One-pot Cyclization Research Articles

The first 4-chloro-1,3-bis(trimethylsilyloxy)-1,3-diene and its application to the regioselective synthesis of chlorinated arenes

Chlorinated phenols, benzophenones, and butenolides are prepared by various one-pot cyclization reactions of the first 4-chloro-1,3-bis(trimethylsilyloxy)-1,3-butadiene.

Synthesis of functionalized diaryl sulfides based on regioselective one-pot cyclizations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes

Functionalized diaryl sulfides were prepared based on one-pot cyclizations of 1,3-bis(trimethylsilyloxy)-1,3-butadienes.

A Convenient One-Pot Preparation of N-Substituted 4-Phenylpiperidines

N-Substituted 4-phenylpiperidines were readily synthesized by one-pot cyclization of diols with amines via bis-triflate intermediates. The new synthesis under mild conditions gave various N-substituted 4-phenylpiperidines in moderate to good yields.

Structural Aspects of Iodine-Promoted One-Pot Cyclization of O-Bis(methylthio)stilbenes to Thieno[3,2-b]thiophene Derivatives: Synthetic Trials of Tetrathienoacenes from 1,2-Bis(3-methylthiothiophen-2-yl)ethenes

In this paper, attempted reactions for the synthesis of tetrathienoacenes from 1,2-bis(3-methylthiothiophen-2-yl)ethenes by the iodine-promoted one-pot cyclization reaction were described. X-Ray structural analyses of the precursors indicated that the failure of reactions is closely related to the molecular structures around the reaction moiety, in particular, the bond angles defined by the aromatic ring and the neighboring carbon atom in the ethene moiety. We speculate that the larger angles in the 1,2-bis(3-methylthiothiophen-2-yl)ethenes make the intramolecular nucleophilic attack of the methylthio groups to the iodonium intermediate difficult.

Synthesis of 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes by cyclization of 1,3-bis(silyl enol ethers) with quinazolines

A variety of functionalized 3,4-benzo-7-hydroxy-2,9-diazabicyclo[3.3.1]non-7-enes were prepared by one-pot cyclizations of 1,3-bis(silyl enol ethers) with quinazolines. The mechanism of the cyclization was studied by B3LYP/6-31G(d) density functional theory computations. The products could be functionalized by Suzuki cross-coupling reactions. The reaction of 1,3-bis(silyl enol ethers) with phthalazine afforded open-chain rather than cyclization products.

Synthesis of pyrazole-3-carboxylates and pyrazole-1,5-dicarboxylates by one-pot cyclization of hydrazone dianions with diethyl oxalate

The one-pot cyclization of hydrazone dianions with diethyl oxalate allows a convenient synthesis of pyrazole-3-carboxylates and pyrazole-1,5-dicarboxylates.

Regioselective synthesis of sterically encumbered diaryl ethers based on one-pot cyclizations of 4-aryloxy-1,3-bis(trimethylsilyloxy)-1,3-dienes

Sterically encumbered diaryl ethers are prepared based on formal [3+3] cyclizations of novel 4-aryloxy-1,3-bis(trimethylsilyloxy)-1,3-dienes.

One-Pot Cyclization of 2-Aminophenethyl Alcohols: A Novel and Direct Approach to the Synthesis of N-Acyl Indolines

A unique one-pot cyclization of 2-aminophenethyl alcohols with carboxylic acids in the presence of PPh3, CCl4, and NEt3 furnished the formation of N-acyl indolines in good to excellent yields. This new approach provides an efficient, scalable, low-cost, and direct access to the biologically important indolines which are further oxidizable to indoles and oxindoles.

Synthesis of 4-alkoxycarbonyl-butenolides by uncatalyzed one-pot cyclization of 1,3-bis(silyloxy)alk-1-enes with oxalyl chloride

3-Hydroxy-4-alkoxycarbonyl-butenolides were prepared by one-pot cyclizations of 1,3-bis(silyloxy)alk-1-enes with oxalyl chloride.

Synthesis of 7,8-Benzo-4-hydroxy-1,9-diazabicyclo[3.3.1]non-3-enes by Cyclization of 1,3-Bis(silyl enol ethers) with Quinazoline

Functionalized 7,8-benzo-4-hydroxy-1,9-diazabicyclo[3.3.1]non-3-enes were prepared by one-pot cyclization of 1,3-bis(silyl enol ethers) with quinazolines.

Total synthesis of siomycin A

We have succeeded in the total synthesis of siomycin A, a representative compound of the thiostrepton family of peptide antibiotics, featuring the one-pot cyclization–elongation of our strategic intermediates and the late-stage formations of the thiazoline and dehydroamino acid moieties.

