Linghong Xie

Synthesis of primary amines via nucleophilic addition of organometallic reagents to aldimines on solid support

Abstract Resin-immobilized aldimines 5 , derived from the condensation of amine-functionalized Rink polystyrene resin with aldehydes, react with Grignard reagents, lithium reagents or LiBH 4 to afford a wide variety of primary amines in good to excellent yields upon trifluoroacetic acid cleavage. In this amine synthesis, Rink resin functions both as a solid support and as a NH protecting group.

A General and Convenient Synthesis of N-[(1. Diphenyl-oxophosphinyl)alkyl]carboxamides and Sulfamide

Abstract A wide range of title compounds were prepared in good yields by amidoalkylation of ethyl diphenylphosphinite with readily available N-α-(benzotriazol-1-yl)alkyl]amides. A more convenient direct one-pot amidoalkylation of ethyl diphenylphosphinite with an amide, an aldehyde and benzotriazole is described.

A Versatile Synthesis of 3-Substituted Indoles

Abstract A variety of 3-substituted indoles are prepared from 1-methyl-3-(benzotriazol-1-ylalkyl)indoles (1), which are readily available either from the condensation of 3-methylindole with N-(benzotriazol-1-ylalkyl)carbamates or from the alkylation and silylation of lithiated 1-methyl-3-(benzotriazol-1-ylmethyl)indole (2).

Novel tele nucleophilic aromatic substitutions in α-(benzotriazol-1-yl)alkyl aryl ketones☆

Abstract Reactions of α-(benzotriazol-1-yl)alkyl aryl ketones 2 with alkyllithiums or Grignard reagents afforded para-alkylated products 5, via novel tele nucleophilic aromatic substitutions.

NOVEL ROUTE TO FUNCTIONALIZED INDANS VIA FORMAL 3 + 2 CYCLOADDITIONS OF 1-BENZYLBENZOTRIAZOLES WITH ALKENES

Abstract α-Functionalized 1-benzylbenzotriazoles (3, 4 and 12), derived from the lithiation of 1-(2,3-dimethoxybenzyl)benzotriazole 2 followed by reactions with electrophiles, or from the condensation of benzyl alcohol 11 with benzotriazole, undergo formal [3 + 2] cycloadditions with styrenes upon treatment with ZnBr2 to give functionalized indans (9, 10, 13 and 14).

Synthesis of 5,6-dihydro-4H-pyrido[3,2,1-jk]carbazolesvia intermolecular [4+2] cycloaddition

4-, 4,5- and 4,6-Substituted 5,6-dihydro-4H-pyrido[3,2,1-jk]carbazoles are synthesized regioselectively from carbazole by a novel, two step sequence.

THE REACTIONS OF SOME ALKOXYCARBONYL ISOTHIOCYANATES WITH ALCOHOLS, PHENOLS AND AMINES

(1993). THE REACTIONS OF SOME ALKOXYCARBONYL ISOTHIOCYANATES WITH ALCOHOLS, PHENOLS AND AMINES. Organic Preparations and Procedures International: Vol. 25, No. 1, pp. 83-90.

Convenient one-pot method for the preparation of polysubstituted benzo[b]- and naphtho[1,2-b]-furans and -thiophenes

N-(Phenoxymethyl)- and N-(phenylthiomethyl)-benzotriazoles are versatile substrates for the preparation of benzofurans and benzothiophenes by insertion reactions of their anions into alkyl and aryl aldehydes and in situ cyclization of the α-aryloxy and α-arylthio ketones thus formed. N-(Naphthyloxy)- and N-(naphthylthio)-benzotriazoles are similarly efficient precursors for naphthofurans and naphthothiophenes.