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1.
rac‐5‐Diphenylacetyl‐2,2,4‐trimethyl‐2,3,4,5‐tetrahydro‐1,5‐benzothiazepine, C26H27NOS, (I), and rac‐5‐formyl‐2,2,4‐trimethyl‐2,3,4,5‐tetrahydro‐1,5‐benzothiazepine, C13H17NOS, (II), are both characterized by a planar configuration around the heterocyclic N atom. In contrast with the chair conformation of the parent benzothiazepine, which has no substituents at the heterocyclic N atom, the seven‐membered ring adopts a boat conformation in (I) and a conformation intermediate between boat and twist‐boat in (II). The molecules lack a symmetry plane, indicating distortions from the perfect boat or twist‐boat conformations. The supramolecular architectures are significantly different, depending in (I) on C—H...O interactions and intermolecular S...S contacts, and in (II) on a single aromatic π–π stacking interaction.  相似文献   

2.
Condensation of 1‐arylhydrazono‐1‐benzotriazol‐1‐yl 2‐propanones ( 5a‐c ) with DMF DMA afforded 1‐aryl‐3‐benzotriazol‐1‐yl‐1,4‐dihydropyridazine‐4‐ones ( 8a‐c ). While condensation of 1‐functionally substituted methylbenzotriazoles 3b,c with 2‐arylhydrazono‐3‐oxoarylpropanal 13a,b give 3‐aroyl‐5‐(benzo‐triazolyl‐1‐yl)‐1,6‐dihydro‐1‐phenylpyridazine‐6‐ones and 6‐imines 14a‐d.  相似文献   

3.
4‐Ethoxycarbonyl‐5‐phenyl‐2,3‐dihydrofuran‐2,3‐dione 1 reacts with aldehydes via the acylketene intermediate 2 giving the 1,3‐dioxin‐4‐ones 3a‐e and the 1,4‐bis(5‐ethoxycarbonyl‐4‐oxo‐6‐phenyl‐4H‐1,3‐dioxin‐2‐yl)benzene 4 , and a one step reaction between dibenzoylmethane and oxalylchloride gave 3,5‐dibenzoyl‐2,6‐diphenyl‐4‐pyrone 7 . The reaction of 1 with dibenzoylmethane, a dicarbonyl compound, provided ethyl 3‐benzoyl‐4‐oxo‐2,6‐diphenylpyran‐5‐carboxylate derivative 9 . Compound 9 was converted into the corresponding ethyl 3‐benzoyl‐4‐hydroxy‐2,6‐diphenylpyridine‐5‐carboxylate derivative 10 via its reaction with ammonium hydroxyde solution in 1 ‐butanol.  相似文献   

4.
The one‐step cyclocondensation of substituted isoflavones (=3‐phenyl‐4H‐1‐benzopyran‐4‐ones) with cyanoacetohydrazide in the presence of KOH afforded a mixture of 1‐amino‐5,6‐diaryl‐3‐cyano‐1H‐2‐pyridin‐2‐ones and 6,7‐diaryl‐4‐cyano‐3‐hydroxy‐1H‐[1,2]diazepines.  相似文献   

5.
The title compound ( 1 ) was isolated in 20‐30% recovery following solvolysis of a mixture of 5‐bromo‐3‐n‐butyl‐4‐methyl‐2‐p‐toluenesulfonylpyrrole ( 4b ) and 5‐bromo‐4‐n‐butyl‐3‐methyl‐2‐p‐toluenesulfonyl‐pyrrole ( 4a ) in trifluoroacetic acid and water, a reaction designed to produce 5‐p‐toluenesulfonyl‐3‐pyrrolin‐2‐ones, e.g., 5a and 5b .  相似文献   

