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1.
The synthesis of the isomeric 6(5)-phenyl-5(6)-pyridyl-2,3-dihydroimidazo[2,1-b]thiazoles are described. Only the synthesis of 5-phenyl-6-(2-pyridyl)-2,3-dihydroimidazo[2,1-b]thiazole failed. 相似文献
2.
Susan Shilcrat Ivan Lantos Michael Mcguire Lendon Pridgen Louisa Davis Drake Eggleston David Staiger Lee Webb 《Journal of heterocyclic chemistry》1993,30(6):1663-1671
The ethyl chloroformate salts of a variety of benzo-fused six membered π-deficient heteroaromatics, including quinoline, isoquinoline, 4-chloroquinoline, 3-bromoquinoline, phthalazine, and quinazoline, reacted with 6-aryl-2,3-dihydroimidazo[2,1-b]thiazole at the 5-position. The dihydroheteroaromatic adducts were oxidized by o-chloranil, sulfur, or electrochemical methodology to form the 5-heteroaromatic-6-aryl-2,3-dihydroimidazo[2,1-b]thiazoles, 10-15 . In each example, the regiochemistry of addition to the heteroaromatic ring was established. 相似文献
3.
V. M. Dianov 《Russian Journal of Organic Chemistry》2006,42(7):1028-1030
The reaction of dihydroimidazole-2-thiol with N-(3-chloro-2-oxopropyl)phthalimide gave 2-[3-(4,5-dihydroimidazol-2-ylsulfanyl)-2-oxopropyl]-1,3-dioxo-1H-isoindole which underwent intramolecular heterocyclization to dihydroimidazothiazole system by the action of a dehydrating agent. Treatment of 3-(1,3-dioxo-1H-isoindol-2-ylmethyl)-5,6-dihydroimidazo[2,1-b]thiazole with concentrated hydrochloric acid led to the formation of dihydroimidazo[2,1-b]thiazol-3-ylmethanamine. Water-soluble quaternary 3-(1,3-dioxo-1H-isoindol-2-ylmethyl)-5,6-dihydroimidazo[2,1-b]thiazolium salts were obtained by alkylation of 3-(1,3-dioxo-1H-isoindol-2-ylmethyl)-5,6-dihydroimidazo[2,1-b]thiazole with alkyl halides. 相似文献
4.
E. Suloeva M. Yure E. Gudriniece S. Belyakov M. Petrova I. Kalnite 《Chemistry of Heterocyclic Compounds》2001,37(3):329-337
Syntheses are reported for a series of 2-alkylamino-6-phenyl-4-trifluoromethylpyridines. The reaction of 3-cyano-2-(hydroxyalkylamino)-6-phenyl-4-trifluoromethylpyridines with thionyl chloride gave the corresponding 2-(chloroalkylamino)pyridines, 8-cyano-5-phenyl-7-trifluoromethyl-2,3-dihydro-imidazo[1,2-a]pyridines, and 9-cyano-6-phenyl-8-trifluoromethyl-2,3,4-trihydropyrido[1,2-a]-pyrimidines. X-ray diffraction structural analysis was used to study 8-cyano-5-phenyl-7-trifluoromethyl-2,3-dihydroimidazo[1,2-a]pyridine. 相似文献
5.
Wenjie Liu Yuzhen Chen Yanling Huang Ziying Li Anda Wang 《Phosphorus, sulfur, and silicon and the related elements》2016,191(5):689-692
A novel and facile method for the direct sulfenylation of 2,3-dihydroimidazo[2,1-b]thiazoles with disulfides has been developed. The transformation is promoted by iodine under metal-free conditions, providing the corresponding products in moderate to good yields. 相似文献
6.
The reaction of 2-amino-4-methyl-6-(2-pyridyl)-7,8-dihydroindazolo[4,5-d]thiazole, obtained by treating 3-methyl-4-oxo-1-(2-pyridyl)-4,5,6,7-tetrahydroindazole with pyridinium bromide perbromide and then with thiourea, and 2-amino-4-methyl-6-phenyl-7,8-dihydroindazolo[4,5-d]thiazole with 4-bromo-, 4-fluoro-, 4-dimethylamino-, 4-methoxy-, 3,4-dimethoxy-, and 3,4-methylenedioxybenzaldehydes, furfural, pyridinecarbaldehyde, and thiophenecarbaldehyde gave the corresponding Schiff bases. The products of the condensation of these aminothiazoles with cinnamaldehyde, 1-(2-pyridyl)- and 4-chloro-1-(2,4-difluorophenyl)-5-formyl-3-methyl-6,7-dihydroindazoles, 2-formyl-dimedone, and 2-formyl-1,3-indanedione were also obtained. 相似文献
7.
