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One‐Pot Syntheses of 2‐ N ‐Alkylamino‐, 2‐ N ‐Phenylamino‐, 2‐ N, N ‐Dialkylamino‐, and 2‐ N ‐Alkyl‐ N ‐phenylaminothiophenes
Author(s) -
Tarasova Ol'ga A.,
Klyba Ludmila V.,
Vvedensky Vladimir Yu.,
Nedolya Nina A.,
Trofimov Boris A.,
Brandsma Lambert,
Verkruijsse Hermann D.
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199802)1998:2<253::aid-ejoc253>3.0.co;2-e
Subject(s) - chemistry , alkyl , medicinal chemistry , tetrahydrofuran , allene , adduct , phenyl isothiocyanate , isothiocyanate , alkyne , iodide , methyl iodide , organic chemistry , catalysis , solvent
A number of 2‐ N ‐alkylamino‐ or 2‐ N ‐phenylamino‐, 2‐ N, N ‐dialkylamino‐, and 2‐ N ‐alkyl‐ N ‐phenylaminothiophenes have been prepared in good yields by adding a solution of tert ‐butylalcohol and potassium tert ‐butoxide in dimethylsulfoxide to a solution of the adduct from a lithiated 1‐alkyne, RCH 2 C≡CLi, or the lithiated allene, t BuCH=C=CHLi, and isothiocyanate, R′N=C=S, in tetrahydrofuran and subsequently hydrolyzing the reaction mixture or quenching it with methyl iodide.