6. New Synthetic Building Blocks

6.1 Domino Reactions of 2-Isothiocyanatobenzonitrile

Abstract: 2-Isothiocyanatobenzonitrile (ITCB) and isocyanatobenzonitrile (ICB) represent versatile synthetic building blocks containing a nitrile and an isothiocyanate or an isocyanate function, respectively. Domino reactions of ITCB and ICB provide a convenient access to a variety of pharmacologically important heterocycles.

Review: Curr. Org. Chem. 2009, 13, 955-964.

Period of investigation: 2002 – 2009

Keywords: domino reactions; cyclizations; heterocycles

6.2 Cyclizations of 1,1-Diacylcyclopropanes

Abstract: The cyclization of 1,1-diacylcyclopropanes with free and masked dianions provides spirocyclopropanes which readily undergo ring-cleavage reactions. Cyclopropylated 1,3,5-tricarbonyl compounds were prepared for the first time. Based on this work also other syntheses of cyclopropanes were developed.

Review: Synlett 2023, 34, 1765-1776.

Period of investigation: 2002 - 2011

Keywords: cyclopropanes; cyclizations; dianions; 1,3-dicarbonyl compounds

6.3 Cyclizations of Bis-Imidoylchlorides of Oxalic Acid

Abstract: The cyclization of oxaldiimidoyl dichlorides, readily available novel building blocks, with ambident dianions and other bis(nucleophiles), such as diamines, provides a convenient access to a variety of heterocycles important in medicinal chemistry or materials science. Reactions include cyclization-, domino-, one-pot- and double-anion-capture-reactions.

Review: Eur. J. Org. Chem. 2002, 221-234.

Period of investigation: 1999 – 2006

Keywords: cyclizations; dianions; heterocycles

6.4 Cyclizations of (2,4-Dioxobutylidene)phosphoranes

Abstract: (2,4-Dioxobutylidene)phosphoranes can be regarded as equivalents of 1,3-dicarbonyl dianions and represent versatile building blocks in one-pot cyclizations. Their reactions with various electrophiles, such as 1,3-dicarbonyl compounds, enones, a-halo ketones, or hydrazine derivatives, allow for a convenient synthesis of a variety of carbo- and heterocyclic ring systems.

Review: Synthesis 2008, 3877-3902.

Period of investigation: 2000 – 2007

Keywords: 1,3-dicarbonyl compounds; cyclizations; heterocycles; arenes