J. Suloeva M. Jure E. Gudriniece M. Petrova A. Kemme 《Chemistry of Heterocyclic Compounds》2002,38(6):714-729
The alkylation, acylation, halogenation, nitration, oxidation, and hydrolysis reactions of 8-cyano-5-phenyl-7-trifluoromethyl-2,3-dihydroimidazo[1,2-a]pyridine have been studied. It was found that the 6-halo derivatives add alcohol to give covalent solvates. X-ray analysis has been carried out on one of the solvates (6-chloro-8-cyano-7-ethoxy-5-phenyl-7-trifluoromethyl-1,2,3,7-tetrahydroimidazo[1,2-a]pyridine) as well as on 8-cyano-5-phenyl-7-trifluoromethyl-2,3-dihydroimidazo[1,2-a]pyridine trifluoroacetate. 相似文献
8.
Nuray Ulusoy Muammer Kiraz Ömer Küçükbasmacı 《Monatshefte für Chemie / Chemical Monthly》2002,133(10):1305-1315
Summary. New 4-alkyl/aryl-1-((6-(4-bromophenyl)-imidazo[2,1-b]thiazol-3-yl)-acetyl)-3-thiosemicarbazides and 3-alkyl/aryl-2-(((6-(4-bromophenyl)-imidazo[2,1-b]thiazol-3-yl)-acetyl)-hydrazono)-4-thiazolidinones were synthesized from 6-(4-bromophenyl)-imidazo[2,1-b]thiazole-3-acetic acid hydrazide. Their structures were elucidated by elemental analyses and spectroscopic data. All compounds
were tested for antibacterial and antifungal activities. The antimicrobial activities of the compounds were assessed by the
microbroth dilution technique. The compounds were also evaluated for antituberculosis activity against Mycobacterium tuberculosis H37Rv (ATCC 27294); they exhibited varying degrees of inhibition in the in vitro primary screening at 6.25 μg · cm−3. The most active compound was 3-(4-nitrophenyl)-2-(((6-(4-bromophenyl)-imidazo[2,1-b]thiazol-3-yl)-acetyl)-hydrazono)-4-thiazolidinone.
Corresponding author. E-mail: nurayulusoy@yahoo.com
Received December 10, 2001. Accepted (revised) March 1, 2002 相似文献
9.
Ethyl (6-phenyl-5,6-dihydroimidazo[2,1-b]thiazol-3-yl) acetate hydrobromide shows an allylic transposition in alkaline medium and gives ethyl (6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazol-3-ylidene)acetate. This compound possesses an exocyclic double bond which is stable upon acidification. The intermediate ethyl (2-imino-3-alkylthiazolin-4-yl)-acetates undergo an analogous transposition upon treatment with base, which is reversible upon acidification. These transpositions were observed in the pmr data. The steric constraint and π p π conjugation are discussed in this work. 相似文献
10.
Braulio Insuasty O Henry Insuasty I Jairo Quiroga P Claudio Saitz Carolina Jullian 《Journal of heterocyclic chemistry》1999,36(3):635-638
New 4-Aryl-6-methyl-8-phenyl-2,3-dihydropyrazolo[3,4-b]diazepines and 4-aryl-8-methyl-6-phenyl-2,3-dihydropyrazolo[4,3-b]diazepines were obtained from the reaction of 4,5-diamino-3-methyl-1-phenylpyrazole 1 with one equivalent of the 3-dimethylaminopropiophenones 2 in absolute ethanol. The structures of 4-aryl-6-methyl-8-phenyl-2,3-dihydropyrazolo[3,4-b]diazepines 3 and 4-aryl-8-methyl-6-phenyl-2,3-dihydropyrazolo[4,3-b]diazepines 4 were determined by detailed nmr measurements. 相似文献
11.
Aldo Andreani Mirella Rambaldi Patricia Carloni Lucedio Greci Pierluigi Stipa 《Journal of heterocyclic chemistry》1989,26(2):525-529
Imidazo[2,1-b]thiazole carbamates and acylureas were prepared by reaction of 5-hydroxymethylimidazo-[2,1-b]thiazole and imidazo[2,1-b]thiazole-5-carboxyamide with arylisocyanates. The products formed depend from the substituent bonded at the 6 position of the imidazothiazole moiety, and from the reaction conditions. 相似文献
12.
A facile approach to the synthesis of 2,3,6-trisubstituted-5,6-dihydroimidazo[2,1-b]thiazole was reported. A resin bound cyclic thiourea was formed by the treatment of a resin bound diamine with 1,1′-thiocarbonyldiimidazole, and then reacted with a α-haloketone to generate a resin bound isothiourea. HF treatment of the resin bound isothiourea resulted in the cleavage of the product and simultaneous formation of an enamine bond. This led to the formation of the 2,3,6-trisubstituted-5,6-dihydroimidazo[2,1-b]thiazole in high yield and purity. 相似文献
13.
A novel reaction for the synthesis of 2,3-dihydroimidazo[2,1-b]oxazoles has been described by condensation of 2,4(5)-dinitroimidazole with a series of oxiranes. 相似文献
14.