6.
Some new compounds (E)‐3‐aryl‐1‐(5‐methyl‐1‐p‐tolyl‐1H‐1,2,3‐triazol‐4‐yl)‐prop‐2‐en‐1‐ones 5a–e were prepared by 1‐(5‐methyl‐1‐p‐tolyl‐1H‐1,2,3‐triazol‐4‐yl)‐ethanone and various aromatic aldehydes. Then one pot reaction was happened by compounds 5a–e with hydrazine hydrate in acetic acid or propionic acid, respectively, to give the title compounds 1acyl‐5‐aryl‐3‐(5‐methyl‐1‐p‐tolyl‐1H‐1,2,3‐triazol‐4‐yl)‐4,5‐dihydro‐1H‐pyrazoles 6a–i . All structures were established by MS, IR, CHN, 1H‐NMR and 13C‐NMR spectral data. J. Heterocyclic Chem., (2012).  相似文献   

7.
On the Hydrolysis of 2,3‐Dihydro‐1,3‐di‐tert‐butyl‐4,5‐dimethylimidazol‐2‐ylidene. The Crystal Structure of 1,3‐Di‐tert‐butyl‐4,5‐dimethylimidazolium Bicarbonate 1,3‐Di‐tert‐butyl‐4,5‐dimethylimidazolium bicarbonate ( 7 ), formed on the exposure of 2,3‐dihydro‐1,3‐di‐tert‐butyl‐4,5‐dimethylimidazol‐2‐ylidene ( 6 ) towards air, is prepared on the reaction of 6 with ammonium bicarbonate; its crystal structure analysis reveals the presence of dimeric bicarbonate anions linked to each other and to the imidazolium ions with hydrogen bonds.  相似文献   

8.
An easy, highly efficient and a new convenient one‐pot, two‐step approach to the synthesis of 3‐(3‐benzyl‐2‐(phenylimino)‐2,3‐dihydrothiazol‐4‐yl)‐6‐methyl‐4‐(2‐oxo‐2‐phenylethoxy)‐3,4‐dihydro‐2H‐pyran‐2‐one is described. These compounds were synthesized from 3‐(3‐benzyl‐2‐(phenylimino)‐2,3‐dihydrothiazol‐4‐yl)‐4‐hydroxy‐6‐methyl‐3,4‐dihydro‐2H‐pyran‐2‐one and α‐bromoketones in good yields. The compounds 4 were synthesized by a multi‐component reaction between 1 , 2 , and 3 and the prominent features of this protocol are mild reaction conditions, operation simplicity, and good to high yields of products.  相似文献   

9.
The complete assignment of the 1H and 13C NMR spectra of various 2‐acetamido‐3‐mercapto‐3‐methyl‐N‐aryl‐butanamides and 2‐acetamide‐3‐methyl‐3‐nitrososulfanyl‐N‐aryl‐butanamides with p‐methoxy, o‐chloro and m‐chloro substituents is reported. Copyright © 2013 John Wiley & Sons, Ltd.  相似文献   

10.
15‐Cyano‐12‐oxopentadecano‐15‐lactone was synthesized in 59% total yield starting from 2‐nitrocyclododecanone by Michael addition to acrylaldehyde, followed by reaction with trimethylsilylcyanide, hydrolysis, ring‐expansion, and Nef reaction. A two‐step, one‐pot synthesis of intermediate 2‐hydroxy‐4‐(1‐nitro‐2‐oxycyclododecyl)butanenitrile from 3‐(1‐nitro‐2‐oxocyclododecyl)propanal was developed and the conditions for the Nef reaction were studied. 15‐Cyano‐12‐oxopentadecano‐15‐lactam was synthesized in 40% total yield starting from 2‐nitrocyclododecanone by Michael addition to acrylaldehyde, followed by Strecker reaction, ring‐expansion, and Nef reaction. The conditions for the Strecker and Nef reactions were studied. The structures of the target compounds, intermediates, and by‐product were characterized by IR, 1H‐ and 13C‐NMR, and elemental analysis or MS.  相似文献   

