Protecting groups for the pyrrole nitrogen atom. The 2-chloroethyl, 2-phenylsulfonylethyl, and related moieties
Тип публикации: Journal Article
Дата публикации: 1983-08-01
scimago Q3
wos Q4
БС3
SJR: 0.254
CiteScore: 2
Impact factor: 1
ISSN: 00084042, 14803291
General Chemistry
Catalysis
Organic Chemistry
Краткое описание
The 2-chloroethyl and 2-phenylsulfonylethyl moieties are versatile protecting groups for the pyrrole nitrogen atom. The 2-chloroethyl group is easily attached under phase transfer conditions using 1,2-dichloroethane. The 2-phenylsulfonylethyl moiety is readily appended under both phase transfer and homogeneous solution conditions using 2-phenylsulfonylcthyl chloride 5. Deprotection of the N-(2-chloroethyl)pyrroles is accomplished by means of efficient three-step, one-pot sequences via the N-vinyl compounds 3 and subsequent degradation of the N-(1-hydroxyethyl) compounds 4 or the acctoxymercuration derivatives 5 obtained therefrom. The 2-phenylsulfonylethyl group is excised by a reverse Michael reaction using sodium hydride or DBN as the base.The utility of the 2-chloroethyl protecting group is exemplified in a synthesis of benzyl cyclopenta[b] |pyrrole-5-carboxylate 13 from 1-(2-chloroethyl)-4-oxotetrahydroindolc 2d.
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González C. A. et al. Protecting groups for the pyrrole nitrogen atom. The 2-chloroethyl, 2-phenylsulfonylethyl, and related moieties // Canadian Journal of Chemistry. 1983. Vol. 61. No. 8. pp. 1697-1702.
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González C. A., Gonzalez C., Greenhouse R., Tallabs R., Muchowski J. M. Protecting groups for the pyrrole nitrogen atom. The 2-chloroethyl, 2-phenylsulfonylethyl, and related moieties // Canadian Journal of Chemistry. 1983. Vol. 61. No. 8. pp. 1697-1702.
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TY - JOUR
DO - 10.1139/v83-290
UR - https://doi.org/10.1139/v83-290
TI - Protecting groups for the pyrrole nitrogen atom. The 2-chloroethyl, 2-phenylsulfonylethyl, and related moieties
T2 - Canadian Journal of Chemistry
AU - González, C. A.
AU - Gonzalez, Carlos
AU - Greenhouse, Robert
AU - Tallabs, Ramon
AU - Muchowski, Joseph M.
PY - 1983
DA - 1983/08/01
PB - Canadian Science Publishing
SP - 1697-1702
IS - 8
VL - 61
SN - 0008-4042
SN - 1480-3291
ER -
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@article{1983_González,
author = {C. A. González and Carlos Gonzalez and Robert Greenhouse and Ramon Tallabs and Joseph M. Muchowski},
title = {Protecting groups for the pyrrole nitrogen atom. The 2-chloroethyl, 2-phenylsulfonylethyl, and related moieties},
journal = {Canadian Journal of Chemistry},
year = {1983},
volume = {61},
publisher = {Canadian Science Publishing},
month = {aug},
url = {https://doi.org/10.1139/v83-290},
number = {8},
pages = {1697--1702},
doi = {10.1139/v83-290}
}
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MLA
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González, C. A., et al. “Protecting groups for the pyrrole nitrogen atom. The 2-chloroethyl, 2-phenylsulfonylethyl, and related moieties.” Canadian Journal of Chemistry, vol. 61, no. 8, Aug. 1983, pp. 1697-1702. https://doi.org/10.1139/v83-290.