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1.
Unprecedented Oxycyanation of Methylenecyclopropanes for the Facile Synthesis of Benzoxazine Compounds Containing a Cyano Group
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Yu‐Chao Yuan Dr. Hai‐Bin Yang Prof. Dr. Xiang‐Ying Tang Prof. Dr. Yin Wei Prof. Dr. Min Shi 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(15):5146-5150
A novel intramolecular oxycyanation of methylenecyclopropanes is reported that proceeds through oxidative cleavage of the N?CN bond and subsequent palladium transfer from N to O of the amide group. A range of substituted benzo[d][1,3]oxazines with a cyano group are readily furnished by this newly developed oxycyanation reaction. Tris(4‐trifluoromethylphenyl)phosphine as a ligand has been found to be crucial to effectively promote the transformation with high chemo‐ and regioselectivity. Moreover, the reaction outcome can be significantly affected by the electronic effect of the acyl group attached to the nitrogen atom of methylenecyclopropanes. When R3 is a chloromethyl group, the pyrrolo[2,3‐b]quinoline derivative is obtained by thermal‐induced [3+2] cycloaddition of methylenecyclopropane to the methanediimine intermediate. 相似文献
2.
Rhodium(III)‐Catalyzed [3+2] Annulation of 5‐Aryl‐2,3‐dihydro‐1H‐pyrroles with Internal Alkynes through C(sp2)H/Alkene Functionalization
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Ming‐Bo Zhou Rui Pi Ming Hu Yuan Yang Ren‐Jie Song Dr. Yuanzhi Xia Prof. Dr. Jin‐Heng Li 《Angewandte Chemie (International ed. in English)》2014,53(42):11338-11341
This study describes a new rhodium(III)‐catalyzed [3+2] annulation of 5‐aryl‐2,3‐dihydro‐1H‐pyrroles with internal alkynes using a Cu(OAc)2 oxidant for building a spirocyclic ring system, which includes the functionalization of an aryl C(sp2)? H bond and addition/protonolysis of an alkene C?C bond. This method is applicable to a wide range of 5‐aryl‐2,3‐dihydro‐1H‐pyrroles and internal alkynes, and results in the assembly of the spiro[indene‐1,2′‐pyrrolidine] architectures in good yields with excellent regioselectivities. 相似文献
3.
Khosrow Jadidi 《Tetrahedron》2009,65(10):2005-43
A simple and efficient cyclocondensation reaction of 2,6-diaminopyrimidin-4(3H)-one and isatins for the synthesis of spiro[pyrimido[4,5-b]quinoline-5,5′-pyrrolo[2,3-d]pyrimidine] and spiro[indoline-pyrido[2,3-d:6,5-d′]dipyrimidine] derivatives is reported. 相似文献
4.
Ming‐Bo Zhou Rui Pi Ming Hu Yuan Yang Ren‐Jie Song Yuanzhi Xia Jin‐Heng Li 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2014,126(42):11520-11523
This study describes a new rhodium(III)‐catalyzed [3+2] annulation of 5‐aryl‐2,3‐dihydro‐1H‐pyrroles with internal alkynes using a Cu(OAc)2 oxidant for building a spirocyclic ring system, which includes the functionalization of an aryl C(sp2) H bond and addition/protonolysis of an alkene CC bond. This method is applicable to a wide range of 5‐aryl‐2,3‐dihydro‐1H‐pyrroles and internal alkynes, and results in the assembly of the spiro[indene‐1,2′‐pyrrolidine] architectures in good yields with excellent regioselectivities. 相似文献
5.
《中国化学》2017,35(9):1422-1430
The base promoted three‐component reaction of β‐ enamino imide, malononitrile and various cyclic α‐ diketones in acetonitrile showed interesting molecular diversity. The reactions with acenaphthylene‐1,2‐dione and ninhydrin afforded functionalized spiro[indene‐2,4'‐pyrrolo[3,4‐b ]pyridines] and spiro[acenaphthylene‐1,4'‐pyrrolo[3,4‐b ]pyridines] in good yields. The similar reaction of phenanthrene‐9,10‐dione resulted in the formation of the unexpected complex phenanthro[9',10':4,5]furo[2,3‐c ]pyrrolo[3,4‐b ]pyrroles in satisfactory yields. 相似文献
6.
