Stereoselective synthesis of (+)-α-Conhydrine was accomplished from protected (R)-(+)-glyceraldehyde, a familiar carbohydrate predecessor. Our synthetic strategy featured the following two key reactions. One is Zn-mediated stereoselective aza-Barbier reaction of imine 6 with allyl bromide to afford chiral homoallylic amine 7, and the other is ring-closing metathesis.
{"title":"Stereoselective Synthesis of (+)-α-Conhydrine from R-(+)-Glyceraldehyde","authors":"Nageshwar Rao Penumati, Nagaiah Kommu","doi":"10.1155/2014/982716","DOIUrl":"https://doi.org/10.1155/2014/982716","url":null,"abstract":"Stereoselective synthesis of (+)-α-Conhydrine was accomplished from protected (R)-(+)-glyceraldehyde, a familiar carbohydrate predecessor. Our synthetic strategy featured the following two key reactions. One is Zn-mediated stereoselective aza-Barbier reaction of imine 6 with allyl bromide to afford chiral homoallylic amine 7, and the other is ring-closing metathesis.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":"26 1","pages":"150-156"},"PeriodicalIF":0.0,"publicationDate":"2014-10-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88192052","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
M. Savant, A. M. Pansuriya, Chirag V. Bhuva, N. Kapuriya, Y. Naliapara
A novel two-step synthesis of 4,5,6,7-tetrahydro-2H-indazole-3-carbohydrazide has been developed. The library of N′-arylmethylene-4,5,6,7-tetrahydro-2H-indazole-3-carbohydrazide was generated by coupling of hydrazide to various aromatic and heterocyclic aldehydes in water media at ambient temperature with great flexibility regarding reaction time and yield.
{"title":"Water Mediated Synthesis of N′-Arylmethylene-4,5,6,7-tetrahydro-2H-indazole-3-carbohydrazide Library","authors":"M. Savant, A. M. Pansuriya, Chirag V. Bhuva, N. Kapuriya, Y. Naliapara","doi":"10.1155/2014/567053","DOIUrl":"https://doi.org/10.1155/2014/567053","url":null,"abstract":"A novel two-step synthesis of 4,5,6,7-tetrahydro-2H-indazole-3-carbohydrazide has been developed. The library of N′-arylmethylene-4,5,6,7-tetrahydro-2H-indazole-3-carbohydrazide was generated by coupling of hydrazide to various aromatic and heterocyclic aldehydes in water media at ambient temperature with great flexibility regarding reaction time and yield.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":"21 1","pages":"1-4"},"PeriodicalIF":0.0,"publicationDate":"2014-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77145968","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
S. Santra, Matiur Rahman, A. Roy, A. Majee, A. Hajra
A green and highly efficient method has been developed for the one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component condensation of aldehydes, 1,3-cyclic diketones, and malononitrile under MW irradiation without using any catalyst and solvent. This transformation presumably occurs by a sequential Knoevenagel condensation, Michael addition, and intramolecular cyclization. Operational simplicity, solvent and catalyst-free conditions, the compatibility with various functional groups, nonchromatographic purification technique, and high yields are the notable advantages of this procedure.
{"title":"Microwave-Assisted Three-Component “Catalyst and Solvent-Free” Green Protocol: A Highly Efficient and Clean One-Pot Synthesis of Tetrahydrobenzo[b]pyrans","authors":"S. Santra, Matiur Rahman, A. Roy, A. Majee, A. Hajra","doi":"10.1155/2014/851924","DOIUrl":"https://doi.org/10.1155/2014/851924","url":null,"abstract":"A green and highly efficient method has been developed for the one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component condensation of aldehydes, 1,3-cyclic diketones, and malononitrile under MW irradiation without using any catalyst and solvent. This transformation presumably occurs by a sequential Knoevenagel condensation, Michael addition, and intramolecular cyclization. Operational simplicity, solvent and catalyst-free conditions, the compatibility with various functional groups, nonchromatographic purification technique, and high yields are the notable advantages of this procedure.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":"38 1","pages":"1-8"},"PeriodicalIF":0.0,"publicationDate":"2014-09-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81547661","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
An efficient high yielding chemoselective synthesis of eleven novel 1-chloro-2-arylcyclohexenes employing the Suzuki cross coupling of 1-bromo-2-chlorocyclohexene with eleven different aryl boronic acids and Pd(dppf) catalyst is reported.