11.
X‐ray studies reveal that tert‐butyl (6S)‐6‐iso­butyl‐2,4‐dioxo­piperidine‐1‐carboxyl­ate occurs in the 4‐enol form, viz. tert‐butyl (6S)‐4‐hydroxy‐6‐iso­butyl‐2‐oxo‐1,2,5,6‐tetra­hydropyri­dine‐1‐carboxyl­ate, C14H23NO4, when crystals are grown from a mixture of di­chloro­methane and pentane, and has an axial orientation of the iso­butyl side chain at the 6‐position of the piperidine ring. Reduction of the keto functionality leads predominantly to the corresponding β‐hydroxy­lated δ‐lactam, tert‐butyl (4R,6S)‐4‐hydroxy‐6‐iso­butyl‐2‐oxo­piperidine‐1‐car­boxyl­ate, C14H25NO4, with a cis configuration of the 4‐hydroxy and 6‐iso­butyl groups. The two compounds show similar molecular packing driven by strong O—H⋯O=C hydrogen bonds, leading to infinite chains in the crystal structure.  相似文献   

12.
A series of N‐(3‐amino‐3,4‐dihydro‐4‐oxopyrimidin‐2‐yl)‐4‐chloro‐2‐mercapto‐5‐methylbenzenesulfonamide derivatives 10‐17 have been synthesized as potential anti‐HIV agents. The in vitro anti‐HIV‐1 activity of these compounds has been tested at the national Cancer Institute (Bethesda, MD), and the structure‐activity relationships are discussed. The selected N‐[3‐amino‐3,4‐dihydro‐6‐(tert‐butyl)‐4‐oxothieno[2,3‐e]pyrimidin‐2‐yl]‐4‐chloro‐2‐metcapto‐5‐methylbenzenesulfonamide ( 14 ) showed good anti‐HIV‐1 activity with 50% effective concentration (EC50) value of 15 μM and weak cytotoxic effect (IC50 = 106 μM).  相似文献   

13.
Synthetic routes for the preparation of methyl 2‐amino‐4‐methoxythieno[2,3‐d]pyrimidine‐6‐carboxylate (4) ‐ useful intermediate for lipophilic and classical antifolates from 2‐amino‐4,6‐dichloropyrimidine‐5‐car‐baldehyde (1) have been studied. It has been shown that more efficient synthesis of compound 4 includes the preparation of 4‐methoxy derivative 7 and subsequent tandem substitution/annulation reaction with methyl mercaptoethanoate in dimethylformamide in the presence of potassium carbonate and molecular sieves 4 Å. Compound 4 was used for the synthesis of N‐aryl 2‐amino‐4‐oxo‐3,4‐dihydrothieno[2,3‐d]‐pyrimidine‐6‐carboxamides 10a‐c, including an analog of folic acid with amide bridge ‐ N‐(4‐{[(2‐amino‐4‐oxo‐3,4‐dihydrothieno[2,3‐d]pyrirnidin‐6‐yl)carbonyl]amino}‐benzoyl)‐L‐glutamic acid (10c) .  相似文献   

14.
As part of the structure‐activity relationship of the dopamine D2 and serotonin 5‐HT3 receptors antagonist 1, which is a clinical candidate with a broad antiemetic activity, the synthesis and dopamine D2 and serotonin 5‐HT3 receptors binding affinity of (R)‐5‐bromo‐N‐(1‐ethyl‐3‐methylhexahydro‐1,3‐diazin‐5‐yl)‐ and (R)‐5‐bromo‐N‐(1‐ethyl‐5‐methyloctahydro‐1,5‐diazocin‐3‐yl)‐2‐methoxy‐6‐methylaminopyridine‐3‐carboxam‐ides ( 2 and 3 ) are described. Treatment of 1‐ethyl‐2‐(p‐toluenesulfonyl)amino‐3‐methylaminopropane dihy‐drochloride ( 4a ) with paraformaldehyde and successive deprotection gave the 5‐aminohexahydro‐1,3‐diazine 6 in excellent yield. 3‐Amino‐1‐ethyl‐5‐methyloctahydro‐1,5‐diazocine ( 15 ) was prepared from 2‐(benzyloxycarbonyl)amino‐3‐[[N‐(tert‐butoxycarbonyl)‐N‐methyl]amino]‐1‐ethylaminopropane ( 9 ) through the intramolecular amidation of (R)‐3‐[N‐[(2‐benzyloxycarbonylamino‐3‐methylamino)propyl]‐N‐ethyl]aminopropionic acid trifluoroacetate ( 12 ), followed by lithium aluminum hydride reduction of the resulting 6‐oxo‐1‐ethyl‐5‐methyloctahydrodiazocine ( 13 ) in 41% yield. Reaction of the amines 6 and 15 with 5‐bromo‐2‐methoxy‐6‐methylaminopyridine‐3‐carboxylic acid furnished the desired 2 and 3 , which showed much less potent affinity for dopamine D2 receptors than 1 .  相似文献   

