Reformatsky Reaction of Methyl 1-Bromocyclohexanecarboxylate with N,N′-(1,4-Phenylene)bis(1-arylmethanimines)

Russian Journal of Organic Chemistry - Reformatsky reagent prepared from methyl 1-bromocyclohexanecarboxylate reacted with N,N′-(1,4-phenylene)bis(1-arylmethanimines) to produce...     

Reaction of 1-(2-Oxocyclohexyl)ethane-1,1,2,2-tetracarbonitrile with α,β-Unsaturated Aldehydes

Russian Journal of General Chemistry - The reaction of 1-(2-oxocyclohexyl)ethane-1,1,2,2-tetracarbonitrile with crotonic aldehyde, cinnamic aldehyde, 2-furylacrolein, 3-phenyl-2-propinal,...     

The Reaction of 1-Aryl-2-(4-nitrophenylsulfonyl)ethanones with α,β-Unsaturated Esters

1-Aryl-2-(4-nitrophenylsulfonyl)ethanones (1) reacted with one equiv. of α,β-unsaturated esters at 60°C to afford the tandem addition-rearrangement products (3), while at 75°C 1a reacted with two equiv. of methyl acrylate and gave an unexpected addition-rearrangement-addition-annulation product which is dimethyl 4-hydroxyl-1-(4-nitrophenyl)-4-phenyl-1,3-cyclohexyldicarboxylate (4). A mechanism is suggested.     

The Reaction of 1-Nitro-4-(4-nitrophenylsulfonylmethyl)benzene with α,β-Unsaturated Esters

Under solid-liquid PTC conditions, treatment of 1-nitro-4-(4-nitrophenylsulfonyl-methyl)benzene(1) with α,β -unsaturated esters (2a-h) at 35–75°C gave tandem addition-rearrangement products(3a-h). While at higher temperature(75°C), addition-rearrangement-addition products (4a-b) were obtained when acrylates were used. Finally a possible mechanism is proposed.     

Reaction of N,N′-Methylenebis(trifluoromethanesulfonamide) with Styrene under Oxidative Conditions

Russian Journal of Organic Chemistry - The reaction of N,N′-methylenebis(trifluoromethanesulfonamide) with styrene in the oxidative system t-BuOCl/NaI affords triflamide,...     

Synthesis of 3-acylated indoles through iron-catalyzed oxidative coupling of indoles with α-amino carbonyl compounds

A novel iron-catalyzed oxidative coupling of indoles with α-amino carbonyl compounds has been developed. The transformation provides an attractive approach to the synthesis of 3-acylindoles, with the advantages of easily available starting materials and high functional group tolerance. Furthermore, control experiments imply that a radical process maybe involved in this reaction.     

Reaction of Substituted Cyclopentadienyl-magnesium-Chloride with Carbonyl Compound ( Ⅰ )——Reaction of (1, 1-Dialkyl-3-Butenyl) Cyclopentadienyl-magnesium-chloride with Ketones

The substituted cyclopentadienyl-magnesium-chloride, obtained by exocyclic addition of 6,6-dialkylfulvene and allyl-magnesium-chloride, reacted with the ketone 3, the product was hydrolyzed and dehydrated to give the 2-(1 ,1-dialkyl-3-butenyl)-6,6-dialkyl-fulvene 5. The structure of 5 was determined by using the 1H NMR spectra of 5 and the adducts of 5 with tetracyanoethylene.     

Tandem Reaction of Deprotonation-Oxidation-Wittig Reaction: Stereoselective Synthesis of (E)-α,β-Unsaturated Enoates

Ｓｉｎｃｅｉｔｓｄｉｓｃｏｖｅｒｙ ,Ｗｉｔｔｉｇｒｅａｃｔｉｏｎｈａｓｂｅｃｏｍｅｏｎｅｏｆｐｒｉｍａｒｙｍｅｔｈｏｄｓｆｏｒｔｈｅｆｏｒｍａｔｉｏｎｏｆｃａｒｂｏｎ ｃａｒｂｏｎｄｏｕｂｌｅｂｏｎｄｓａｎｄｂｅｅｎｗｉｄｅｌｙｕｓｅｄｉｎｔｈｅｓｙｎｔｈｅｓｉｓｏｆｎａｔｕｒａｌｐｒｏｄｕｃｔｓ .1,2 Ｒｅｃｅｎｔｌｙ ,ｉｔｗａｓｆｏｕｎｄｔｈａｔｐｒｉｍａｒｙａｌｃｏｈｏｌｓｃａｎｕｎｄｅｒｇｏｔｈｅｔａｎｄｅｍｒｅａｃｔｉｏｎｏｆｏｘｉｄａｔｉｏｎ Ｗｉｔｔｉｇｒｅａｃｔｉｏｎｗｉｔｈｐｈｏｓ…     

Reaction of Lewisite-1 with Alcohols,Diols, and Thiols in Water—A Simple Method of Derivatization of Thiodiglycol