{"title":"A Novel Regiospecific Synthesis of 1-Chloro-2-arylcyclohexenes","authors":"Lokesh Krishnappa, H. Suresh","doi":"10.1155/2014/871595","DOIUrl":"https://doi.org/10.1155/2014/871595","url":null,"abstract":"An efficient high yielding chemoselective synthesis of eleven novel 1-chloro-2-arylcyclohexenes employing the Suzuki cross coupling of 1-bromo-2-chlorocyclohexene with eleven different aryl boronic acids and Pd(dppf) catalyst is reported.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":"39 1","pages":"133-138"},"PeriodicalIF":0.0,"publicationDate":"2014-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76542898","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
S. Habibi‐Khorassani, M. Maghsoodlou, M. Shahraki, Sadegh Talaiefar, Jasem Aboonajmi
Sodium acetate was applied as an efficient catalyst for the one-pot, three-component condensation reactions consisting of 4-nitrobenzaldehyde 2, malononitrile 3, and thiobarbituric acid 1. Use of nontoxic reaction components, short reaction times, environmental, easy work-up, and high yields are some remarkable advantages of this method. Kinetics and mechanism of the reaction were spectrally studied and the second order rate constant (kovr = k1) was automatically calculated by the standard equations contained within the program. The second order rate constant [Ln(kovr = k1), Ln(kovr = k1)/T] that depended on reciprocal temperature was in good agreement with the Arrhenius and Eyring equations, respectively. This data provided the suitable plots for calculating the activation energy and parameters (Ea, ΔG‡, ΔS‡, and ΔH‡) of the reaction. Furthermore, from studying the effects of solvent, concentration, and catalyst on the reaction rate, useful information was obtained regarding the mechanism. The results showed that the first step of the reaction mechanism is a rate determining step (RDS). The proposed mechanism was confirmed in accordance with the experimental data and also the steady state approximation.
{"title":"Kinetic and Mechanistic Investigation of Pyrano[2,3-d]pyrimidine Formation in the Presence of Catalyst under Novel One-Pot Three-Component Reaction","authors":"S. Habibi‐Khorassani, M. Maghsoodlou, M. Shahraki, Sadegh Talaiefar, Jasem Aboonajmi","doi":"10.1155/2014/210327","DOIUrl":"https://doi.org/10.1155/2014/210327","url":null,"abstract":"Sodium acetate was applied as an efficient catalyst for the one-pot, three-component condensation reactions consisting of 4-nitrobenzaldehyde 2, malononitrile 3, and thiobarbituric acid 1. Use of nontoxic reaction components, short reaction times, environmental, easy work-up, and high yields are some remarkable advantages of this method. Kinetics and mechanism of the reaction were spectrally studied and the second order rate constant (kovr = k1) was automatically calculated by the standard equations contained within the program. The second order rate constant [Ln(kovr = k1), Ln(kovr = k1)/T] that depended on reciprocal temperature was in good agreement with the Arrhenius and Eyring equations, respectively. This data provided the suitable plots for calculating the activation energy and parameters (Ea, ΔG‡, ΔS‡, and ΔH‡) of the reaction. Furthermore, from studying the effects of solvent, concentration, and catalyst on the reaction rate, useful information was obtained regarding the mechanism. The results showed that the first step of the reaction mechanism is a rate determining step (RDS). The proposed mechanism was confirmed in accordance with the experimental data and also the steady state approximation.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":"97 1","pages":"1-10"},"PeriodicalIF":0.0,"publicationDate":"2014-05-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"72915934","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
This paper describes an alternative and simple procedure for the synthesis of Ibuprofen using Silica-Supported Preyssler Nanoparticles (H14[NaP5W30O110]/SiO2) (SPNPs), as an eco-friendly, inexpensive, and efficient catalyst. High yields, simplicity of operation, and easy work-up procedure are some advantages of this protocol. Silica-Supported Preyssler Nanoparticles (H14[NaP5W30O110]/SiO2) (SPNPs) offer the advantages of a higher hydrolytic and thermal stability. The salient features of Preyssler’s anion are availability, nontoxicity and reusability. We believe this methodology can find usefulness in organic synthesis.
