A novel annulation reaction of N-substituted-2-nitrosoanilines with esters of α-isocyano acids. A one-pot, two-step route to 2-benzimidazole-substituted esters of α-amino acids

被引：8

作者：

Bujok, Robert ^{[1
]}

Cmoch, Piotr ^{[1
]}

Wrobel, Zbigniew ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw 42, Poland

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 23期

关键词：

Heterocycles; Nitroso group; Isocyanides; Cyclization; 3-COMPONENT REACTION; EFFICIENT; CYCLOADDITION; CONDENSATION; INHIBITORS;

D O I：

10.1016/j.tetlet.2014.04.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A BF3-promoted cc-addition of isocyanides to both nitrogen atoms of N-aryl-2-nitrosoanilines leads to stable BF3-complexes of 3-N-hydroxy-(2-alkylimino)benzimidazole derivatives, which, after reduction with Zn in AcOH produce 1-N-ary1-2-alkylaminobenzimidazoles. This two-step annulation proceeds efficiently in a one-pot protocol with isocyanides derived from esters of alpha-amino acids. The chirality of the latter remains unaffected in the reaction. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：3410 / 3413

页数：4

共 52 条

[11] A resource-efficient and highly flexible procedure for a three-component synthesis of 2-imidazolines [J].

Elders, Niels ;

Schmitz, Rob F. ;

de Kanter, Frans J. J. ;

Ruijter, Eelco ;

Groen, Marinus B. ;

Orru, Romano V. A. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :6135-6142

[12]

Grant F. S., 2000, [No title captured], Patent No. [WO0043371, 0043371]

[13] DIAZIRIDINONES .4. FORMATION BY CONDENSATION OF ALKYL ISOCYANIDE WITH NITROSOALKANE . EVIDENCE FOR A CARBODIIMIDE N-OXIDE [J].

GREENE, FD ;

PAZOS, JF .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (08) :2269-&

[14] Isocyanoacetate Derivatives: Synthesis, Reactivity, and Application [J].

Gulevich, Anton V. ;

Zhdanko, Alexander G. ;

Orru, Romano V. A. ;

Nenajdenko, Valentine G. .

CHEMICAL REVIEWS, 2010, 110 (09) :5235-5331

[15] Convergent multicomponent assembly of 2-acyloxymethyl thiazoles [J].

Henkel, B ;

Beck, B ;

Westner, B ;

Mejat, B ;

Dömling, A .

TETRAHEDRON LETTERS, 2003, 44 (50) :8947-8950

[16] A novel three-component reaction for the synthesis of N-cyclohexyl-3-aryl-quinoxaline-2-amines [J].

Heravi, Majid M. ;

Baghernejad, Bita ;

Oskooie, Hossein A. .

TETRAHEDRON LETTERS, 2009, 50 (07) :767-769

[17]

Janssens F. E., 2001, [No title captured], Patent No. [WO0100615, 0100615]

[18] High-throughput screening system for catalytic hydrogen-producing materials [J].

Jaramillo, TF ;

Ivanovskaya, A ;

McFarland, EW .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (01) :17-22

[19] ATROPISOMERISM IN POLYMERS - SCREW-SENSE SELECTIVE POLYMERIZATION OF ISOCYANIDES BY INHIBITING THE GROWTH OF ONE ENANTIOMER OF A RACEMIC PAIR OF HELICES [J].

KAMER, PCJ ;

CLEIJ, MC ;

NOLTE, RJM ;

HARADA, T ;

HEZEMANS, AMF ;

DRENTH, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (05) :1581-1587

[20]

Kemp M. I., 2002, [No title captured], Patent No. [US6372736, 6372736]

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