15.
Possible approaches to synthesis of 5‐methyl‐4‐oxo‐2‐(coumarin‐3‐yl)‐N‐aryl‐3,4‐dihydrothieno[2,3‐d]pyrimidine‐6‐carboxamides 4 have been discussed. It is shown that the preferable approach is cyclization of 2‐iminocoumarin‐3‐carboxamides 1 , utilizing 5‐amino‐3‐methyl‐N2‐arylthiophene‐2,4‐dicarboxamides 2 as binucleophilic reagents. The proposed procedure allowed us to easily obtain 4 in two stages, using common reagents. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:341–346, 2007; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20303  相似文献   

16.
The crystal structures of 2,2‐dimethyl‐5‐nitroso‐1,3‐dioxan‐5‐yl benzoate, C13H15NO5, (I), 2,2‐dimethyl‐5‐nitroso‐1,3‐dioxan‐5‐yl 4‐chlorobenzoate, C13H14ClNO5, (II), and 5‐nitroso‐1,3‐dioxan‐5‐yl 4‐chlorobenzoate, C11H11NO5, (III), have been determined in order to gain insight into the conformational preference of α‐benzoyloxynitroso. Unfavourable 1,3‐diaxial interactions force (I) and (II) to crystallize in the 2,5 twist‐boat conformation, whereas compound (III), lacking this destabilizing interaction, crystallizes in the chair conformation.  相似文献   

17.
Herein, we present an innovative, novel, and highly convenient protocol for the synthesis of 3‐(pyridin‐2‐yl)‐5‐sec‐aminobiphenyl‐4‐carbonitriles ( 6a , 6b , 6c , 6d , 6e , 6f , 6g ) and 9,10‐dihydro‐3‐(pyridine‐2‐yl)‐1‐sec‐aminophenanthrene‐2‐carbonitriles ( 10a , 10b , 10c , 10d , 10e ), which have been delineated from the reaction of 4‐sec‐amino‐2‐oxo‐6‐aryl‐2H‐pyran‐3‐carbonitrile ( 4a , 4b , 4c , 4d , 4e , 4f , 4g ) and 4‐sec‐amino‐2‐oxo‐5,6‐dihydro‐2H‐benzo[h]chromene‐3‐carbonitriles ( 9a , 9b , 9c , 9d , 9e ) with 2‐acetylpyridine ( 5 ) through the ring transformation reaction by using KOH/DMF system at RT. The salient feature of this procedure is to provide a transition metal‐free route for the synthesis of asymmetrical 1,3‐teraryls like 3‐(pyridin‐2‐yl)‐5‐sec‐aminobiphenyl‐4‐carbonitriles ( 6a , 6b , 6c , 6d , 6e , 6f , 6g ) and 9,10‐dihydro‐3‐(pyridine‐2‐yl)‐1‐sec‐aminophenanthrene‐2‐carbonitriles ( 10a , 10b , 10c , 10d , 10e ). The novelty of the reaction lies in the creation of an aromatic ring from 2H‐pyran‐2‐ones and 2H‐benzo[h]chromene‐3‐carbonitriles via two‐carbon insertion from 2‐acetylpyridine ( 5 ) used as a source of carbanion.  相似文献   

