Cyanogen Bromide as Dehydrosulfurizing Agent for the Synthesis of Nβ-Fmoc-Amino Alkyl Isonitriles from Nβ-Fmoc-Amino Alkyl Thioformamides

被引：2

作者：

Vishwanatha, T. M. ^{[1
]}

Hemantha, H. P. ^{[1
]}

Sureshbabu, V. V. ^{[1
]}

机构：

[1] Bangalore Univ, Peptide Res Lab, Dept Studies Chem, Bangalore 560001, Karnataka, India

来源：

SYNLETT | 2010年 / 07期

关键词：

N-beta-Fmoc-amino alkyl thioformamides; isonitriles; dehydrosulfurization; cyanogen bromide; 4-COMPONENT REACTION; NATURAL-PRODUCTS; BUILDING-BLOCKS; ISOCYANIDES; DERIVATIVES; ACIDS; ISOTHIOCYANATES; CONDENSATION; CHEMISTRY; MIMETICS;

D O I：

10.1055/s-0029-1219583

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthetically useful N-beta-Fmoc amino alkyl isonitriles are prepared conveniently from N-beta-Fmoc amino alkyl thioformamides via a cyanogen bromide mediated dehydrosulfurization. The reaction is fast, clean, and yields are good.

引用

页码：1096 / 1100

页数：5

共 45 条

[1] Direct synthesis of isothiocyanates from isonitriles by molybdenum-catalyzed sulfur transfer with elemental sulfur
Adam, W
Bargon, RM
Bosio, SG
Schenk, WA
Stalke, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) : 7037 - 7041
[2] ALEXANDER GZ, 2009, J ORG CHEM, V74, P884
[3] NEW PREPARATION OF ISOCYANIDES
APPEL, R
KLEINSTUCK, R
ZIEHN, KD
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (02) : 132 - +
[4] Efficient syntheses of 5-aminoalkyl-1H-tetrazoles and of polyamines incorporating tetrazole rings
Athanassopoulos, CM
Garnelis, T
Vahliotis, D
Papaioannou, D
[J]. ORGANIC LETTERS, 2005, 7 (04) : 561 - 564
[5] Facile synthesis of aliphatic isothiocyanates and thioureas on solid phase using peptide coupling reagents
Boas, U
Gertz, H
Christensen, JB
Heegaard, PMH
[J]. TETRAHEDRON LETTERS, 2004, 45 (02) : 269 - 272
[6] Synthesis of indole derivatives via isocyanides
Campo, J
García-Valverde, M
Marcaccini, S
Rojo, MJ
Torroba, T
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (05) : 757 - 765
[7] THE BENZOIN CONDENSATION CATALYSIS BY BIS(AZOLIN-2-YLIDENE)S AND BIS(AZOLIDIN-2-YLIDENE)S AND ITS INTERPRETATION WITHIN THE CONTEXT OF NUCLEOPHILIC CARBENE CHEMISTRY
CASTELLS, J
LOPEZCALAHORRA, F
GEIJO, F
PEREZDOLZ, R
BASSEDAS, M
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (03) : 715 - 720
[8] Glyco- and peptidomimetics from three-component Joullie-Ugi coupling show selective antiviral activity
Chapman, TM
Davies, IG
Gu, B
Block, TM
Scopes, DIC
Hay, PA
Courtney, SM
McNeill, LA
Schofield, CJ
Davis, BG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (02) : 506 - 507
[9] Synthesis of chiral 1,1'-iminodicarboxylic acid derivatives from alpha-amino acids, aldehydes, isocyanides, and alcohols by the diastereoselective five-center four-component reaction
Demharter, A
Horl, W
Herdtweck, E
Ugi, I
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (02): : 173 - 175
[10] Recent developments in isocyanide based multicomponent reactions in applied chemistry
Dömling, A
[J]. CHEMICAL REVIEWS, 2006, 106 (01) : 17 - 89

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