Themolysis of naphth[1,2-d]imidazo[2,1-b]thiazole-2,3-dione ( 1 ) in dimethylformamide gave an intermediate 2-isocyanatonaphtho[1,2-d]thiazole ( 2 ), which underwent [4 + 4] cyclodimerization to yield dinaphtho-[1″,2″:4,5;1′″,2′″:4′,5′]dithiazolo[3,2-a:3′,2′-e]-1,3,5,7-tetrazocine-9,19-dione ( 3 ). The possible [4 + 2] cycloadduct, 3-(2-naphtho-[1,2-d]-thiazolyl)naphtho[1′,2′:4,5]thiazolo[3,2-a]-1,3,5-triazine-2,4-dione ( 4 ), an usual dimer type of heterocyclic isocyanates was not produced. Discrimination between the two isomers was established on the basis of spectral analyses. 相似文献
15.
Henri Stalder 《Helvetica chimica acta》1986,69(8):1887-1897
Metabolites of 1,5-Dihydroimidazo[2,1-b ]quinazolin-2(3H)-ones. Preparation and Reactions of Some 1,5-Dihydro-3-hydroxyimidazo[2,1-b]quinazolin-2(3H)-ones Hydroxylated 1,5-dihydroimidazo[2,1-b]quinazolin-2(3H)-ones 2–4 and 6 were isolated as metabolites of imidazoquinazolinones 1a and 1b , respectively. The synthesis of 1,5-dihydro-3-hydroxy-3-methylimidazo[2,1-b]quinazolin-2(3H)-ones 3 , 4 , and 6 , and the preparation of some derivatives thereof is described. 相似文献
16.
N-Phenyl-4-(6-phenylimidazo[2,1-b]thiazol-5-yl)thiazol-2-amines (6a-q) have been synthesized by the Hantzsch thiazole reaction of 2-chloro-1-(6-phenylimidazo[2,1-b]thiazol-5-yl)ethanones (4a-e) with suitably substituted thioureas using microwave heating. The ethanones (4a-e) were prepared by the reaction of 6-phenylimidazo[2,1-b]thiazoles (3a-e) with chloroacetylchloride in refluxing 1,4-dioxane whereas the thiazoles (3a-e) were synthesized by the reaction of 2-bromo-1-phenylethanones (2a-e) with thiazol-2-amine in refluxing acetone. 相似文献
17.
A series of N-(3-dimethylaminopropyl)-6-substituted naphtho[2,1-b]thiophenes-4-carboxamides have been synthesized. 6-Substituted naphtho[2,1-b]thiophene-4-carboxylic acids were obtained upon oxidative-photo-cyclization of α-(2-thienyl)-β-arylacrylic acids. The naphtho[2,1-b]thiophene carboxylic acids were converted to the corresponding amides through their acid chlorides or, in one case, by use of 1,1-carbonyldiimidazole coupling of the amine and the acid. 相似文献
18.
T. L. Hough 《Journal of heterocyclic chemistry》1983,20(4):1003-1005
The conversion of the 5-bromoimidazo[2, 1-b]-1, 3, 4-thiadiazole Ib to the 5-cyano derivative Ic is firstly described. The 5-nitroimidazo[2, 1-b]-1, 3, 4-thiadiazole Id is smoothly reduced by aluminium amalgam to the 5-imino-5, 6-dihydroimidazo[2, 1-b]-1, 3, 4-thiadiazole II. However, reaction of Id with sodium dithionite unexpectedly gives 1, 3, 4-thiadiazoles III and V depending upon conditions. 相似文献
19.
Norton P. Peet James Malecha Michael E. Letourneau Shyam Sunder 《Journal of heterocyclic chemistry》1989,26(1):257-264
New methodology is described for the construction of tricyclic heterocycles. Thus, a double displacement reaction of l-(2-fluorobenzoyl)-2-methylthio-2-imidazoline ( 8a ) with 1,1-dialkylhydrazines gave 10-substituted 2,10-dihydroimidazo[2,1-b]quinazolin-5(3H)-ones in good yield. The corresponding 1-(2-nitrobenzoyl)-2-meth-ylthio-2-imidazolines also underwent double displacement reactions with hydrazines. Other tricyclics made using double displacement reactions were pyrimido[2,1-b]quinazolines, imidazo[1,2-a]pyrido[2,3-d]pyrimidines, and imidazo[1,2-a]pyrazolo[3,4-d]pyrimidines. Treatment of 8a with hydrazine hydrate or methylhydrazine gave products resulting from displacement, but did not afford fused benzotriazepinones. 相似文献
20.
W. David Cotterill Muhammad Iqbal Robert Livingstone Maurice V. Walshaw 《Journal of heterocyclic chemistry》1974,11(3):283-286
The reaction between 3,3-bis(methoxyphenyl)-3H-naphtho[2,1-b]pyran and 1,3-bis(methoxyphenyl)-1H-naphtho[2,1-b]pyran under acid conditions gives a 7a,15a-dihydro-7a,15-bis(methoxyphenyl)-16-[2,2-bis(methoxyphenyl)-l-vinyl]dinaphtho-[2,1-b:2,1-g]-4H,5H-pyrano[2,3-b]-pyran. 相似文献