NOVEL CONVERSIONS OF BENZOTRIAZOL-1-YLMETHYL DERIVATIVES

被引：18

作者：

KATRITZKY, AR ^{[1
]}

WU, J ^{[1
]}

WROBEL, L ^{[1
]}

RACHWAL, S ^{[1
]}

STEEL, PJ ^{[1
]}

机构：

[1] UNIV CANTERBURY,DEPT CHEM,CHRISTCHURCH 1,NEW ZEALAND

来源：

ACTA CHEMICA SCANDINAVICA | 1993年 / 47卷 / 02期

关键词：

D O I：

10.3891/acta.chem.scand.47-0167

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

New (benzotriazol-1-yl)methyl derivatives of type BtCH2 X (X = Br, I, ONO2) have been investigated. Ethyl (benzotriazol-1-yl)acetate (BtCH2CO2Et) is converted by treatment with butyl nitrite into the oximes BtCH:NOH of which the E isomer is stable but the Z isomer rapidly undergoes rearrangement to (benzotriazol-1-yl)formamide. X-Ray crystallography proves the structures of the E isomer and the amide. Investigation of reactivity of the carbonyl and methylene groups in (benzotriazol-1-yl)acetophenone (BtCH2COPh) led to further interesting transformations.

引用

页码：167 / 175

页数：9

共 12 条

[1] PROOF OF STRUCTURES DERIVED FROM THE HYDROXY-METHYLATION AND AMINO-METHYLATION OF BENZOTRIAZOLE [J].

BURCKHALTER, JH ;

STEPHENS, VC ;

HALL, LAR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (15) :3868-3870

[2]

DONARUMA LG, 1960, ORGANIC REACTIONS, V11, pCH1

[3] POLYAZOLYLMETHANES .7. C-13 NMR-STUDY OF POLYPHENYL-METHANES, POLY-N-AZOLYL-METHANES AND POLY-N-BENZAZOYL-METHANES [J].

ELGUERO, J ;

CLARAMUNT, RM ;

GARCERAN, R ;

JULIA, S ;

AVILA, L ;

DELMAZO, JM .

MAGNETIC RESONANCE IN CHEMISTRY, 1987, 25 (03) :260-268

[4]

Fries K, 1934, LIEBIGS ANN CHEM, V511, P213

[5] SYNTHESIS OF QUINOXALINE DERIVATIVES THROUGH CONDENSATION OF 1,2-DIAMINOBENZENES WITH BETA-KETO SULFOXIDES [J].

KANO, S ;

SHIBUYA, S ;

YUASA, Y .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (07) :1559-1561

[6] THE FORMATION OF KETONES BY A REACTION EQUIVALENT TO R-+R'COCH2+-]R'COCH2R [J].

KATRITZKY, AR ;

WROBEL, L ;

SAVAGE, GP ;

DEYRUPDREWNIAK, M .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (01) :133-139

[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] BENZOTRIAZOLE - A NOVEL SYNTHETIC AUXILIARY [J].

KATRITZKY, AR ;

RACHWAL, S ;

HITCHINGS, GJ .

TETRAHEDRON, 1991, 47 (16-17) :2683-2732

[9]

Krollpfeiffer F, 1935, LIEBIGS ANN CHEM, V515, P113

[10]

PADWA A, 1984, COMPREHENSIVE HETERO, V7, P85

← 1 2 →