{"title":"Synthesis of Ibuprofen Using Silica-Supported Preyssler Nanoparticles as an Eco-Friendly, Inexpensive, and Efficient Catalyst","authors":"A. Gharib, N. Pesyan, L. V. Fard, M. Roshani","doi":"10.1155/2014/906801","DOIUrl":"https://doi.org/10.1155/2014/906801","url":null,"abstract":"This paper describes an alternative and simple procedure for the synthesis of Ibuprofen using Silica-Supported Preyssler Nanoparticles (H14[NaP5W30O110]/SiO2) (SPNPs), as an eco-friendly, inexpensive, and efficient catalyst. High yields, simplicity of operation, and easy work-up procedure are some advantages of this protocol. Silica-Supported Preyssler Nanoparticles (H14[NaP5W30O110]/SiO2) (SPNPs) offer the advantages of a higher hydrolytic and thermal stability. The salient features of Preyssler’s anion are availability, nontoxicity and reusability. We believe this methodology can find usefulness in organic synthesis.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":"27 1","pages":"1-6"},"PeriodicalIF":0.0,"publicationDate":"2014-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85564552","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
P. Kumar, Y. D. Reddy, C. V. Reddy, B. Devi, P. Dubey
Phthalic anhydride was treated with secondary amines in acetic acid yielding 2-(diethyl (or) 4-alkylpiperazine or morpholine-1-carbonyl) benzoic acids. The latter were reacted, again, with secondary amines and arylamines by using the coupling reagent HATU and Et3N as a base in DMF giving the novel symmetrical o-phthalic acid diamides , unsymmetrical o-phthalic acid diamides , and primary amidic-secondary amidic containing unsymmetrical o-phthalic acid diamides , respectively.
{"title":"Synthesis of Novel Symmetrical and Unsymmetrical o-Phthalic Acid Diamides","authors":"P. Kumar, Y. D. Reddy, C. V. Reddy, B. Devi, P. Dubey","doi":"10.1155/2014/576715","DOIUrl":"https://doi.org/10.1155/2014/576715","url":null,"abstract":"Phthalic anhydride was treated with secondary amines in acetic acid yielding 2-(diethyl (or) 4-alkylpiperazine or morpholine-1-carbonyl) benzoic acids. The latter were reacted, again, with secondary amines and arylamines by using the coupling reagent HATU and Et3N as a base in DMF giving the novel symmetrical o-phthalic acid diamides , unsymmetrical o-phthalic acid diamides , and primary amidic-secondary amidic containing unsymmetrical o-phthalic acid diamides , respectively.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":"42 1","pages":"1-9"},"PeriodicalIF":0.0,"publicationDate":"2014-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73505850","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A very simple, mild, efficient, and novel green methodology has been developed for the syntheses of some 2-hetero/styryl-benzimidazoles. Title compounds were synthesized by the condensation of -phenylenediamine with cinnamic acids at 150–180°C for 5-6 h using glycerol containing triacetylborate (10–20 mol%) as the reaction medium. In an alternative approach, condensation of 2-methylbenzimidazole derivatives with aromatic aldehydes was done using glycerol containing triacetylborate (10–20 mol%) as the reaction medium.
