Synthesis,X-ray structure,and stevens rearrangement of 1,1-di(prop-2-yn-1-yl)-2,5-dihydro-1H-pyrrol-1-ium bromide

1,1-Di(prop-2-yn-1-yl)-2,5-dihydro-1H-Pyrrol-1-ium bromide was obtained with interaction of 3-pyrroline with propargyl bromide and its structure was studied by X-ray analysis. It has been shown that the Stevens rearrangement of obtaining salt leads to the formation of 1-(hexa-4,5-dien-1-yn-3-yl)-2,5-dihydro-1H-pyrrol.     

Convenient,DBU-promoted anti-Markovnikov hydration of 2-methyl-1-(3-arylprop-2-yn-1-yl)-1H-imidazoles in wet NMP

During attempts to involve 5-methyl-2-phenyl-1-(3-phenyl-prop-2-yn-1-yl)-1H-imidazole in a base-promoted, allene-mediated cyclization of the alkyne moiety onto the nearby aromatic ring, substantial amount of the ketone resulting from hydration of the alkyne with adventitious water was discovered. The formation of the ketone of the anti-Markovnikov alkyne hydration was developed into a preparative method. This method, alternative to the common acid-and metal-catalyzed approaches, may be of particular utility when alkyne hydration needs to be performed in the presence of acid-labile groups.     

Synthesis of [3-(trimethylsilyl)prop-2-yn-1-yl] selenides

Efficient and selective methods have been developed for the synthesis of previously unknown organyl [3-(trimethylsilyl)prop-2-yn-1-yl] selenides, organyl prop-2-yn-1-yl selenides, and bis[3-(trimethylsilyl) prop-2-yn-1-yl] selenide by reactions of 3-bromo-1-(trimethylsilyl)prop-1-yne with the corresponding organylselenolates and sodium selenide generated from diorganyl diselenides or elemental selenium by the action of sodium tetrahydridoborate.     

Stevens rearrangement of heterocyclic ammonium salts containing prop-2-yn-1-yl group

Stevens rearrangement was studied of ammonium salts where piperidinium or morpholinium groups are linked to prop-2-yn-1-yl moiety and labile hydrogen atom functions (methoxycarbonylmethyl, phenacyl, cyanomethyl). In the case of phenacyl analog furan derivatives were formed, in other cases dienamines were the reaction products.     

Rh(I)-catalyzed cyclization of 1-arylprop-2-yn-1-ol derivatives utilizing rhodium 1,4-migration

A highly useful method for the construction of cyclopentanone derivatives fused with aromatic ring based on hydrorhodation-1,4-rhodium migration sequence is achieved. Treatment of 1-aryl-prop-2-yn-1-ols, which are easily accessible via an addition of acetylides to the corresponding aryl aldehydes, with a catalytic amount of [Rh(cod)2]2(BF4) and P(p-tolyl)3 in the presence of a base gives cyclopentanone derivatives in moderate to good yield.     

Base-Catalyzed Intramolecular Cycloaddition of Dialkyl(4-hydroxybut-2-yn-1-yl)[3-(4-bromophenyl)prop-2-yn-1-yl]ammonuim Chlorides and Recyclization of the Products

Russian Journal of Organic Chemistry - Dialkyl(4-hydroxybut-2-yn-1-yl)[3-(4-bromophenyl)prop-2-yn-1-yl]ammonium chlorides in the presence of 2 equiv of potassium hydroxide at room temperature...     

Ensembles of rings with a coumarin unit 1. Synthesis of 3-(2-R-thiazol-4-yl)-and 3-(4-R-thiazol-2-yl)coumarins

We have synthesized 3-(2-R-thiazol-4-yl)coumarins (R=H, CH₃, CH₂CN, Ar) by condensation of 3-(-bromoacetyl)coumarins with thioamides. We obtained 3-(4-R-thiazol-2-yl)coumarins (R=H, Ar) by several methods. By reaction of 2-cyanomethyl-4-phenylthiazole with 2-hydroxybenzaldehydes, we synthesized 2-imino-3-(4-phenylthiazol-2-yl)coumarins, which were converted to the corresponding coumarins by acid hydrolysis. For 3-(2-R-thiazol-4-yl)coumarins (R=CH₂CN), we carried out reactions with aromatic aldehydes. We propose alternative methods for synthesis of 2-[2-aryl(hetaryl)-1-cyanoethenyl]-4-(coumarin-3-yl)thiazoles.Ukrainian Pharmaceutical Academy, Kharkov 310002. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1345–1355, October, 1997.     

Sonogashira reaction of 5-substituted 3-(prop-2-yn-1-yl)oxolan-2-ones

Palladium-catalyzed cross-coupling of 5-methyl- and 5,5-dimethyl-3-(prop-2-yn-1-yl)oxolan-2-ones with dihaloarenes (dihaloheteroarenes) gave mixtures of the corresponding mono- and bis-coupling products. The latter can be obtained as the major products by variation of the catalytic system.     

