10.1002/hlca.200390272
BibTeX
@article{goksu2003-70879,
author = {Göksu, Süleyman and Kazaz, Cavit and SUTBEYAZ, Yaşar and Seçen, Hasan},
title = {A concise synthesis of 2-amino-1,2,3,4-tetrahydronaphthalene-6,7-diol ('6,7-ADTN') from naphthalene-2,3-diol},
journal = {HELVETICA CHIMICA ACTA},
year = {2003},
volume = {86},
number = {10},
pages = {3310--3313},
issn = {0018-019X},
doi = {10.1002/hlca.200390272},
url = {https://akademik.atauni.edu.tr/yayinlar/70879-a-concise-synthesis-of-2-amino-1234-tetrahydronaphthalene-67-diol-67-adtn-from}
}