共查询到20条相似文献,搜索用时 15 毫秒
1.
Matthias D'hooghe 《Tetrahedron》2004,60(16):3637-3641
The reactivity of 1-arenesulfonyl-2-(bromomethyl)aziridines with respect to lithium dialkylcyanocuprates and lithium dialkylcuprates (Gilman reagents) has been evaluated for the first time, pointing to the conclusion that these substrates can be applied successfully as synthetic equivalents for the 2-aminopropane dication synthon towards 2-alkylaziridines and α-branched N-tosylamides in good yields. 相似文献
2.
Matthias D'hooghe 《Tetrahedron》2006,62(10):2295-2303
1-Arylmethyl-2-(bromomethyl)azirdines were converted into the corresponding 2-(aryloxymethyl)aziridines upon treatment with the appropriate potassium phenoxides in DMF/acetone in excellent yields, followed by regioselective ring opening towards N,N-di(arylmethyl)-N-(2-bromo-3-aryloxypropyl)amines using benzyl bromide in acetonitrile. Treatment of the latter β-bromoamines with sodium methoxide afforded the desired 2-amino-1-aryloxy-3-methoxypropanes as the major compounds (49-58%) besides the isomeric 3-amino-1-aryloxy-2-methoxypropanes in minor quantities (9-15%). 相似文献
3.
Matthias D'hooghe 《Tetrahedron》2008,64(6):1064-1070
1-Arylmethyl-2-(bromomethyl)aziridines were transformed into 2-[N-(arylmethyl)amino]pentanedinitriles upon treatment with an excess of potassium cyanide in DMSO through an unprecedented and peculiar reaction mechanism, involving base-induced ring opening of intermediate 2-(cyanomethyl)aziridines into allylamines, followed by migration of the double bond out of the conjugation towards aldimines via enamine intermediates. The resulting aminopentanedinitriles served as substrates for the synthesis of novel 2-imino-5-methoxypyrrolidines upon treatment with sodium methoxide in methanol, which were either acetylated at the free imino group to afford the more stable N-acetylimino derivatives or hydrolyzed towards the corresponding synthetically relevant 5-methoxypyrrolidin-2-ones. 相似文献
4.
Matthias D'hooghe 《Tetrahedron》2005,61(36):8746-8751
1,3-Heteroatom substituted 2-aminopropane derivatives have been prepared from 2-(bromomethyl)-1-sulfonylaziridines for the first time using sodium azide or different potassium phenoxides in water in the presence of silica gel. The applicability of 1-arenesulfonyl-2-(bromomethyl)aziridines for the synthesis of functionalized sulfonamides has also been demonstrated towards different 1,3-dialkoxy-2-(tosylamino)propanes and 1,3-dialkylthio-2-(tosylamino)propanes upon treatment with the appropriate sodium alkoxide or sodium alkylthiolate in the corresponding alcohol or in methanol, respectively. 相似文献
5.
Treatment of 1-benzyl-2-(bromomethyl)aziridine, and some aryl substituted analogues, with an excess of iodomethane resulted in N-allyl-N-benzyl-N,N-dimethylammonium salts, in good yields. These quaternary allylammonium salts are of importance in different fields, from organic synthesis and polymeric chemistry to agricultural use. 相似文献
6.
D'hooghe M Van Speybroeck V Van Nieuwenhove A Waroquier M De Kimpe N 《The Journal of organic chemistry》2007,72(13):4733-4740
1-Arylmethyl-2-(cyanomethyl)aziridines were transformed into 4-(N,N-bis(arylmethyl)amino)-3-(pyrrolidin-1-yl)butanenitriles and 4-(N,N-bis(arylmethyl)amino)-2-butenenitriles via 4-(N,N-bis(arylmethyl)amino)-3-bromobutanenitriles in high yields and purity. The key steps involve the unprecedented regiospecific ring opening of intermediate 2-(cyanomethyl)aziridinium salts by bromide and pyrrolidine in acetonitrile, exclusively at the substituted aziridine carbon atom. The results were rationalized on the basis of ab initio calculations. 相似文献
7.