《中国化学会会志》2017,64(6):690-698
An efficient and green strategy for the improved synthesis of a biologically and pharmaceutically interesting multi‐functionalized diverse novel spiro‐benzo[a ]phenazine annulated heterocycles was developed with the assistance of microwave irradiation. A sequential one‐pot, two‐step domino reaction starting from 2‐hydroxynaphthalene‐1,4‐dione, benzene‐1,2‐diamines, a cyclic carbonyl compound, and 1,3‐indandione in the presence of a basic ionic liquid (1‐butyl‐3‐methylimidazolium hydroxide) as an expedient, ecofriendly and reusable catalyst afforded the corresponding novel spiro[benzo[a ]indeno[2′,1′:5,6]pyrano[2,3‐c ]phenazine] derivatives with high yield under solvent‐free conditions. This domino Knoevenagel–Michael annulation reaction provided five new bonds (two C–C, two CN, and one C–O) and two new rings through multiple operations in a single flask. 相似文献
7.
Afsaneh Feiz Ghazaleh Imani Shakibaei Zahra Yasaei Hamid Reza Khavasi Ayoob Bazgir 《Helvetica chimica acta》2011,94(9):1628-1637
A new four‐component synthesis of spiro[4H‐indeno[1,2‐b]pyridine‐4,3′‐[3H]indoles] and spiro[acenaphthylene‐1(2H),4′‐[4H‐indeno[1,2‐b]pyridines] by the reaction of indane‐1,3‐dione, 1,3‐dicarbonyl compounds, isatins (=1H‐indole‐2,3‐diones) or acenaphthylene‐1,2‐dione, and AcONH4 in refluxing toluene in the presence of a catalytic amount of pyridine is reported. 相似文献
8.
《Journal of heterocyclic chemistry》2017,54(1):465-472
An efficient approach for the synthesis of pharmacologically important spiro[indoline‐3,4'‐pyrano[2,3‐c]pyrazole] derivatives from tandem, four component reaction of various hydrazines, isatins, β‐ketoesters, and malononitrile or methyl(ethyl)cyanoester in the presence of N,N,N',N'‐tetrabromobenzene‐1,3‐disulfonamide [ TBBDA ] and poly(N,N'‐dibromo‐N‐ethyl‐benzene‐1,3‐disulfonamide) [ PBBS ] as efficient organocatalysts was reported. 相似文献
9.
N-Heterocyclic carbene derived 2-phenylthiocarbamoyl benzimidazolium and imidazolinium inner salts are a unique ambident C-C-S and C-C-N 1,3-dipolar system able to undergo highly efficient and regioselective cycloaddition with dimethyl acetylenedicarboxylate and ethyl propiolate to furnish, respectively, spiro[imidazole-2,3'-thiophene] and spiro[imidazole-2,3'-pyrrole] derivatives in good to excellent yields. 相似文献
10.
Axelle Arrault Jean‐Yves Mrour Jean‐Michel Lger Christian Jarry Grald Guillaumet 《Helvetica chimica acta》2001,84(8):2198-2211
A one‐step synthesis of ethyl 2,3‐dihydronaphtho[1,2‐b]furan‐2‐carboxylate and/or ethyl 4′‐oxospiro[cyclopropane‐1,1′(4′H)‐naphthalene]‐2′‐carboxylate derivatives 2 and 3 , respectively, from substituted naphthalen‐1‐ols and ethyl 2,3‐dibromopropanoate is described (Scheme 1). Compounds 2 were easily aromatized (Scheme 2). In the same way, 3,4‐dibromobutan‐2‐one afforded the corresponding 1‐(2,3‐dihydronaphtho[1,2‐b]furan‐2‐yl)ethanone and/or spiro derivatives 8 and 9 , respectively (Scheme 6). A mechanism for the formation of the dihydronaphtho[1,2‐b]furan ring and of the spiro compounds 3 is proposed (Schemes 3 and 4). The structures of spiro compounds 3a and 3f were established by X‐ray structural analysis. The reactivity of compound 3a was also briefly examined (Scheme 9). 相似文献
11.
