Novel N-aryl and N-heteroaryl sulfamide synthesis via palladium cross coupling

A novel and efficient synthesis of N-aryl and N-heteroaryl sulfamides via an intermolecular palladium-catalyzed coupling process has been developed. The reactions proceeded with good to excellent yields and were tolerant of a wide range of functional groups. [reaction: see text]     

Synthesis of thiophene derivatives via palladium-catalyzed coupling reactions

Thiophene derivatives with multiple substitutions are prepared from vinylidene bromide, which is synthesized by the reaction of thiophene-2-carboxaldehyde with carbon tetrabromide in the presence of PPh₃, as a core molecule through several coupling reactions such as Suzuki-Miyaura coupling and palladium-catalyzed CH arylation. The reactions with a wide variety of organic halides lead to a series of substituted thiophene derivatives in moderate to good yields.     

Synthesis of N-aryl derivatives of vicinal aminoalcohols

Synthesis was performed of substituted 2-propanols based on glycidyl phenyl and glycidyl allyl ethers, Also some acetic acid esters were prepared.     

Nickel-catalyzed C-N crossing coupling reaction: The synthetic method for N-aryl substituted indenoindole

A nickel-based catalyst was employed for the first time in the crossing-coupling of indenoindoles with bromo-/iodoarenes. A simple and practical method was provided for the synthesis of N-aryl substituted indenoindole and the mechanism of this reaction was discussed.     

Functional derivatives of thiophene

A method is proposed for the synthesis of isatin analogs — 4,5-dioxothieno[2,3-b] pyrroles and 5,6-dioxothieno[3,2-b]pyrroles — by reaction of oxalyl chloride with amino-substituted α-amino- and Β-aminothiophene. The thiosemicarbazones of 4-ary1-5,6-dioxothieno[3,2-b]pyrroles were synthesized. n]mis|See [1] for communication X.     

Functional derivatives of thiophene

2-Aryl-4-oxothieno[2,3-d]oxazine derivatives were synthesized. Opening of the oxazine ring to give 2-benzamidothiophene-3-carboxylic acid hydrazide derivatives is observed when these compounds are treated with hydrazine hydrate.See [1] for Communication 17.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 45–46, January, 1980.     

Organodimagnesium derivatives of thiophene

It was established that 2,5-dibromo-3-R-4-arylthiophenes form organodimagnesium compounds in ether with the accompaniment of dibromoethane. It is shown that because of steric hindrance, only 2-ethoxalyl-3-R-4-arylthiophenes are formed in the reaction of the organodimagnesium compounds with diethyl oxalate. It was established that the bromomagnesiumethoxycarbinolates obtained from the indicated thiophenes and bromomagnesium ethoxide have high thermal stabilities. The IR and PMR Spectra of the synthesized compounds were studied.See [1] for Communication 3.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 754–757, June, 1982.     

Functional derivatives of thiophene

5-Tosylamino-2,3-dialkylthiophenes, which are alkylated to the corresponding 5-alkyl (tosyl)-amino derivatives, were synthesized from 2-amino-3-carbethoxy-4,5-dialkylthiophenes by tosylation and subsequent decarboxylation.See [1] for communication XV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 204–206, February, 1977.     

Functional derivatives of thiophene

Acyl derivatives of substituted β-thienylhydrazines were obtained by reaction of 2-methyl-3-carbethoxy-4-hydroxythiophene with acyl hydrazines. Hydrolysis of the products gave a thienylhydrazine derivative and its hydrochloride.     

Functional derivatives of thiophene

A preparative method for the synthesis of thienobenzothiazines — phenothiazine analogs-was worked out on the basis of 2-methyl-3-carbethoxythiophene derivatives and nitroarenesulfenyl chlorides.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 741–745, June, 1973.     

Functional derivatives of thiophene

The derivatives obtained by reaction of o-halonitrothiophenes with cyanoacetic and acetoacetic esters were converted to thieno[2,3-b]- and thieno[3,2-b]pyrroles by reductive cyclization.See [1] for communication VI.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1628–1630, December, 1973.     

Functional derivatives of thiophene

A method is proposed for the synthesis of 5-acylamino-2,3-dimethylthiophene-4-carbaldehydes and 5-acylamino-2,3-tetramethylenethiophene-4-carbaldehydes by the formylation of the corresponding thiophenes using the Vilsmeier reaction. From the formyl derivatives obtained, previously unaccessible derivatives of thieno[2,3-b]pyridine, thieno[2,3-d]pyrimidine, and thieno[3′,2′∶5,6]pyrido[2,3-d]-pyrimidine have been synthesized.     

Functional derivatives of thiophene

The nitration of 3-ethoxycarbonyl-4-hydroxy-2-methyl- and 4-chloro-3-ethoxycarbonyl-2-methylthiophenes has given the corresponding 5-nitro derivatives of thiophene. The 4-chloro-3-ethoxycarbonyl-2-methylthiophene was synthesized by the decarboxylation of 3-chloro-4-ethoxycarbonyl-5-methylthiophene-2-carboxylic acid, which is formed by the oxidation of 3-chloro-4-ethoxycarbonyl-5-methylthiophene-2-carbaldehyde.For Communication IV, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1024–1025, August, 1973.     

Novel,highly polarizable thiophene derivatives for use in nonlinear optical applications

The synthesis of a variety of thiophene-containing materials for use in electro-optic devices requiring highly birefringent materials is reported. The refractive indices were measured with the use of an Abbé refractometer, and from these results the optical anisotropies, polarizabilities and order parameters were determined. The replacement of a phenyl ring by thiophene leads to large enhancements of polarizability. The most significant increases in polarizability anisotropy were observed when the rigid core was a collinear 5,5′-disubstituted-2,2′-dithienyl unit. The changes in the optical properties are discussed in terms of the structural units (thiophene, phenyl, isothiocyanate, nitrile, butylsulfanyl, alkoxy and alkyl moieties) used and their positions with respect to the molecular core.     

Synthesis of some thiophene derivatives

The synthesis of thiopene derivatives from diacetylenic hydrocarbons has been described [1]. We have examined for the first time the reaction of diacetylenic diesters with hydrogen sulfide and with NaHS. The diacetylenic diesters react readily with hydrogen sulfide or NaHS in acetone at pH 9–10 to give 2,5-disubstituted thiopheries (see Table 1).Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 5, pp. 713–714, May, 1970.     

新型N-芳基哌嗪取代苯并呋喃衍生物的合成

以5-二甲氨基水杨醛和2-溴-4'-氟苯乙酮为原料,经缩合和取代反应制得中间体6-二乙氨基-2-[4'-(N-哌嗪基)苯甲酰基]苯并呋喃(2);2与卤代烃反应合成了6个新型的N-芳基哌嗪取代苯并呋喃衍生物(4a~4f),收率76%~93%,其结构经1H NMR,13C NMR和HR-MS(ESI-TOF)表征。     

低价钛引起的羧酸衍生物与芳酮的还原偶联反应

本文报道了在低价钛试剂作用下羧酸衍生物与芳酮的还原偶联反应.     

Coloured products from thiophene and aromatic 1,2-diketones

Thiophene and phenanthrene-9,10-quinone react in acidic solution to produce the deep blue extended quinone (Z,Z)-2,5-di(9-oxo-9,10-dihydro-10-phenanthrylidene)-2,5-dihydrothiophene the structure of which is confirmed by X-ray crystallography. Other aromatic 1,2-diketones give rise to related products.