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One‐Pot Synthesis of 3‐Substituted 3,4‐Dihydro‐1,2,3‐benzotriazine Derivatives Based on the Reaction of o ‐Bromobenzyl Azides with Butyllithium
Author(s) -
Kobayashi Kazuhiro,
Chikazawa Yuuki
Publication year - 2016
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201500234
Subject(s) - chemistry , lithium (medication) , intramolecular force , butyllithium , reaction conditions , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , medicine , endocrinology
An efficient one‐pot procedure for the preparation of 3‐substituted 3,4‐dihydro‐1,2,3‐benzotriazines 2, 3 , and 4 from o ‐bromobenzyl azides 1 is described. The reaction of these azides with BuLi in THF at −78° generates o ‐lithiobenzyl azides via the Br/Li exchange. These lithium compounds immediately undergo intramolecular cyclization to give the corresponding (dihydro‐1,2,3‐benzotriazinyl)lithium intermediates, which are trapped with a variety of acylating agents or BnBr at N(3) exclusively to provide the desired products in moderate to good yields.