An improved synthesis of N-Boc protected aryl amines

被引：53

作者：

Darnbrough, S ^{[1
]}

Mervic, M ^{[1
]}

Condon, SM ^{[1
]}

Burns, CJ ^{[1
]}

机构：

[1] Aventis Pharmaceut, Dept Med Chem, Collegeville, PA 19426 USA

来源：

SYNTHETIC COMMUNICATIONS | 2001年 / 31卷 / 21期

关键词：

D O I：

10.1081/SCC-100106036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

There are several known methods of protecting amines as their Boc derivatives. For less nucleophilic amines such as aryl amines these methods often give poor yields and are generally not satisfactory. Here, Boc aryl amines are obtained by first introducing two Boc groups followed by selective removal of one of them. This procedure works well for a number highly sterically hindered substrates as well as electron deficient and electron rich aryl amines.

引用

页码：3273 / 3280

页数：8

共 17 条

[1] SELECTIVELY PROTECTED CHIRAL 1,2,4-TRIAMINOBUTANES AND CHIRAL VICINAL 1,2-DIAMINES [J].

ALTMAN, J ;

BENISHAI, D ;

BECK, W .

TETRAHEDRON-ASYMMETRY, 1994, 5 (05) :887-894

[2] DEVELOPMENT OF NEW DNA-BINDING AND CLEAVING MOLECULES - DESIGN, SYNTHESIS AND ACTIVITY OF A BISDIAZONIUM SALT [J].

ARYA, DP ;

WARNER, PM ;

JEBARATNAM, DJ .

TETRAHEDRON LETTERS, 1993, 34 (49) :7823-7826

[3] IONIZATION CONSTANTS OF HETEROCYCLIC SUBSTANCES .9. PROTONATION OF AMINOPYRIDONES AND AMINOPYRIMIDONES [J].

BARLIN, GB ;

PFLEIDER.W .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (07) :1425-&

[4] AN EFFICIENT SYNTHESIS OF 1,2,9,9A-TETRAHYDROCYCLOPROPA[C]BENZ[E]INDOL-4-ONE (CBI) - AN ENHANCED AND SIMPLIFIED ANALOG OF THE CC-1065 AND DUOCARMYCIN ALKYLATION SUBUNITS [J].

BOGER, DL ;

MCKIE, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1271-1275

[5] Enantioselective total synthesis of (+)-duocarmycin A, epi-(+)-duocarmycin A, and their unnatural enantiomers [J].

Boger, DL ;

McKie, JA ;

Nishi, T ;

Ogiku, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (09) :2301-2302

[6] REMOVAL OF FORMYL, ACETYL, AND BENZOYL GROUPS FROM AMIDES WITH CONVERSION INTO THE CORRESPONDING TERT-BUTYL CARBAMATES [J].

GREHN, L ;

GUNNARSSON, K ;

RAGNARSSON, U .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (19) :1317-1318

[7] A SIMPLE METHOD FOR THE PROTECTION OF ARYL AMINES AS THEIR T-BUTYLCARBAMOYL (BOC) DERIVATIVES [J].

KELLY, TA ;

MCNEIL, DW .

TETRAHEDRON LETTERS, 1994, 35 (48) :9003-9006

[8]

Lamothe M, 1996, SYNLETT, P507

[9]

MAEDA H, 1988, CHEM PHARM BULL, V36, P190

[10] ORTHO FUNCTIONALIZATION OF N-(TERT-BUTOXYCARBONYL)ANILINE [J].

MUCHOWSKI, JM ;

VENUTI, MC .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (23) :4798-4801

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