Good nucleophilicity of the ring nitrogen in chiral (2R,1′R)-2-acyl-(1′-phenylethyl)aziridines initiated the reaction with various acid chlorides to form the corresponding acylaziridinium ion intermediates whose rings were opened by the chloride anion to yield the β-amino-α-chlorocarbonyl compounds. The subsequent displacement of the chloride with the internal oxygen nucleophile originated from methylchloroformate, acetyl chloride, and methyl chlorooxoacetate yielded oxazolidin-2-ones, β-amino-α-acetyloxypropionates, and morpholin-2,3-diones, respectively. 相似文献
8.
Nicolas Lebegue Gaetan Charrier Pascal Carato Saïd Yous Pascal Berthelot 《Tetrahedron letters》2004,45(52):9509-9511
The decarbalkoxylations of disubstituted geminal diesters by water–DMSO with added salts (KCN or NaCN) is a convenient preparative route leading to the corresponding monoesters. Herein, we described an efficient and very simple methodology for the preparation of 2-(ethylsulfanyl)aniline derivatives through the unexpected ring opening of the corresponding N-substituted-2(3H)-benzothiazolones in the presence of disubstituted geminal diester, KCN, and water–DMSO. 相似文献
9.
A short synthesis of alkyl 2-(bromomethyl)aziridine-2-carboxylates and alkyl 3-bromoazetidine-3-carboxylates was developed involving amination, bromination, and base-induced cyclization of alkyl 2-(bromomethyl)acrylates. These new small ring azaheterocyclic α- and β-amino acid derivatives are promising synthons as demonstrated by their transformation to 2-(aminomethyl)aziridine-2-carboxylates and 3-aminoazetidine-3-carboxylates. 相似文献
10.
A one-step approach to the biologically interesting 3-aminoazetidines is described. The reaction concerns a ring transformation of 1-arylsulfonyl-2-(halomethyl)aziridines with aliphatic amines under various reaction conditions. 相似文献
11.
An efficient and convenient approach for the preparation of functionalized 2-(methylsulfonyl)pyrimidine derivatives has been developed through cyclic condensation of malonate derivatives with S-methylisothiouronium sulfate followed by derivation and oxidation in water–acetone mixture using oxone as the oxidant. This synthetic strategy provides an efficient and environmentally friendly approach for easy access to 2-(methylsulfonyl)pyrimidine derivatives with considerable yields. 相似文献
12.
新手性源5-(l-孟氧基)-3-溴-2(5H)-呋喃酮的合成和结构 总被引:7,自引:0,他引:7
文中深入研究了5-(l-孟氧基)-3-溴-2(5H)-呋喃酮新手性源(5a)的合成方法及其不对称合成反应。5a不仅制备方法简便,光学纯度单一,而且它作为稳定的Michael受体,可与碳、氧、氮、硫等不同的亲核试剂发生串联的Michael加成/分子内亲核取代反应,制备得到含有多个手性中心的双环[3.3.0^3^,^7]-5-辛烯类化合物、双环[3.1.0^3^,^5]-己烷类化合物和螺-环丙烷类化合物。本文报道了该手性呋喃酮5a的合成和构型测定。 相似文献
13.
An efficient base catalyzed one pot multicomponent reaction of aryl/hetryl chalcones, thiosemicarbazide and 1-(benzofuran-2-yl)-2-bromoethan-1-one was developed to synthesize the novel 4-(benzofuran-2-yl)-2-(3-(aryl/heteryl)-5-(aryl/heteryl)-4,5-dihydro-1H-pyrazol-1yl)thiazole derivatives. 相似文献
14.