Reaction of 2-chlorovinyldichloroarsine (Lewisite-1) with alcohols, thiols, diols, and hydroxy thiols in water at 40°C has been examined. The expected derivatization products, dialkyl 2-chlorovinylarsonites or corresponding arsonodithiolites, were obtained with alcohols and thiols, whereas reactions with bifunctional diols and hydroxythiols produced analogous cyclic esters. All derivatives may be easily detected using gas chromatography. This reaction was found useful to easily transform bis(2-hydroxyethyl) sulfide (thiodiglycol), a sulfur mustard decomposition product, to a stable eight-membered cyclic arsonite derivative. After extraction with dichloromethane, the derivative may be easily and selectively detected using GC/MS at a 100 ppb level thiodiglycol content in water matrices, eliminating tedious evaporation of water and then silylation. This method may be applied to analyze Chemical Weapons Convention related environmental water samples.     

Reaction ofβ-arylacryloyloxiranes with phenylhydrazine

The reaction of -arylacryloyloxiranes with phenythydrazine under the conditions of acid catalysis leads to 3 arylvinyl-I-phenylpyrazoles and 2-hydroxymethyl-5-aryl-1,4-pentadien-3-one phenythydrazones.Belorussian State Technological University. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3 pp. 324–327, March, 1996. Original article submitted June 26, 1995.     

Synthesis of Macroheterocycles by Reaction of N,N′-(1,4-Phenylene)bis[N′-(4,4-diethoxybutyl)urea] with Resorcinol and Its Derivatives

An efficient procedure has been developed for the synthesis of macroheterocycles by acid-catalyzed reaction of N,N′-(1,4-phenylene)bis[N′-(4,4-diethoxybutyl)urea] with resorcinol, 2-methylresorcinol, and pyrogallol. The structure of the isolated compounds was proved by spectral methods.

     

Structure of N,N-disubstituted α,β-unsaturated α-amino aldehydes

Study of the IR and¹H and¹³C NMR spectra of N,N-disubstituted ,-unsaturated -amino aldehydes showed that in the nature of the electron density distribution these compounds occupy an intermediate position between -unsubstituted amino olefins and ,-unsubstituted aldehydes, being significantly closer to the latter.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2031–2034, September, 1991.     

Reaction of 9-amino(phenylamino)methylene- and 9-α-aminobenzylidene-4-azafluorenes with some electrophilic reagents

It was shown that initial protonation of 9-aminomethylene-4-azafluorene takes place at the pyridine nitrogen atom. In nitrosation of this azafluorene, 4-azafluorenone oxime is formed, and in reaction with dichlorocarbene, 1-amino-2, 2'-dichlorospiro[4-azafluorene-9,3-cyclopropane] is formed. Acylation yields mono- or diacyl derivatives as a function of the acylating agent and reaction conditions.Russian University of National Friendship, Moscow 117923. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 527–533, April, 1995. March 14, 1995.     

Reaction of α-(trialkylstannyl) acetylenes with metallic sodium

-Trialkylstannylacetylenes react under mild conditions with metallic sodium at the Sn-C(sp) bond to give hexaalkyldistannanes and sodium acetylalkynides inca. 65–85 % yields.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1109–1110, June, 1994.     

Reaction of N′-(Arylmethylidene)-2-oxo-2H-chromene-3-carbohydrazides with Methyl 1-Bromocycloalkanecarboxylates and Zinc

Russian Journal of General Chemistry - Depending on the ring size in the Reformatsky reagent and the nature of substituents in arylmethylidene fragment, the reactions of Reformatsky reagents...     

Reaction of dibenzylphosphine oxide with α,β-unsaturated O-methyloximes

The reaction of dibenzylphosphine oxide with O-methyloximes of some ,-unsaturated ketones results in the phosphorylation at the -carbon atom to form methoxyiminophosphine oxides, whereas the reaction of dibenzylphosphine oxide with O-methyloximes of ,-unsaturated aldehydes affords aminodihydrophosphole oxides.     

Lipase-catalyzed kinetic resolution approach toward enantiomerically enriched 1-(β-hydroxypropyl)indoles

In a route towards enantiomerically enriched 1-(β-hydroxypropyl)indoles, which are potentially useful building blocks for high value-added chemicals synthesis, a kinetic resolution approach by means of lipase-catalyzed enantioselective acylation as well as hydrolysis/methanolysis has been elaborated for the first time. The enzymatic resolution of chiral N-substituted indole-based sec-alcohols was successfully accomplished, yielding both enantiomeric forms of the employed derivatives with up to >99% enantiomeric purity via an enantioselective transesterification under mild reaction conditions. The most selective resolutions were obtained using fungal (CAL-B and TLL) and bacterial (PFL and BCL) lipases and vinyl acetate as the acyl?group donor. The synthetic protocol described herein is very simple, user-friendly and efficient, thus paving the way for future access towards more complex compounds of this type. The absolute configurations of novel enantiomeric derivatives, and thus stereoselectivity of the described enzymatic reactions were confirmed by application of CDA-based NMR methodology and single-crystal X-ray diffraction analysis.