TY - JOUR
T1 - Site-Selective Conversion of Azido Groups at Carbonyl α-Positions to Diazo Groups in Diazido and Triazido Compounds
AU - Yokoi, Taiki
AU - Tanimoto, Hiroki
AU - Ueda, Tomomi
AU - Morimoto, Tsumoru
AU - Kakiuchi, Kiyomi
N1 - Publisher Copyright:
© 2018 American Chemical Society.
PY - 2018/10/5
Y1 - 2018/10/5
N2 - This paper reports on the selective conversion of alkyl azido groups at the carbonyl α-position to diazo compounds. Through β-elimination of dinitrogen, followed by hydrazone formation/decomposition, α-azidocarbonyl moieties were transformed into α-diazo carbonyl groups in one step. As these reaction conditions do not involve aryl or general alkyl azides, site-selective conversions of di- and triazides were achieved. Through this method, the successive site-selective conjugation of the triazido molecule with three different components is demonstrated.
AB - This paper reports on the selective conversion of alkyl azido groups at the carbonyl α-position to diazo compounds. Through β-elimination of dinitrogen, followed by hydrazone formation/decomposition, α-azidocarbonyl moieties were transformed into α-diazo carbonyl groups in one step. As these reaction conditions do not involve aryl or general alkyl azides, site-selective conversions of di- and triazides were achieved. Through this method, the successive site-selective conjugation of the triazido molecule with three different components is demonstrated.
UR - http://www.scopus.com/inward/record.url?scp=85054266371&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.8b02074
DO - 10.1021/acs.joc.8b02074
M3 - 学術論文
C2 - 30260220
AN - SCOPUS:85054266371
SN - 0022-3263
VL - 83
SP - 12103
EP - 12121
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -