Abnormal Fischer indolization and its related compounds. XXII. Fischer indolization of ethyl pyruvate 2-(2-chloro- and 2,6-dichlorophenyl)methylhydrazones.
Тип публикации: Journal Article
Дата публикации: 2011-12-08
scimago Q3
wos Q3
БС2
SJR: 0.349
CiteScore: 2.7
Impact factor: 1.3
ISSN: 00092363, 13475223
General Chemistry
Drug Discovery
General Medicine
Краткое описание
The Fischer indolization of ethyl pyruvate 2-(2-chlorophenyl)methylhydrazone (17) with HCl/EtOH proceeded rapidly to give six 1-methylindoles, ethyl 7-chloro (19), 6-chloro (22), and unsubstituted (24)-1-methylindole-2-car-boxylates, and dichloro derivatives (21, 23, and 26), whereas no indolization had occurred with the correspinding NH-hydrazone, as described in a previous paper. This result shows that the abnormal Fischer indolization of 2-chloro-phenylhydrazones with HCl/EtOH occurred in an ortho-C6 fashion, in the same manner as that of the corresponding 2-methoxyphenylhydrazones (1 and 2).The Fischer indolization of ethyl pyruvate 2-(2, 6-dichlorophenyl)methylhydrazone (18) with HCl/EtOH did not occur at all, whereas the reaction with ZnCl2/AcOH gave a low yield of ethyl 5, 7-dichloro-3-methylindole-2-carboxylate (36), which was formed by migration of the N-methyl group during Fischer indolization.
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Ishii H., Murakami Y., Ishikawa T. Abnormal Fischer indolization and its related compounds. XXII. Fischer indolization of ethyl pyruvate 2-(2-chloro- and 2,6-dichlorophenyl)methylhydrazones. // Chemical and Pharmaceutical Bulletin. 2011. Vol. 38. No. 3. pp. 597-604.
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Ishii H., Murakami Y., Ishikawa T. Abnormal Fischer indolization and its related compounds. XXII. Fischer indolization of ethyl pyruvate 2-(2-chloro- and 2,6-dichlorophenyl)methylhydrazones. // Chemical and Pharmaceutical Bulletin. 2011. Vol. 38. No. 3. pp. 597-604.
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TY - JOUR
DO - 10.1248/cpb.38.597
UR - https://doi.org/10.1248/cpb.38.597
TI - Abnormal Fischer indolization and its related compounds. XXII. Fischer indolization of ethyl pyruvate 2-(2-chloro- and 2,6-dichlorophenyl)methylhydrazones.
T2 - Chemical and Pharmaceutical Bulletin
AU - Ishii, Hisashi
AU - Murakami, Yasuoki
AU - Ishikawa, Tsutomu
PY - 2011
DA - 2011/12/08
PB - Pharmaceutical Society of Japan
SP - 597-604
IS - 3
VL - 38
SN - 0009-2363
SN - 1347-5223
ER -
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@article{2011_Ishii,
author = {Hisashi Ishii and Yasuoki Murakami and Tsutomu Ishikawa},
title = {Abnormal Fischer indolization and its related compounds. XXII. Fischer indolization of ethyl pyruvate 2-(2-chloro- and 2,6-dichlorophenyl)methylhydrazones.},
journal = {Chemical and Pharmaceutical Bulletin},
year = {2011},
volume = {38},
publisher = {Pharmaceutical Society of Japan},
month = {dec},
url = {https://doi.org/10.1248/cpb.38.597},
number = {3},
pages = {597--604},
doi = {10.1248/cpb.38.597}
}
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Ishii, Hisashi, et al. “Abnormal Fischer indolization and its related compounds. XXII. Fischer indolization of ethyl pyruvate 2-(2-chloro- and 2,6-dichlorophenyl)methylhydrazones..” Chemical and Pharmaceutical Bulletin, vol. 38, no. 3, Dec. 2011, pp. 597-604. https://doi.org/10.1248/cpb.38.597.