Synthesis of Butenolides by One-Pot Cyclization Reactions of Silyl Enol Ethers with Oxalyl Chloride

Oxalyl chloride represents a versatile C2 building block for cyclization reactions. A variety of cyclization reactions of oxalyl chloride are known which involve the formation of two carbon-heteroatom bonds. In contrast, one-pot cyclizations of oxalyl derivatives which proceed by formation of at least one carbon-carbon bond are more rare. In recent years, a number of such cyclizations have been developed which rely on the reaction of oxalyl chloride with silyl enol ethers. These reactions allow for an efficient synthesis of various oxygen heterocycles, such as γ-alkylidenebutenolides, maleic anhydrides and isotetronic acids. The cyclization reactions, which involve the formation of a carbon-carbon and a carbon-oxygen bond, generally proceed with excellent regioselectivity.

Synthesis of 2‐Oxo‐2,3,5,6‐tetrahydro‐5‐thioxoimidazo[1,2‐c]quinazolines by One‐Pot Cyclization of α‐Aminocarboxylic Esters with 2‐(Isothiocyanato)benzonitrile (ITCB).

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

One‐Pot Cyclization of Dilithiated Nitriles with Isothiocyanates and Epibromohydrin. Synthesis of 2‐Cyano‐1‐(hydroxymethyl)cyclopropanes and 2‐Cyanomethylidene‐4‐(hydroxymethyl)thiazolidines.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

Intermolecular one-pot cyclization of formyl-pyrroles of amino acid esters with norephedrine: stereoselective routes to new tricyclic pyrrole–pyrazine–oxazole fused structures

The treatment of esters of amino acids with dimethoxytetrahydrofuran furnished pyrrole derivatives of amino acid esters. The Wilsmeier–Haack formylation followed by the reaction of the formylated pyrroles with norephedrine afforded a selective formation of the tricyclic pyrrole–pyrazine–oxazole fused structures in one step via the formation of an oxazoline structure and intramolecular lactam formation. Pyrrole–pyrazine–oxazole fused structures were achieved in good yields. The cyclization reaction for the formation of an oxazole ring worked selectively to form only one stereoisomer. The configuration of the newly generated stereogenic center in the oxazole ring is dependent on the stereogenic centers of norephedrine.

A simple one-pot entry to cyclic ethers of varied ring sizes from diols via phosphonium ion induced iodination and base catalyzed Williamson etherification

A novel and an efficient one-pot cyclization method using triphenylphosphine, iodine and a nitrogenous base has been established for the synthesis of cyclic ethers of various ring sizes. This appears to follow a two-step procedure, which includes preferential substitution of one hydroxyl group by an iodide generated in situ followed by an intramolecular ring closure through the attack of a free hydroxyl group or the more nucleophilic oxide ion.

One-Pot Cyclization of Carbon Nucleophiles with 2-Isothiocyanatobenzoni­trile (ITCB): Synthesis of 4-Alkylidene-3,4-dihydroquinazoline-2(1H)thiones

The one-pot cyclization of 2-isothiocyanatobenzonitrile (ITCB) with carbon nucleophiles afforded 4-alkylidene-3,4-dihy­droquinazoline-2(1H)thiones with very good E diastereoselectivity.

Synthesis of 2-oxo-2,3,5,6-tetrahydro-5-thioxoimidazo[1,2- c]quinazolines by one-pot cyclization of α-aminocarboxylic esters with 2-(isothiocyanato)benzonitrile (ITCB)

The cyclization of 2-(isothiocyanato)benzonitrile with α-aminocarboxylic esters and acids afforded a variety of 2-oxo-2,3,5,6-tetrahydro-5-thioxo-imidazo[1,2- c]quinazolines with very good regioselectivity.

One-pot cyclization of dilithiated nitriles with isothiocyanates and epibromohydrin. Synthesis of 2-cyano-1-(hydroxymethyl)cyclopropanes and 2-cyanomethylidene-4-(hydroxymethyl)thiazolidines

Abstract The cyclization of dilithiated nitriles with epibromohydrin afforded 2-cyano-1-(hydroxymethyl)cyclopropanes. 2-Cyanomethylidene-(4-hydroxymethyl)thiazolidines were prepared by one-pot cyclization of dilithiated nitriles with isothiocyanates and epibromohydrin.

Microwave-Assisted Preparation of Fused Bicyclic Heteroaryl Boronates: Application in One-Pot Suzuki Couplings

The rapid and efficient synthesis of various disubstituted 5,6-fused heterocycles using a microwave-assisted one-pot cyclization-Suzuki coupling approach is described. This work highlights the tolerance of the boronic ester functional group to a variety of reaction conditions and the utility of functionalized boronates as penultimate intermediates in the synthesis of diverse compound libraries.