Antonio Arcelli

Selective conversion of primary amines into N,N-dimethylalkyl- or N,N-dialkylmethyl-amines with methanol and RuCl2(Ph3P)3

N,N-dimethylalkyl- or N,N-dialkylmethyl-amines are selectively obtained from the reaction between aliphatic amines and methanol at 180°C for 7 h in the presence of RuCl2(Ph3P)3 catalyst.

Selective reduction of aldehydes by a formic acid-trialkylamine-RuCl2 (pph3)3 system

Abstract In the presence of trialkylamine and formic acid RuCl 2 (PPh 3 ) 3 selectively reduces aldehydes to the corresponding alcohols at room temperature. Other reducible groups are unaffected.

The homogeneously catalysed synthesis of N-methyldi-alkylamines from n-methyl and N,N-dimethylalkylamines

Abstract N-Methyl and N,N-dimethylalkylamines are converted into N-methyldialkyl-amines in good yields when heated at 180°C in the presence of a catalytic amount of RuCl 2 (Ph 3 P) 3- .

Synthesis and glycosidase inhibition of new enantiopure 2,3-diamino conduritols

Abstract A new 2,3-diamino conduritol, isoster of conduritol F, was obtained starting from d -sorbitol. In the synthetic sequence an unprecedented transannular cyclization led, as a side product, to a bicyclic compound bearing a cyclopropyl ring. The synthesis of the completely deprotected 2,3-diamino conduritol, isoster of conduritol B, was devised via the intermediate O-benzylation of the OH groups. The O-methylated and deprotected 2,3-diamino conduritols were evaluated as inhibitors of α- and β-glucosidase.

Synthesis and biological activity of the (−)-(2R,3S,4S)-3-azido-4-methoxy-2-(1′S-methoxy-2′-azido)ethyl-thiolane

Abstract A stereospecific ring contraction reaction, promoted by NaN3, was detected starting from a thiepane derivative obtained from d -sorbitol, an inexpensive alcohol sugar. The major polyfunctionalized thiolane derivative obtained was investigated as a potential glycosidase inhibitor.

Stereo- and chemoselective transfer hydrogenation of carbonyl groups with RuCl2(PPh3)3 and BINAP-Ru as catalysts and Et3NH+H2PO2−·1,5H2O as a hydrogen donor

Using Et3NH+H2PO2−.1.5 H2O as a hydrogen donor, the RuCl2(Ph3P)3, RuCl2(PPh3)3C and BINAP-Ru proved highly active catalysts for transfer hydrogenation of ketones under milder conditions than other hydrogen donors. 2-Methyl-, 2-chloro-, 2-(ethoxy-carbonyl)cyclohexanones and -cyclopentanones were reduced to the less stable axial alcohols in excellent diastereoisomeric excess (de: 90–100%), and the carbonyl group of α,β-unsaturated ketones was selectively reduced, in contrast with other hydrogen donors the CC bond was reduced.

RuCl2(PPh3)3/HCOOH/Et3N as a new hydrogen source. Selective reduction of aromatic nitro compounds catalysed by Pd on carbon

Abstract Pd on carbon increases the reactivity of the system RuCl 2 (PPh 3 ) 3 /HCOOH/Et 3 N and induces selective reduction of nitroaromatic compounds which is faster than that of olefins or haloaromatic derivatives. Other potentially reducible groups do not react.

Homogeneous transition-metal catalysis. Cleavage of the CN bond of tertiary amines by acid anhydrides in the presence of transition metal ions

Abstract In the presence of transition metal chlorides, acid anhydrides are highly active in promoting the dealkylation of tertiary amines, and good yields of N , N -dialkylamides are obtained.

Synthesis of new enantiopure thiepane derivatives and their evaluation as glycosidase inhibitors

Starting from inexpensive alcohol sugars we have synthesised a series of oxygen- and nitrogen-containing enantiopure thiepanes to investigate the structural and stereochemical requirements for inhibitory activity against a variety of glycosidases. An interesting trend was observed on analysis of the biological screening results for these derivatives.

Unusual ammonolysis of a secondary amide assisted by unsubstituted vicinal amide group

Abstract Evidence for the participation of neighboring -CONH 2 group in the ammonolysis of disubstituted amide was obtained. The surprising conversion of 1 into 3 in very mild conditions is a process formed by two consecutive first order reactions. Kinetics were performed in ethanol at various temperatures and NH 3 concentrations. The ammonolysis of the isolated intermediate 2 allowed the unambiguous attribution of k 1 and k 2 to steps 1→2 and 2→3 , respectively (Scheme 1). The thermodynamic parameters of activation for both steps of the process were evaluated.