- Preparation of spiro[imidazolidine-4,3′-indolin]-2′-imines: Via copper(i)-catalyzed formal [2 + 2 + 1] cycloaddition of 3-diazoindolin-2-imines and triazines
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We report a facile and efficient synthesis of spiro[imidazolidine-4,3′-indolin]-2′-imines via a copper(i)-catalyzed cascade reaction of 3-diazoindolin-2-imines with 1,3,5-triazines. The reaction proceeds under very mild conditions and tolerates a variety of functional groups. The cascade process involves the formation of a copper-carbene intermediate and a formal [2 + 2 + 1] cycloaddition.
- Zhou, Yuxuan,Ma, Fanghui,Lu, Ping,Wang, Yanguang
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- Gold-Catalyzed Formal [4+1]/[4+3] Cycloadditions of Diazo Esters with Triazines
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Reported herein is the unprecedented gold-catalyzed formal [4+1]/[4+3] cycloadditions of diazo esters with hexahydro-1,3,4-triazines, thus providing five- and seven-membered heterocycles in moderate to high yields under mild reaction conditions. These reactions feature the use of a gold complex to accomplish the diverse annulations and the first example of the involvement of a gold metallo-enolcarbene in a cycloaddition. It is also the first utilization of stable triazines as formal dipolar adducts in the carbene-involved cycloadditions. Mechanistic investigations reveal that the triazines reacted directly, rather than as formaldimine precursors, in the reaction process.
- Zhu, Chenghao,Xu, Guangyang,Sun, Jiangtao
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- Activation Relay on Rhodium-Catalyzed C-H Aminomethylation in Cooperation with Photoredox Catalysis
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A site selective C-H aminomethylation at indole's C3 position has been achieved by merging rhodium(III)-catalyzed C-H activation and photoredox catalysis in a one-pot manner. An investigation of the mechanistic insights rationalized the essence of the activation relay and the combination mode.
- Liu, Ruixing,Liu, Jiaxin,Wei, Yin,Shi, Min
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- Synthesis of julolidines via one-pot cascade three component Povarov reaction in the presence of silica sulfuric acid
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In this report, synthesis of julolidines via one-pot cascade reaction of aniline derivatives with a mixture of styrene and formaldehyde in the presence of silica sulfuric acid as an efficient catalyst has been studied under aerobic condition. By presented
- Kaboudin, Babak,Sohrabi, Masoumeh,Kazemi, Foad
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- Gold-Catalyzed Tandem Dual Heterocyclization of Enynones with 1,3,5-Triazines: Bicyclic Furan Synthesis and Mechanistic Insights
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A general and unprecedented gold-catalyzed tandem dual heterocyclization reaction of enynones with 1,3,5-triazines has been developed, which provides bicyclic fused furans in high to excellent yields under mild reaction conditions. In addition, mechanistic studies indicate that the reaction goes through a stepwise [3+2+2]-cycloaddition of furanyl gold intermediate, which is generated from gold-catalyzed cyclization of enynone, with two molecules of formaldimines derived in situ from 1,3,5-triazine, instead of formal [4+3]-cycloaddition.
- Zheng, Yang,Chi, Yongjian,Bao, Ming,Qiu, Lihua,Xu, Xinfang
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- A facile and efficient ultrasound-assisted synthesis of 1,3,5-tris-arylhexahydro-1,3,5-triazine through mannich reaction
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In this paper, we report a facile and efficient method for the synthesis of 1,3,5-tris-arylhexahydro-1,3,5-triazines by reaction of formaldehyde and aromatic amines catalyzed by triethylamine (Et3N) and assisted by ultrasound at rt. This method has the advantages of short reaction times, good.
- Zhong, Xiaoxing,Dou, Guolan
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- Synthesis of Diversely Substituted Imidazolidines via [3+2] Cycloaddition of 1,3,5-Triazinanes with Donor-Acceptor Aziridines and Their Anti-Tumor Activity
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A Y(OTf)3-catalyzed [3+2] cycloaddition of 1,3,5-triazinanes with donor-acceptor aziridines has been developed, accessing diversely substituted imidazolidines high efficiency. Mechanistic investigations support the formation of imidazolidines through an SN1-like pathway. Furthermore, these imidazolidines exhibit promising anti-tumor activity against a series of human cancer cell lines. (Figure presented.).
