scholarly journals Synthesis of Dispiro[Indeno[1,2-b]Quinoxaline-11,3′-Pyrrolizine-2′,2″-[1,3] Thiazolo[3,2-a]Pyrimidine Via Cycloaddition Reactions

2018 ◽  
Vol 42 (9) ◽  
pp. 453-455 ◽  
Author(s):  
Demin Ren ◽  
Xiaolian Hu ◽  
Yulin Huang ◽  
Xiaofang Li
Keyword(s):  
Cycloaddition Reaction ◽  
Crystallographic Analysis ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
X Ray

The 1,3-dipolar cycloaddition reaction of ethyl 5-aryl-2-(2-methoxy-2-oxoethylidene)-7-methyl-3-oxo-2,3-dihydro-5 H-[1,3]thiazolo[3,2- a] pyrimidine-6-carboxylate and azomethine ylide, which was generated in situ by the reaction of 11 H-indeno[1,2- b]quinoxalin-11-one and L-proline, afforded novel 6″ethyl 1′-methyl 5″aryl-7″methyl-3″oxo-5’,6’,7’,7a′-tetrahydro-1' H,3″ H,5″ H-dispiro[indeno[1,2- b]quinoxaline-11, 3 ‘-pyrrolizine-2’,2″-[1,3]thiazolo[3,2- a]pyrimidine-1’,6″-dicarboxylates in good yields. The structures of all the products were characterised thoroughly by NMR, IR and HRMS together with X-ray crystallographic analysis.

Synthesis of Spiro[Pyrrolo[2,1-b][1,3]Benzothiazole-3,2′-[1,3]Thiazolo[3,2-a] Pyrimidine] via Cycloaddition Reactions

2018 ◽  
Vol 42 (5) ◽  
pp. 260-263 ◽  
Author(s):  
Qing Zeng ◽  
Demin Ren ◽  
Xingliang Fu ◽  
Xiaofang Li
Keyword(s):  
Cycloaddition Reaction ◽  
Crystallographic Analysis ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
X Ray

The 1,3-dipolar cycloaddition reaction of ethyl-5-aryl-2-[( Z)-2-methoxy-2-oxoethylidene]-7-methyl-3-oxo-3,5-dihydro-2 H-thiazolo[3,2- a] pyrimidine-6-carboxylates and azomethine ylide, which was generated in situ by the reaction of N-4-methoxyphenacylbenzothiazolium bromides and triethylamine, yielded novel 6′-ethyl-2-methyl-5′-aryl-1-(4-methoxybenzoyl)-7-methyl-3′-oxo-1,2-dihydro-5 H-spiro[pyrrolo[2,1- b][1,3]benzothiazole-3,2′-[1,3]thiazolo[3,2- a]pyrimidine]-2,6′-dicarboxylates in moderate yields. The structures of all of the products were characterised by NMR, IR, HRMS spectrometry, together with X-ray crystallographic analysis.

scholarly journals Diastereoselective Synthesis of Spiro[Pyrrolo[2,1-B][1,3] Benzothiazole-3,5′-[1,3]Thiazolo[3,2-B][1,2,4]Triazol]-6′-Ones via Cycloaddition Reaction of Benzothiazolium Salts

2018 ◽  
Vol 42 (7) ◽  
pp. 371-373 ◽  
Author(s):  
Qing Zeng ◽  
Demin Ren ◽  
Yulin Huang ◽  
Xinliang Fu ◽  
Xiaofang Li
Keyword(s):  
Cycloaddition Reaction ◽  
Crystallographic Analysis ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
X Ray

The 1,3-dipolar cycloaddition reaction of (Z)-5-arylidene[1,3]thiazolo[3,2-b][1,2,4]triazol-6(5H)-one and azomethine ylide, which was generated in situ by the reaction of N-4-methoxyphenacylbenzothiazolium bromides and triethylamine, afforded novel 2-(aryl)-1-(4-methoxybenzoyl)-1,2-dihydrospiro[pyrrolo[2,1-b][1,3]benzothiazole-3,5′-[1,3]thiazolo[3,2-b][1,2,4]triazol]-6′-ones in moderate yields. The structures of all the products were characterised thoroughly by NMR, IR and HRMS spectroscopy together with X-ray crystallographic analysis.

scholarly journals Regio- and Stereoselectivity in the 1,3-Dipolar Cycloaddition Reactions of Isoquinolinium Ylides with Cyclopenta[a]acenaphthylen-8-ones

Synlett ◽  
2020 ◽  
Vol 31 (17) ◽  
pp. 1691-1695
Author(s):  
Issa Yavari ◽  
Parisa Ravaghi ◽  
Maryam Safaei ◽  
Jasmine Kayanian
Keyword(s):  
Dft Calculations ◽  
Cycloaddition Reaction ◽  
Crystallographic Analysis ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Diastereoselective Synthesis ◽  
X Ray

AbstractA convenient regio- and diastereoselective synthesis of functionalized 5a,5b-dihydro-5H,13H-naphtho[1′′,8′′:4′,5′,6′]pentaleno[1′:3,4]pyrrolo[2,1-a]isoquinolin-5-ones via 1,3-dipolar cycloaddition reaction of 8H-cyclopenta[a]acenaphthylen-8-ones with carbonyl-stabilized isoquinolinium N-ylides, is described. Based on DFT calculations at b3lyp/6-311+g(d,p) level of theory, a nonconcerted mechanism is proposed to explain the regioselectivity of this reaction. The structure of a typical product was confirmed by X-ray crystallographic analysis.

