Syntheses of dialkyl and functionalized ketones via 1-(benzotriazol-1-yl)alkyl methyl thioethers

被引：22

作者：

Katritzky, AR ^{[1
]}

Oniciu, DC ^{[1
]}

Ghiviriga, I ^{[1
]}

Soti, F ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 07期

关键词：

D O I：

10.1021/jo971389k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzotriazol-1-ylmethyl methyl thioether (1), after easy deprotonation by BuLi, reacted with alkyl halides to afford 1-(benzotriazol-1-yl)alkyl methyl thioethers 2 in good yields. The utility of compounds 2 as alkanoyl anion equivalents was demonstrated by the reactions of their anions with alkyl halides, aldehydes, ketones, esters, and phenyl isocyanate: the products were readily hydrolyzed to alpha-functionalized ketones in dilute aqueous acid.

引用

页码：2110 / 2115

页数：6

共 29 条

[1]

Ager D. J., 1987, UMPOLED SYNTHONS, P19

[2]

ALTENBACH HJ, 1991, COMPREHENSIVE ORGANI, V6, P829

[3]

Bloomfield J. J., 1976, ORG REACTIONS, V23, P259

[4] CLEMMENSEN REDUCTION .7. ACID-CATALYZED OPENING OF CYCLOPROPANE-1,2-DIOLS [J].

DAVIS, BR ;

REWCASTLE, GW ;

WOODGATE, PD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (11) :2820-2825

[5]

FUJITA T, 1978, J APPL CHEM BIOTECHN, V28, P882

[6] UNTERSUCHUNGEN IN DER AZOLREIHE .1. DARSTELLUNG UND EIGENSCHAFTEN VON OXAZOLONEN-(2) [J].

GOMPPER, R .

CHEMISCHE BERICHTE-RECUEIL, 1956, 89 (07) :1748-1762

[7] VINYL CATIONS .40. PI-ROUTES AND SIGMA-ROUTES TO VINYL CATIONS - SOLVOLYSES OF 2-METHYLCYCLOHEXENYL, CYCLOPENTYLIDENEETHYL, HEX-5-YN-1-YL, AND RELATED TRIFLATES [J].

HANACK, M ;

FUCHS, KA ;

COLLINS, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (12) :4008-4017

[8]

Hassner A., 1991, COMPREHENSIVE ORGANI, P541, DOI DOI 10.1016/B978-0-08-052349-1.00017-2

[9] SYNTHESIS OF CIS AND TRANS WHISKY AND COGNAC LACTONES BY THE REGIOCONTROLLED ALKYLATION OF 2-(TRIMETHYLSILOXY)FURAN [J].

JEFFORD, CW ;

SLEDESKI, AW ;

BOUKOUVALAS, J .

HELVETICA CHIMICA ACTA, 1989, 72 (06) :1362-1370

[10] Novel and facile syntheses of alkenyl, alkynyl, and aryl 1,2-diketones [J].

Katritzky, AR ;

Wang, ZQ ;

Lang, HY ;

Feng, DM .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :4125-4130

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