- Shi, Zhichao,Fan, Tingting,Zhang, Xun,Zhan, Feng,Wang, Zhe,Zhao, Lei,Lin, Jin-Shun,Jiang, Yuyang
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supporting information
p. 2619 - 2624
(2021/04/05)
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- Divergent Synthesis of Aziridine and Imidazolidine Frameworks under Blue LED Irradiation
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We develop a visible light-promoted divergent cycloaddition of α-diazo esters with hexahydro-1,3,5-triazines, leading to a series of aziridine and imidazolidine frameworks in average good yield, by simply changing the reaction media used. It is noteworthy that the reaction occurs under sole visible light irradiation without the need for exogenous photoredox catalysts. More significantly, a reasonable reaction mechanism was proposed on the basis of the control experiments and density functional theory calculation results.
- Cheng, Xiao,Cai, Bao-Gui,Mao, Hui,Lu, Juan,Li, Lei,Wang, Kun,Xuan, Jun
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supporting information
p. 4109 - 4114
(2021/05/26)
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- Synthesis of α-Amino Tertiary Alkylperoxides by Lewis Acid-Catalyzed Peroxidation of 1,3,5-Triazines
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α-Substituted peroxides have been found in natural products and are widely used as anti-malarial agents. Zn(OTf)2-catalyzed peroxidation of 1,3,5-triazines has been developed, accessing diversely substituted α-amino tertiary alkylperoxides with high efficiency. Mechanistic investigations and useful synthetic application of the products have also been presented.
- Liu, Lijuan,Shi, Zhichao,Zhang, Xun,Zhan, Feng,Lin, Jin-Shun,Jiang, Yuyang
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supporting information
p. 3487 - 3491
(2021/09/20)
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- Vinylethylene Carbonates as α,β-Unsaturated Aldehyde Surrogates for Regioselective [3 + 3] Cycloaddition
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Herein, we report a novel stepwise addition-controlled ring size method, to access tetrahydropyrimidines through an operationally simple [3 + 3] cycloaddition of vinylethylene carbonates with triazinanes. Interestingly, we could also use this method for a [3 + 3] oxidative cycloaddition, which allows the facile synthesis of polysubstituted terphenyls under mild conditions. Mechanistic studies suggest that vinylethylene carbonates could generate α,β-unsaturated aldehydes as 3-carbon synthons for cycloaddition via a combination process of Pd-catalyzed decarboxylation and β-H elimination.
- Xu, Yi,Chen, Lu,Yang, Yu-Wen,Zhang, Zhiqiang,Yang, Weibo
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supporting information
p. 6674 - 6678
(2019/09/03)
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- Divergent synthesis of N-heterocycles by Pd-catalyzed controllable cyclization of vinylethylene carbonates
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Here, we report a palladium-catalyzed controllable cyclization of vinyl ethylene carbonates that proceeds through formal migration [2+3] and [5+2] cycloadditions, respectively, under mild conditions. The transformation described here affords a series of synthetically versatile 5,7-membered N-heterocycles which are found in natural products and pharmaceuticals with biological and medicinal properties.