Synthesis of 2-and 6-chloro-3-(5-methyl-1,3,4-oxadiazol-2-yl)pyridines

A convenient synthesis of 2- and 6-chloro-3-(5-methyl-1,3,4-oxadiazol-2-yl)pyridines, 3 and 10 , utilizing the readily available amide 7 is described. Incorporation of the 3-t-butylamino-2-hydroxypropoxy side chain onto 3 provided 2 , a potential bioisostere of 1 . The antihypertensive activities of 2 and 12 were evaluated in the spontaneously hypertensive rat model.     

Synthesis of 2-hetaryl-3-(indol-1-yl)-and -(3-pyrrol-1-yl)maleimides and study of their conversions under the action of protic acids*

A series of 3-(indol-1-yl)maleimides has been synthesized, substituted at position 2 by residues of amines or various nitrogenous heterocycles. The possibility of obtaining new polycondensed heterocyclic structures from them has been studied. Experimental investigations confirmed theoretical predictions made on the basis of results of quantum-chemical calculations.     

Synthesis of 2-and 5-(1,1-Dimethyl-1,2,5,6-tetrahydropyridinium-3-yl)oxadiazoline Iodides

ＩｎｔｒｏｄｕｃｔｉｏｎＲｅｃｅｎｔｌｙ ,ｔｈｅｉｎｃｒｅａｓｉｎｇｄｅｍａｎｄｆｏｒｅｆｆｅｃｔｉｖｅｔｒｅａｔ ｍｅｎｔｏｆｎｅｕｒｏｄｅｇｅｎｅｒａｔｉｖｅｄｉｓｅａｓｅｓ ,ｐａｒｔｉｃｕｌａｒｌｙＡｌｚｈｅ ｉｍｅｒ’ｓｄｉｓｅａｓｅ (ＡＤ) ,ｉｓｂｅｃｏｍｉｎｇｍｏｒｅａｎｄｍｏｒｅｕｒ ｇｅｎｔ.ＡｍｏｎｇｔｈｅｒｅｓｅａｒｃｈｅｓｉｎｔｈｅｒａｐｅｕｔｉｃｓｆｏｒＡＤ ,ｍａｎｙｍｕｓｃａｒｉｎｉｃｃｏｍｐｕｎｄｓｎｏｔｏｎｌｙａｒｅｂｅｎｅｆｉｃｉａｌｉｎｔｈｅｔｒｅａｔ ｍｅｎｔｏｆＡ…     

1-(2-炔丙基)-7,8-二氢喹啉-2,5(1H,6H)-二酮的合成

以1,3-环己二酮为原料,依次经亚胺化反应、Michael加成-环化反应、烷基化反应合成了含有端基炔的喹啉酮衍生物——1-(2-炔丙基)-7,8-二氢喹啉-2,5(1H,6H)-二酮,其结构经1H NMR,HR-MS和2D NMR确证。     

Synthesis and in-vitro antitumor activity of 1-[3-(indol-1-yl)prop-1-yn-1-yl]phthalazines and related compounds

A series of novel 3-(indol-1-yl)prop-1-yn-1-yl-substituted phthalazines and related azines was prepared via a concise pathway by palladium-catalyzed cross-coupling of appropriate halo-azines and N-propargylindoles. Some of the compounds exhibited significant antitumor activity in an in-vitro assay.     

Chemistry of hetero analogs of isoflavones 26. Synthesis of 2-alkyl derivatives of 3-(thiazol-2-yl)-and 3-(benzothiazol-2-yl)chromones

Treatment of substituted 2-(2,4-dihydroxyphenacyl)thiazole and 2-(2,4-dihydroxyphenacyl)benzothiazole with propionic and isobutyric anhydrides gives the substituted 2-ethyl-and 2-isopropyl-7-acyloxychromones. The use of pivaloyl chloride gives 1-pivaloyloxy-2-hetarylstyrene derivatives. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 835–840, June, 2008.     

Synthesis of 3-[5-(biphenyl-4-yl)pyrrol-2-yl]-1-phenylprop-2-yn-1-ones by palladium-free cross-coupling between pyrroles and haloalkynes on aluminum oxide

Cross-coupling of 2-(biphenyl-4-yl)pyrroles derived from 1-(biphenyl-4-yl)ethanone oximes and acetylene with 3-bromo-1-phenylprop-2-yn-1-one on aluminum oxide gave 3-[5-(biphe-nyl-4-yl)pyrrol-2-yl]-1-phenylprop-2-yn-1-ones in 35–46% yields.     

Claisen重排反应合成5-烯丙基-4-羟基异吲哚啉-2-羧酸叔丁酯

以2,3-二甲基苯酚(2)和烯丙基溴为原料,经过醚化、溴代、关环及Claisen重排等四步反应,合成得到5-烯丙基-4-羟基异吲哚啉-2-羧酸叔丁酯(1),4步反应总收率为17.8％.中间体及产物结构经1 H NMR和ESI-MS表征,产物结构进一步经过FT-IR、13 C NMR及X-射线单晶衍射进行确认.同时,重点...