CYANOMETHYL GROUP - A VERSATILE PROTECTING GROUP FOR PHENOLS, PRIMARY AND SECONDARY-AMINES, AND CARBAMATES

被引：11

作者：

BENARAB, A ^{[1
]}

BOYE, S ^{[1
]}

SAVELON, L ^{[1
]}

GUILLAUMET, G ^{[1
]}

机构：

[1] UNIV ORLEANS,CNRS,CHIM BIOORGAN & ANALYT LAB,BP 6759,F-45067 ORLEANS 2,FRANCE

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 47期

关键词：

D O I：

10.1016/S0040-4039(00)60401-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of the cyanomethyl unit as a protecting group for phenols, primary and secondary amines, and carbamates is described. Optimized conditions for formation and hydrolysis of cyanomethyl in the presence of the other hydrogenolysis-sensitive groups such as O- and N-benzyl groups are presented.

引用

页码：7567 / 7568

页数：2

共 7 条

[1] NOVEL NONOPIOID NON-ANTIINFLAMMATORY ANALGESICS - 3-(AMINOALKYL) AND 3-[(4-ARYL-1-PIPERAZINYL)ALKYL]OXAZOLO[4,5-B]PYRIDIN-2(3H)-ONES [J].

FLOUZAT, C ;

BRESSON, Y ;

MATTIO, A ;

BONNET, J ;

GUILLAUMET, G .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (04) :497-503

[2] SYNTHESIS OF (+/-)-PREPINNATERPENE, A BROMODITERPENE FROM THE RED ALGA LAURENCIA-PINNATA YAMADA [J].

FUKUZAWA, A ;

SATO, H ;

MASAMUNE, T .

TETRAHEDRON LETTERS, 1987, 28 (37) :4303-4306

[3] SYNTHESIS OF ANGULAR DIOXINOCOUMARINS [J].

GUILLAUMET, G ;

HRETANI, M ;

COUDERT, G .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (01) :193-197

[4] CYANOMETHYL ESTERS - USEFUL PROTECTION FOR CARBOXYLIC-ACIDS [J].

HUGEL, HM ;

BHASKAR, KV ;

LONGMORE, RW .

SYNTHETIC COMMUNICATIONS, 1992, 22 (05) :693-697

[5]

MALEN C, 1970, Patent No. 2017902

[6] SYNTHESIS APPLICATIONS OF CATIONIC AZA-COPE REARRANGEMENTS .23. 1ST TOTAL SYNTHESIS OF AMARYLLIDACEAE ALKALOIDS OF THE 5,11-METHANOMORPHANTHRIDINE TYPE - AN EFFICIENT TOTAL SYNTHESIS OF (+/-)-PANCRACINE [J].

OVERMAN, LE ;

SHIM, J .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (17) :5005-5007

[7] SYNTHESIS APPLICATIONS OF AZA-COPE REARRANGEMENTS .11. CARBON CARBON BOND FORMATION UNDER MILD CONDITIONS VIA TANDEM CATIONIC AZA-COPE REARRANGEMENT MANNICH REACTIONS - A CONVENIENT SYNTHESIS OF POLYSUBSTITUTED PYRROLIDINES [J].

OVERMAN, LE ;

KAKIMOTO, M ;

OKAZAKI, ME ;

MEIER, GP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (22) :6622-6629

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