- Yang, Yuwen,Yang, Weibo
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supporting information
p. 12182 - 12185
(2018/11/21)
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- Hydroheteroarylation of Unactivated Alkenes Using N-Methoxyheteroarenium Salts
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We report the first reductive coupling of unactivated alkenes with N-methoxy pyridazinium, imidazolium, quinolinium, and isoquinolinium salts under hydrogen atom transfer (HAT) conditions, and an expanded scope for the coupling of alkenes with N-methoxy pyridinium salts. N-Methoxy pyridazinium, imidazolium, quinolinium, and isoquinolinium salts are accessible in 1-2 steps from the commercial arenes or arene N-oxides (25-99%). N-Methoxy imidazolium salts are accessible in three steps from commercial amines (50-85%). In total 36 discrete methoxyheteroarenium salts bearing electron-donating, electron-withdrawing, alkyl, aryl, halogen, and haloalkyl substituents were prepared (several in multigram quantities) and coupled with 38 different alkenes. The transformations proceed under neutral conditions at ambient temperature, provide monoalkylation products exclusively, and form a single alkene addition regioisomer. Preparatively useful and complementary site selectivities in the addition of secondary and tertiary radicals to pyidinium salts are documented: harder secondary radicals favor C-2 addition (2->10:1), while softer tertiary radicals favor bond formation to C-4 (4.7->29:1). A diene possessing a 1,2-disubstituted and 2,2-disubstituted alkene undergoes hydropyridylation at the latter exclusively (61%) suggesting useful site selectivities can be obtained in polyene substrates. The methoxypyridinium salts can also be employed in dehydrogenative arylation, borono-Minisci, and tandem arylation processes. Mechanistic studies support the involvement of a radical process.
- Ma, Xiaoshen,Dang, Hester,Rose, John A.,Rablen, Paul,Herzon, Seth B.
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supporting information
p. 5998 - 6007
(2017/05/04)
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- Synthesis of hexahydro-symtriazines using PEG-400 as superior solvent
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1,3,5-Hexahydrotriazine derivatives show broad spectrum of biological activities such as anticancer, antitumor. Some of their derivatives are used as carcenolytics, herbicides and show antidote and growth stimulating activities. Very few methodologies are reported for the synthesis of symtriazines. Synthesis of trimer of hexahydrotriazines is pH sensitive reaction and instead of using any acidic and basic conditions, we tried to synthesize this trimer under neutral conditions. Methods: Synthesis of 1,3,5-hexahydro symtriazine derivatives has been achieved by treating parasubstituted aniline with solution of paraformaldehyde using PEG-400 as neutral medium using grindstone method. Results: Symtriazine derivatives were synthesized in good to excellent yields (95-70%) within a short time of 5-7 minutes by grindstone technique using PEG-400 as neutral solvent medium. All the synthesized compounds were characterized by 1HNMR, 13CNMR, Mass and Melting point. Conclusion: This is the first report for the synthesis of 1,3,5-hexahydro-sym-triazine trimer starting from aniline/substituted aniline and paraformaldehyde in the presence of reusable and environmental friendly solvent media PEG-400 by grindstone technique.
- Bondle, Giribala M.,Jadhav, Rohit G.,Kamble, Vinod T.,Atkore, Sandeep T.
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- Synthesis of sulfanylidene-diazaspirocycloalkanones in a three-component Mannich-type reaction catalyzed with lactic acid
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The aminomethylation of thioamides containing an acidic hydrogen atom at the a-carbon atom was investigated as a general reaction. Spirohexahydropyrimidines were obtained in the one-pot, three-component reaction of a variety of cyclic-ketone-derived thioamides, primary amines and formaldehyde with lactic acid acting as a catalyst. The results of our experiments confirmed the high catalytic efficiency of lactic acid. A proper choice of the starting thioamides and amines makes it possible to use this reaction methodolgy to synthesize several new and potentially useful derivatives of hexahydropyrimidine, e.g., biologically-active compounds.
- Jagodziński, Tadeusz S.,So?nicki, Jacek G.,Struk, ?ukasz
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- Enantioselective Mannich Reaction Employing 1,3,5-Triaryl-1,3,5-triazinanes Catalyzed by Chiral-at-Metal Rhodium Complexes
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Chiral-at-metal RhIII complexes catalyze the efficient enantioselective Mannich reaction of 2-acyl imidazoles with 1,3,5-triazinanes, affording the corresponding adducts in 81–99 % yield with up to >99 % enantioselectivity. This protocol performs with 0.1 mol-% of RhIII complex on gram scale without any loss in enantioselectivity.