《Journal of heterocyclic chemistry》2018,55(7):1554-1563
The reaction of compound 2‐amino‐3‐cyano‐6‐methylquinoxaline‐1,4‐dioxide with cyclohexanone and dimedone in dimethylformamide in the presence of anhydrous ZnCl2 under Friedländer‐type cyclocondensation gave compounds 12‐amino‐9‐methyl‐1,2,3,4,12,12a‐hexahydroquinolino[2,3‐b]quinoxaline‐6,11‐dioxide ( 4 ), 7‐methyl‐4‐oxo‐3,4‐dihydro‐1H‐spiro[benzo[g]pteridine‐2,1′‐cyclohexane]5,10‐dioxide ( 5 ), and 12‐amino‐3,3,9‐trimethyl‐1‐oxo‐1,2,3,4,12,12a‐hexahydroquinolino[2,3‐b]quinoxaline‐6,11‐dioxide ( 6 ); (R)‐3′,3′,7‐trimethyl‐4,5′‐dioxo‐3,4‐dihydro‐1H‐spiro[benzo[g]pteridine‐2,1′‐cyclohexane]5,10‐dioxide ( 7 ) were achieved and evaluated their biological activity as antibacterial and antifungal activities and antitumor evaluation, and also, the density functional theory calculations were evaluated. 相似文献
12.
An Efficient One‐pot Synthesis of Novel Spiro Cyclic 2‐Oxindole Derivatives of Pyrimido[4,5‐b]Quinoline,Pyrido[2,3‐d:6,5‐d′]Dipyrimidine and Indeno[2′,1′:5,6]Pyrido [2,3‐d]Pyrimidine in Water
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Amr Mohamed Abdelmoniem Huwaida M. E. Hassaneen Ismail Abdelshafy Abdelhamid 《Journal of heterocyclic chemistry》2016,53(6):2084-2090
A novel and facile one‐pot synthesis of spiro cyclic 2‐oxindole derivatives of pyrimido[4,5‐b]quinoline‐4,6‐dione, pyrido[2,3‐d:6,5‐d′]dipyrimidine‐2,4,6‐trione, and indeno[2′,1′:5,6]pyrido [2,3‐d]pyrimidine employing 6‐aminothiouracil (or 6‐aminouracil), isatin, and cyclic 1,3‐diketone (e.g. 1,3‐indanedione, dimedone, or barbituric acid) has been developed. 相似文献
13.
The base promoted four-component reaction of hydrated hydrazine, dimethyl acetylenedicarboxylate, isatines and malononitrile (ethyl cycanoacetate) in ethanol afforded polysubstituted spiro[indoline-3,4‘-pyrano[2,3-c]pyrazoles] and spiro[acenaphthyl-3,4-pyrano[2,3-c]pyrazoles] 相似文献
14.
Sadif A. Shirvan Ramin Ghahremanzadeh Mojtaba Mirhosseini Moghaddam Ayoob Bazgir Amir Hassan Zarnani Mohammad Mehdi Akhondi 《Journal of heterocyclic chemistry》2012,49(4):951-954
Synthesis of spiro[indoline‐pyrazolo[4′,3′:5,6]pyrido[2,3‐d]pyrimidine]trione derivatives by a cyclo‐condensation reaction of indolin‐2‐ones, barbituric acids, and 1,3‐diphenyl‐1H‐pyrazol‐5‐amines with the ionic liquid as an effective green reaction media and in the presence of Alum as a reusable catalyst was reported. Excellent yields of products, green media, use of a reusable catalyst, and short reaction time are the main advantages of this new method. 相似文献
15.
Oleksii Y. Voskoboynik Oleksandra S. Kolomoets Inna S. Nosulenko Galina G. Berest Andrii K. Bilyi Oleksandr V. Karpenko Igor F. Belenichev Sergiy I. Kovalenko 《Journal of heterocyclic chemistry》2019,56(5):1605-1612
Previously unknown 3′‐R1‐5‐R2‐spiro[indoline‐3,6′‐[1,2,4]triazino[2,3‐c]quinazoline]‐2,2′‐(7′H)‐diones and their N‐substituted analogues were obtained via reaction of 6‐R1‐3‐(2‐aminophenyl)‐1,2,4‐triazin‐5‐ones with isatin and its substituted derivatives. It was shown that alkylation of 3′‐R1‐5‐R2‐spiro[indoline‐3,6′‐[1,2,4]triazino[2,3‐c]quinazolin]‐2,2′‐(7′H)‐diones by N‐R3‐chloroacetamides or chloroacetonitrile in the presence of а base proceeds by N‐1 atom of isatin fragment. The spectral properties (1H and 13C NMR spectra) of synthesized compounds were studied, and features of spectral patterns were discussed. The high‐effective anticonvulsant and radical scavenging agents among 3′‐R1‐5‐R2‐spiro[indoline‐3,6′‐[1,2,4]triazino[2,3‐c]quinazolin]‐2,2′(7′H)‐diones and their N‐substituted derivatives were detected. It was shown that compounds 2.2 , 2.8 , and 3.1 exceed or compete the activity of the most widely used in modern neurology drug—lamotrigine on the pentylenetetrazole‐induced seizures model. The aforementioned fact may be considered as a reason for further profound study of synthesized compounds using other pathology models. 相似文献
16.