{"title":"Glycerol Containing Triacetylborate Mediated Syntheses of Novel 2-Heterostyryl Benzimidazole Derivatives: A Green Approach","authors":"Ashok Kumar Taduri, P. K. Babu, B. Devi","doi":"10.1155/2014/260726","DOIUrl":"https://doi.org/10.1155/2014/260726","url":null,"abstract":"A very simple, mild, efficient, and novel green methodology has been developed for the syntheses of some 2-hetero/styryl-benzimidazoles. Title compounds were synthesized by the condensation of -phenylenediamine with cinnamic acids at 150–180°C for 5-6 h using glycerol containing triacetylborate (10–20 mol%) as the reaction medium. In an alternative approach, condensation of 2-methylbenzimidazole derivatives with aromatic aldehydes was done using glycerol containing triacetylborate (10–20 mol%) as the reaction medium.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":"57 4 1","pages":"1-9"},"PeriodicalIF":0.0,"publicationDate":"2014-04-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90113276","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Ozoh Chinwe Francisca, O. U. Chris, Ugwu D. Izuchukwu
A new class of N-(heteroaryl-substituted)-p-toluenesulphonamides has been synthesized exhibiting antibacterial and antifungal properties. The condensation reaction of p-toluenesulphonyl chloride 1 with appropriate substituted amino pyridines 2a–g in acetone furnished N-(heteroaryl-substituted)-p-toluenesulphonamides 3a–g. These derivatives were characterized by IR, 1H-, and 13C-NMR spectroscopy and were screened in vitro against gram-positive bacteria, gram-negative bacteria, and fungi organisms using agar-diffusion method. Results indicated improved biological activities over reference drugs such as Tetracycline (TCN) and Fluconazole (FLU).
{"title":"Synthesis and Antimicrobial Activities of N-(Heteroaryl-substituted)-p-toluenesulphonamides","authors":"Ozoh Chinwe Francisca, O. U. Chris, Ugwu D. Izuchukwu","doi":"10.1155/2014/748257","DOIUrl":"https://doi.org/10.1155/2014/748257","url":null,"abstract":"A new class of N-(heteroaryl-substituted)-p-toluenesulphonamides has been synthesized exhibiting antibacterial and antifungal properties. The condensation reaction of p-toluenesulphonyl chloride 1 with appropriate substituted amino pyridines 2a–g in acetone furnished N-(heteroaryl-substituted)-p-toluenesulphonamides 3a–g. These derivatives were characterized by IR, 1H-, and 13C-NMR spectroscopy and were screened in vitro against gram-positive bacteria, gram-negative bacteria, and fungi organisms using agar-diffusion method. Results indicated improved biological activities over reference drugs such as Tetracycline (TCN) and Fluconazole (FLU).","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":" 11","pages":"1-5"},"PeriodicalIF":0.0,"publicationDate":"2014-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91415187","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
An efficient method for the synthesis of N-tert-butyl amides by reaction of nitriles with tert-butyl acetate or tert-butanol is described using oxalic acid dihydrate in solvent-free condition. The result showed that tert-butyl acetate served as a relatively better source of tert-butyl carbocation than tert-butanol.
{"title":"An Efficient Method for Synthesis of N-tert-Butyl Amides Using Oxalic Acid Dihydrate in Solvent-Free Condition","authors":"M. Mokhtary, Seyedeh Khadijeh Nasernezhad","doi":"10.1155/2014/617153","DOIUrl":"https://doi.org/10.1155/2014/617153","url":null,"abstract":"An efficient method for the synthesis of N-tert-butyl amides by reaction of nitriles with tert-butyl acetate or tert-butanol is described using oxalic acid dihydrate in solvent-free condition. The result showed that tert-butyl acetate served as a relatively better source of tert-butyl carbocation than tert-butanol.","PeriodicalId":19688,"journal":{"name":"Organic Chemistry International","volume":"12 1","pages":"85-88"},"PeriodicalIF":0.0,"publicationDate":"2014-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73269225","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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