To each his own: isonitriles for all flavors. Functionalized isocyanides as valuable tools in organic synthesis

被引:356
作者
Giustiniano, Mariateresa [1 ]
Basso, Andrea [2 ]
Mercalli, Valentina [3 ]
Massarotti, Alberto [3 ]
Novellino, Ettore [1 ]
Tron, Gian Cesare [3 ]
Zhu, Jieping [4 ]
机构
[1] Univ Napoli Federico II, Dipartimento Farm, Via D Montesano 49, I-80131 Naples, Italy
[2] Univ Genoa, Dipartimento Chim & Chim Ind, Via Dodecaneso 31, I-16143 Genoa, Italy
[3] Univ Piemonte Orientale, Dipartimento Sci Farmaco, Largo Donegani 2, I-28100 Novara, Italy
[4] Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Synth & Nat Prod, EPFL SB ISIC LSPN,BCH 5304, CH-1015 Lausanne, Switzerland
关键词
ALPHA-METALATED ISOCYANIDES; ONE-POT SYNTHESIS; PROMOTED 3-COMPONENT SYNTHESIS; ASYMMETRIC ALDOL REACTION; ACID-CATALYZED REACTIONS; TERT-BUTYL ISOCYANIDE; C BOND FORMATION; UGI; 4-COMPONENT; MULTICOMPONENT SYNTHESIS; CONVENIENT SYNTHESIS;
D O I
10.1039/c6cs00444j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The term functionalized isocyanides refers to all those isocyanides in which a neighbouring functional group can finely tune the reactivity of the isocyano group or can be exploited in post-functionalization processes. In this manuscript, we have reviewed all the isocyanides in which the pendant functional group causes either deviation from or reinforces the normal reactivity of the isocyano group and categorized them to highlight their common features and differences. An analysis of their synthetic potential and the possible unexplored directions for future research studies is also addressed.
引用
收藏
页码:1295 / 1357
页数:63
相关论文
共 426 条
[21]   One-pot synthesis and biological evaluation of aspergillamides and analogues [J].
Beck, B ;
Hess, S ;
Dömling, A .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (15) :1701-1705
[22]   UBER TRIORGANOMETALLFULMINATE VON SILICIUM GERMANIUM ZINN UND BLEI [J].
BECK, W ;
SCHUIERE.E .
CHEMISCHE BERICHTE-RECUEIL, 1964, 97 (12) :3517-&
[23]  
Bergemann M, 1998, SYNTHESIS-STUTTGART, P1437
[24]  
Bergemann M, 1999, HELV CHIM ACTA, V82, P909, DOI 10.1002/(SICI)1522-2675(19990609)82:6<909::AID-HLCA909>3.3.CO
[25]  
2-K
[26]  
Bergemann M, 1996, SYNTHESIS-STUTTGART, P975
[27]  
Bergemann M., 2002, HELV CHIM ACTA, V85, P2222
[28]   Synthesis of rigid hydrophobic tetrazoles using an Ugi multi-component heterocyclic condensation [J].
Bienaymé, H ;
Bouzid, K .
TETRAHEDRON LETTERS, 1998, 39 (18) :2735-2738
[29]   Reagent explosion:: an efficient method to increase library size and diversity. [J].
Bienaymé, H .
TETRAHEDRON LETTERS, 1998, 39 (24) :4255-4258
[30]   An improved synthesis of N-isocyanoiminotriphenylphosphorane and its use in the preparation of diazoketones [J].
Bio, MM ;
Javadi, G ;
Song, ZJ .
SYNTHESIS-STUTTGART, 2005, (01) :19-21