Kamal M. Dawood 《Journal of heterocyclic chemistry》2005,42(2):221-225
Reactions of 2,3‐dihydro‐4‐oxo‐thiopyrano[2,3‐b]pyridine with aldehydes and with DMF‐DMA furnished the 3‐benzylidene and 3‐(N,N‐dimethylamino)‐methylene derivatives. The latter products afforded spiro‐pyrazolo‐3,3′‐thiopyrano[2,3‐b]pyridines and new tetra‐ and penta‐heterocyclic ring systems when treated with nitrilimines and aminoazoles, respectively. A number of the products showed high antifungal and antibacterial activities. 相似文献
17.
《应用有机金属化学》2017,31(11)
Superparamagnetic nanoparticles of modified thioglycolic acid (γ‐Fe2O3@SiO2‐SCH2CO2H) represent a new, efficient and green catalyst for the one‐pot synthesis of novel spiro[benzo[a ]benzo[6,7]chromeno[2,3‐c ]phenazine] derivatives via domino Knoevenagel–Michael–cyclization reaction of 2‐hydroxynaphthalene‐1,4‐dione, benzene‐1,2‐diamines, ninhydrin and isatin. This novel magnetic organocatalyst was easily isolated from the reaction mixture by magnetic decantation using an external magnet and reused at least six times without significant loss in its activity. The catalyst was fully characterized using various techniques. This procedure was also applied successfully for the synthesis of benzo[a ]benzo[6,7]chromeno[2,3‐c ]phenazines. 相似文献
18.
The reaction of 1H‐indol‐2,3‐diones with 1,6‐dibromohexane has resulted in the formation of new 1H‐indol‐2,3‐diones‐1,1′‐(1,6‐hexanediyl)bis in quantitative yields. These compounds have been used for the synthesis of novel [3′‐(2,3‐dimethyl‐5‐oxo‐1‐phenyl‐3‐pyrazolin‐4‐yl)spiro[3H‐indol‐3,2′‐thiazolidine]‐2,4′‐dione]‐1,1′‐(1,6‐hexanediyl)bis via bis Schiff's bases, [3‐(2,3‐dimethyl‐5‐oxo‐1‐phenyl‐3‐pyrazolin‐4‐yl) imino‐1H‐indol‐2‐one]‐1,1′‐(1,6‐hexanediyl)bis. 相似文献
19.
Mojtaba Mirhosseini Moghaddam Ayoob Bazgir Akhondi Mohammad Mehdi Ramin Ghahremanzadeh 《中国化学》2012,30(3):709-714
The combination of isatin, barbituric acid, and cyclohexane‐1,3‐dione derivatives in the presence of alum (KAl(SO4)2·12H2O) as a catalyst for 15 min was found to be a suitable and efficient method for the synthesis of spiro[chromeno[2,3‐d]pyrimidine‐5,3′‐indoline]‐tetraones. 相似文献
20.
《Journal of heterocyclic chemistry》2017,54(6):3418-3426
Structurally diverse spiroheterocycles; spiro[pyrimido[2,1‐b ]benzothiazole‐3,3′‐chromene]‐2′,4′‐dione, spiro[pyrimido[2,1‐b ]benzothiazole‐3,5′‐pyrimidine]‐2′,4′,6′‐trione, and spiro[pyrimido[2,1‐b ]benz‐thiazole‐3,2′‐cyclohexane]‐1′,3′‐dione have been synthesized by an environmentally benign, efficient, and facile one‐pot pseudo‐four component reaction of 2‐aminobenzothiazoles with aromatic aldehydes and cyclic β‐diketones in aqueous medium. The process involves hetero‐Diels–Alder cycloaddition and provides facile access to spiroheterocycles fused with potentially interesting biologically active scaffolds. The configuration of hetero‐Diels–Alder cycloadduct has been ascertained through density functional theory calculations. 相似文献