18.
The cyclization of phenacyl anthranilate has been studied with the aim to develop the synthesis of 2‐(2′‐aminophenyl)‐4‐phenyloxazole. However, a different course of the reaction than expected was observed. 2‐Phenyl‐2‐hydroxymethyl‐4‐oxo‐1,2,3,4‐tetrahydroquinazoline ( 3a ) was formed by the reaction of phenacyl anthranilate ( 2 ) with ammonium acetate under various conditions. 3‐Hydroxy‐2‐phenyl‐4(1H)‐quinolinone ( 4 ) arose by heating compound 3a in acetic acid. The same compound was obtained by melting compound 3a , but the yield was lower. Different types of products resulted in the reaction of compound 3a with acetic anhydride. Under mild conditions acetylated products 2‐acetoxymethyl‐2‐phenyl‐4‐oxo‐1,2,3,4‐tetrahydroquinazoline ( 7a ) and 2‐acetoxymethyl‐3‐acetyl‐2‐phenyl‐4‐oxo‐1,2,3,4‐tetrahydroquinazoline ( 8 ) were prepared. If the reaction was carried out under reflux of the reaction mixture, molecular rearrangement took place to give cis and trans 2‐methyl‐4‐oxo‐3‐(1‐phenyl‐2‐acetoxy)vinyl‐3,4‐dihydroquinazolines ( 9a and 9b ). All prepared compounds have been characterised by their 1H, 13C and 15N NMR spectra, IR spectra and MS.  相似文献   

19.
Some new target products 5‐aryl‐4,5‐dihydro‐3‐(5‐methyl‐1‐p‐tolyl‐1H‐1,2,3‐triazol‐4‐yl)‐1‐(4‐phenylthiazol‐2‐yl)pyrazoles 5a , 5b , 5c , 5d , 5e , 5f , 5g , 5h , 5i , 5j have been synthesized by reaction of 2‐bromo‐1‐phenylethanone and compounds 4a , 4b , 4c , 4d , 4e , 4f , 4g , 4h , 4i , 4j which were prepared from the combination of thiosemicarbazide and (E)‐3‐aryl‐1‐(5‐methyl‐1‐p‐tolyl‐1H‐1,2,3‐triazol‐4‐yl)‐prop‐2‐en‐1‐ones 3a , 3b , 3c , 3d , 3e , 3f , 3g , 3h , 3i , 3j . All the structures were established by MS, IR, CHN, and 1H NMR spectra data. Synthesis of structure diversity is applied. J. Heterocyclic Chem., (2011).  相似文献   

20.
The molecules of N‐(3‐tert‐butyl‐1‐phenyl‐1H‐pyrazol‐5‐yl)‐2‐chloro‐N‐(4‐methoxybenzyl)acetamide, C23H26ClN3O2, are linked into a chain of edge‐fused centrosymmetric rings by a combination of one C—H...O hydrogen bond and one C—H...π(arene) hydrogen bond. In N‐(3‐tert‐butyl‐1‐phenyl‐1H‐pyrazol‐5‐yl)‐2‐chloro‐N‐(4‐chlorobenzyl)acetamide, C22H23Cl2N3O, a combination of one C—H...O hydrogen bond and two C—H...π(arene) hydrogen bonds, which utilize different aryl rings as the acceptors, link the molecules into sheets. The molecules of S‐[N‐(3‐tert‐butyl‐1‐phenyl‐1H‐pyrazol‐5‐yl)‐N‐(4‐methylbenzyl)carbamoyl]methyl O‐ethyl carbonodithioate, C26H31N3O2S2, are also linked into sheets, now by a combination of two C—H...O hydrogen bonds, both of which utilize the amide O atom as the acceptor, and two C—H...π(arene) hydrogen bonds, which utilize different aryl groups as the acceptors.  相似文献   

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