Kiril B. Gavazov Vanya D. Lekova Atanas N. Dimitrov Georgi I. Patronov 《Central European Journal of Chemistry》2007,5(1):257-270
The formation and extraction of ion-associate complexes between the vanadium(V)-4-(2-thiazolylazo)resorcinol (TAR) anionic
chelate and the cations of some mono-and ditetrazolium salts {3-(4,5-dimethyl-2-thiazol)-2,5-diphenyl-2H-tetrazolium bromide
(Thiazolyl blue, MTT), 3-(2-naphtyl)-2,5-diphenyl-2H-tetrazolium chloride (Tetrazolium violet), 2-(4-iodophenyl)-3-(4-nitrophenyl)-5-phenyl-2H-tetrazolium
chloride (Iodonitrotetrazolium chloride), 3,3′-[3,3′-dimetoxy(1,1′-biphenyl)-4,4′-diyl]-bis[2,5-diphenyl-2H-tetrazolium] chloride
(Tetrazolium blue chloride) and 3,3′-(3,3′-dimetoxy-4,4′-biphenylene)bis[2-(4-nitrophenyl)-5-phenyl-2H-tetrazolium chloride]
(Nitro blue tetrazolium chloride)} have been studied. The optimum extraction conditions have been found. The composition of
the V-TAR-monotetrazolium and V-TAR-ditetrazolium complexes extracted into chloroform has been determined to be 1:2:3 and
2:4:3 respectively. The extraction, distribution and association constants, and the recovery factors have been calculated.
The relationship between the molecular weight of tetrazolium cations, and the association constants of their complexes has
been discussed. The special behavior of the tetrazolium cations, containing-NO2 groups has been noticed. The effects of foreign ions and reagents on the extraction of vanadium with TAR and the best tetrazolium
salt-MTT have been studied. A sensitive, selective, simple and fast method for the determination of vanadium has been developed.
相似文献
15.
Marcus M. Sá Luciano Fernandes Misael Ferreira Adailton J. Bortoluzzi 《Tetrahedron letters》2008,49(7):1228-1232
Allylic thiocyanates and novel heterocycles containing the 1,3-thiazin-4-one core are easily obtained in high yields and mild conditions by nucleophilic displacement of 2-(bromomethyl)alkenoates (derived from Morita-Baylis-Hillman adducts) with sulphur-centred nucleophiles in aqueous acetone at 25 °C. Treatment of allylic bromides with NaSCN gave the corresponding (Z)-2-(thiocyanomethyl)alkenoates, while the reaction with thiourea followed by a basic work-up selectively produced (5Z)-2-amino-5-arylidene-1,3-thiazin-4-ones. The structural assignments were confirmed by X-ray diffraction analysis. 相似文献
16.
I. A. Novakov B. S. Orlinson R. V. Brunilin M. B. Nawrozkij E. N. Savel’ev G. A. Novikova 《Chemistry of Heterocyclic Compounds》2006,42(10):1331-1333
A method has been developed for the synthesis of N2-adamantyl-2-amino-6-methyl-4(3H)-pyrimidinones based on the reaction of (adamant-1-yl)alkylamine with 2-(ethylsulfanyl)-6-methyl-4(3H)-pyrimidinone
which can lead to the corresponding derivatives in which the exocyclic nitrogen atom and the adamantyl radical are separated
by a hydrocarbon fragment.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1541–1544, October, 2006. 相似文献
17.
A series of medicinally important 2-amino-4-(nitromethyl)-4H-chromene-3-carbonitriles were synthesized using enantioselective conjugate addition of nitromethane to 2-iminochromenes. The reactions were performed using L8-Cu (II) catalytic system and moderate to good enantioselectivities (62–88%) and yields (66–96%) were obtained. 相似文献
18.
Aïcha Arfaoui 《Tetrahedron》2009,65(25):4904-4907
A regioselective coupling of ethyl 2-(bromomethyl)-3-cyanoacrylate and primary amines is described to give ethyl 2-[(alkylamino)(cyano)methyl] acrylates in good yields. Whereas the conversion of allyl bromide in the presence of TEAF leads to the first synthesis of ethyl 3-cyano-2-(hydroxymethyl) acrylate. 相似文献
19.
Yu. M. Volovenko T. A. Volovnenko A. V. Dobrydnev 《Chemistry of Heterocyclic Compounds》2006,42(9):1137-1142
3-Cyano-3-hetaryl-2-oxopropyl-and 3-cyano-3-hetaryl-1-methyl-2-oxopropyl ethanethioates were obtained by the acylation of
2-azahetarylacetonitriles with (acetylthio)acetyl and α-(acetylthio)propionyl chlorides respectively. They are deacetylated
by the action of amines and undergo cyclization with the formation of 5-amino-4-hetarylthiophen-2(2H)-ones.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1314–1319, September, 2006. 相似文献