- Gong, Jun,Li, Shi-Wu,Qurban, Saira,Kang, Qiang
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supporting information
p. 3584 - 3593
(2017/07/22)
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- Task-specific ionic liquid-mediated facile synthesis of 1,3,5 triaryltriazines by cyclotrimerization of imines and their biological evaluation
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A highly efficient method for the synthesis of fluorinated 1,3,5-triaryltriazine derivatives is developed by the condensation reaction of aromatic amines and formaldehyde followed by spontaneous cyclotrimerization using task-specific 1,1,3,3-tetramethylguanidine trifluoroacetate [TMG][Tfa] ionic liquid as a environmentally benign solvent in excellent yields at room temperature. The synthesized compounds were subjected for in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv strain using the LoewensteinJensen medium.
- Dandia, Anshu,Jain, Anuj K.,Sharma, Sonam
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supporting information
p. 521 - 523
(2014/04/17)
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- AZOLE DERIVATIVE
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The present invention provides agents for treating or preventing diseases such as mood disorder, anxiety disorder, schizophrenia, Alzheimer's disease, Parkinson's disease, Huntington's chorea, eating disorder, hypertension, gastrointestinal disease, drug addiction, epilepsy, cerebral infarction, cerebral ischemia, cerebral edema, head injury, inflammation, immune-related disease, alopecia, and so forth. Specifically, the invention provides azole derivatives represented by general formula (I), or pharmaceutically acceptable salts thereof that have an antagonistic action against the arginine-vasopressin (AVP) V1b receptor:
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Paragraph 0501; 0502
(2014/09/17)
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- Facile and efficient synthesis of C3-symmetric benzoxazine: A novel tri-arm molecular scaffold
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Six novel C3-symmetric benzoxazines (1a-f) were synthesized via a one-pot condensation, in which twelve covalent bonds were formed up to 96% yield. Two X-ray crystal structures confirmed their proposed conformations and showed their potential a
- Singh, Rajiv,Schober, Matthew,Hou, Xiaodong,Seay, Alys,Chu, Qianli
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supporting information; experimental part
p. 173 - 175
(2012/01/17)
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- Synthesis of N-substituted 1,3,5-triazacyclohexanes catalyzed by starch sulfuric acid
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N-substituted 1,3,5-triazacyclohexanes were simply synthesized from the reaction of aromatic or fatty amines and formaldehyde catalyzed by recyclable starch sulfuric acid with good yields at room temperature.
- Wu, Hui,Yuan, Rui,Wan, Yu,Yin, Wei,Pang, Li-Ling
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experimental part
p. 1097 - 1102
(2012/03/11)
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- An efficient approach to 1,3,5-tris-arylhexahydro-1,3,5-triazines
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In this paper we report a facile and efficient procedure for the synthesis of 1,3,5-tris-arylhexahydro-1,3,5-triazines (3) by reaction of anilines 1 with 1,3,6,8-tetrazatricyclo[4.4.1.13,8]-dodecane (TATD) (2). The diequatorial chair conformational preference of 3b (Ar=p-tolyl) in the solid state was established by X-ray crystallography and agrees well with molecular mechanics calculations.
- Rivera, Augusto,Torres, Olga Lucia,Leiton, Jesus D.,Morales-Rios, Martha S.,Joseph-Nathan, Pedro
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p. 1407 - 1414
(2007/10/03)
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- Revisitation of Formaldehyde Aniline Condensation. VII. 1,3,5-Triarylhexahydro-sym-triazines and 1,3,5,7-Tetraaryl-1,3,5,7-tetrazocines from Aromatic Amines and Paraformaldehyde
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A product study of the reaction between a number of aromatic amines substituted with widely different groups and paraformaldehyde in inert solvents was performed and found to yield 1,3,5-triaryl-1,3,5-hexahydrotriazines, 1,3,5,7-tetraaryl-1,3,5,7-tetrazocines and formaminals.It was not possible to correlate the product outcomes with the actual structure of the amine substrate.The X-ray diffraction structural determination of 1,3,5-tri-(t-butylphenyl)- (1b) and 1,3,5-tri-(m-fluorophenyl)-1,3,5-hexahydrotriazine (1c) showed the diaxial arrangement of the N-substituents.
- Giumanini, Angelo G.,Verardo, Giancarlo,Zangrando, Ennio,Lassiani, Lucia
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p. 1087 - 1103
(2007/10/02)
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