Lossen Rearrangements under Heck Reaction Conditions

被引：23

作者：

AbdelHafez, El-Shimaa M. N. ^{[1
]}

Aly, Omar M. ^{[2
]}

Abuo-Rahma, Gamal El-Din A. A. ^{[2
]}

King, S. Bruce ^{[1
]}

机构：

[1] Wake Forest Univ, Dept Chem, Winston Salem, NC 27106 USA

[2] Menia Univ, Dept Med Chem, Fac Pharm, Al Minya, Egypt

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 16期

关键词：

anilines; Heck reaction; hydroxamic acids; Lossen rearrangement; metal catalysis; ureas; HYDROXAMIC ACIDS; MONOHYDROXAMIC ACIDS; DIHYDROXAMIC ACIDS; UREAS; CHLORIDE; AMINES;

D O I：

10.1002/adsc.201400170

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The classical Lossen rearrangement converts activated hydroxamic acids to isocyanates that form numerous products upon their reaction with nucleophiles. We report a simple and highly efficient method of using Heck reaction conditions to initiate Lossen rearrangements of hydroxamic acids. In addition, Lossen rearrangements occur in the presence of palladium(II) acetate or triethylamine, components of the Heck reaction, alone. A potential mechanism is provided to explain this reactivity and these results show that Heck reactions and Lossen rearrangements occur under the same conditions and may provide new methods for facile initiation of Lossen rearrangements.

引用

页码：3456 / 3464

页数：9

共 41 条

[1] Regioselective preparation of pyridin-2-yl ureas from 2-chloropyridines catalyzed by Pd(0) [J].

Abad, A ;

Agulló, C ;

Cuñat, AC ;

Vilanova, C .

SYNTHESIS-STUTTGART, 2005, (06) :915-924

[2] A FACILE PREPARATION OF ALIPHATIC HYDROXAMIC ACID FROM N,N,O-TRIS (TRIMETHYLSILYL) HYDROXYLAMINE AND ACID CHLORIDE [J].

ANDO, W ;

TSUMAKI, H .

SYNTHETIC COMMUNICATIONS, 1983, 13 (12) :1053-1056

[3]

[Anonymous], 1974, ANGEW CHEM INT ED EN, V13, P376

[4] CONVERSION OF CARBOXYLIC ACIDS TO AMINES + THEIR DERIVATIVES [J].

BACHMAN, GB ;

GOLDMACH.JE .

JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (09) :2576-&

[5]

Bauer L., 1974, Angew. Chem, V86, P419

[6]

BITTNER S, 1974, TETRAHEDRON LETT, P1965

[7] A NEW SYNTHESIS OF SUBSTITUTED BARBITURIC ACIDS [J].

BOSE, AK ;

GARRATT, S .

TETRAHEDRON, 1963, 19 (01) :85-&

[8] ACID-CATALYSED HYDROLYSIS AND PROTONATION BEHAVIOUR OF HYDROXAMIC ACIDS [J].

BUGLASS, AJ ;

HUDSON, K ;

TILLETT, JG .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (01) :123-&

[9] ZUR CHEMIE DER ENERGIEREICHEN PHOSPHATE .8. CARBAMYLPHOSPHATE [J].

CRAMER, F ;

WINTER, M .

CHEMISCHE BERICHTE-RECUEIL, 1959, 92 (11) :2761-2767

[10] SULFATION OF HYDROXAMIC ACIDS [J].

DANIHER, FA .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (10) :2908-&

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