A convenient synthesis of new 1-alkynyl-1H-benzotriazoles by reaction of alkynyl(phenyl)iodonium salts with benzotriazole ion

被引：28

作者：

Kitamura, T ^{[1
]}

Tashi, N ^{[1
]}

Tsuda, K ^{[1
]}

Chen, HY ^{[1
]}

Fujiwara, Y ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch Engn, Dept Chem & Biochem, Fukuoka 8128581, Japan

来源：

HETEROCYCLES | 2000年 / 52卷 / 01期

关键词：

D O I：

10.3987/COM-99-S25

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of arylethynyl(phenyl)iodonium tosylates with benzotriazole ion gave new 1-alkynyl-1H-benzotriazoles in good yields. This result indicates that alkynyliodonium salts can be used for direct alkynylation of benzotriazole. However, the similar reactions of (tert-butylethynyl)(phenyl)iodonium and 1-octynyl(phenyl)iodonium tosylates do not afford the 1-alkynyl-1H-benzotriazoles but alkenylbenzotriazoles via the reaction of alkylidenecarbenes.

引用

页码：303 / 312

页数：10

共 42 条

[1] GENERATION AND TRAPPING OF AN ALKYNYL CATION [J].

ANGELINI, G ;

HANACK, M ;

VERMEHREN, J ;

SPERANZA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1298-1299

[2] FLASH-PYROLYSIS OF 1-VINYLBENZOTRIAZOLES [J].

BARKER, SJ ;

STORR, RC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03) :485-488

[3]

FAN WQ, 1996, COMPREHENSIVE HETERO, V4, P2

[4]

JONES WM, 1980, REARRANGEMENTS GROUN, V3

[5]

KATRITZKY AR, 1994, SYNTHESIS-STUTTGART, P445

[6]

KATRITZKY AR, 1992, LIEBIGS ANN CHEM, P843

[7] THE CHEMISTRY OF N-SUBSTITUTED BENZOTRIAZOLES .1. 1-(CHLOROMETHYL)-BENZOTRIAZOLE [J].

KATRITZKY, AR ;

RACHWAL, S ;

CASTER, KC ;

MAHNI, F ;

LAW, KW ;

RUBIO, O .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (04) :781-789

[8]

KATRITZKY AR, 1988, RECL TRAV CHIM PAY B, V107, P641

[9] THE CHEMISTRY OF N-SUBSTITUTED BENZOTRIAZOLES .7. THE ISOMERIC COMPOSITION AND MECHANISM OF INTERCONVERSION OF SOME N-(AMINOMETHYL)BENZOTRIAZOLE DERIVATIVES [J].

KATRITZKY, AR ;

YANNAKOPOULOU, K ;

KUZMIERKIEWICZ, W ;

AURRECOECHEA, JM ;

PALENIK, GJ ;

KOZIOL, AE ;

SZCZESNIAK, M ;

SKARJUNE, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12) :2673-2679

[10]

KATRITZKY AR, 1994, CHEM SOC REV, P363

← 1 2 3 4 5 →