Synthesis of novel dispiro[indazole-5,3′-pyrrolidine-2′,3″-indole] derivatives via 1,3-dipolar cycloaddition of azomethine ylide

2017 ◽  
Vol 41 (7) ◽  
pp. 427-429
Author(s):  
Demin Ren ◽  
Guoqiang Kuang ◽  
Xiaolian Hu ◽  
Xiaofang Li
Keyword(s):  
Crystallographic Analysis ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Indole Derivatives ◽  
X Ray

The 1,3-dipolar cycloaddition of azomethine ylide, generated in situ from isatin and sarcosine, to 5-arylmethylidene-1-phenyl-6,7-dihydro-1 H-indazol-4(5 H)-ones afforded novel 1′-methyl-4′-aryl-1-phenyl-6,7-dihydrodispiro[indazole-5,3′-pyrrolidine-2′,3″-indole]-2″,4(1 H,1″ H)-diones in moderate yields. The structures of all the products were characterised thoroughly by NMR, IR, HRMS, together with X-ray crystallographic analysis.

A Convenient Synthesis of Fused Tetrahydroazocines from Acenaphthylene-1,2-dione, Proline, and Acetylenic Esters

Synlett ◽  
2017 ◽  
Vol 29 (05) ◽  
pp. 635-639 ◽  
Author(s):  
Issa Yavari ◽  
Leila Baoosi ◽  
Mohammad Halvagar
Keyword(s):  
Cycloaddition Reaction ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
X Ray Diffraction ◽  
Acetylenic Esters ◽  
X Ray ◽  
Convenient Synthesis ◽  
Boat Form ◽  
Twist Boat

A synthesis of dialkyl (12E,14E)-7-oxo-10,11-dihydro-7H,9H-azocino[2,1-a]benzo[de]isoquinoline-13,14-dicarboxylates through a 1,3-dipolar cycloaddition reaction of azomethine ylides, generated in situ from proline and acenaphthylene-1,2-dione, with dialkyl acetylenedicarboxylates is described. According to the X-ray diffraction data, the tetrahydroazocine ring has a rigid twist-boat form with approximate local C2 symmetry.

1,3-Dipolar cycloaddition reactions of phthalic anhydrides with an azomethine ylide

2015 ◽  
Vol 2 (6) ◽  
pp. 705-712 ◽  
Author(s):  
Hugo Santos ◽  
Amy Distiller ◽  
Asha M. D'Souza ◽  
Quentin Arnoux ◽  
Jonathan M. White ◽  
...  
Keyword(s):  
Ring Opening ◽  
Cycloaddition Reaction ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Ring Opening Reaction ◽  
Phthalic Anhydrides

A series of phthalic anhydrides underwent a 1,3-dipolar cycloaddition reaction with N-benzylazomethine ylide to produce unstable spiro(isobenzofuran-1,5′-oxazolidin)-3-ones, which underwent a subsequent reductive ring-opening reaction to afford 1(3H)-isobenzofuranones.

scholarly journals Competitive 1,3-Dipolar Cycloaddition Reactions of an Azomethine Ylide with Aromatic and Carbonyl Groups of Nitro-Substituted Isatoic Anhydrides

2018 ◽  
Vol 71 (9) ◽  
pp. 690 ◽  
Author(s):  
Asha M. D'Souza ◽  
Daniel J. Rivinoja ◽  
Roger J. Mulder ◽  
Jonathan M. White ◽  
Adam G. Meyer ◽  
...  
Keyword(s):  
Carbonyl Group ◽  
Aromatic Ring ◽  
Addition Reaction ◽  
Cycloaddition Reaction ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Carbonyl Groups ◽  
Isatoic Anhydride

A study of the reactivity of a non-stabilised azomethine ylide, derived from N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine, with nitro-substituted isatoic anhydrides was undertaken. N-Methyl-4-nitroisatoic anhydride underwent a 1,3-dipolar cycloaddition reaction exclusively at the isatoic anhydride C1-carbonyl group, followed by decarboxylative rearrangement to yield a benzo-1,3-diazepin-5-one derivative. In contrast, N-methyl-5-nitroisatoic anhydride underwent competing cycloaddition processes to the isatoic anhydride C1-carbonyl group and to the nitro-substituted aromatic ring. The dearomative addition reaction resulted in the formation of novel tetracyclic products.

Synthesis of 5-Aryloxazolidines via 1,3-Dipolar Cycloaddition Reaction of a Non-Stabilized Azomethine Ylide with Aromatic Aldehydes

2007 ◽  
Vol 60 (12) ◽  
pp. 898 ◽  
Author(s):  
John H. Ryan ◽  
Nadia Spiccia ◽  
Leon S.-M. Wong ◽  
Andrew B. Holmes
Keyword(s):  
Trifluoroacetic Acid ◽  
Cycloaddition Reaction ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition

The 1,3-dipolar cycloaddition reaction of a non-stabilized azomethine ylide 4a, formed in situ from N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine 5 and a catalytic amount of trifluoroacetic acid, with aromatic aldehydes 3 gives rise to N-benzyl-5-aryloxazolidines 1. Under these conditions, 4-hydroxybenzaldehyde 3p undergoes two-fold addition of azomethine ylide 4a to afford bis adduct 11.

Synthesis of spiro[cyclopent-2/3-ene-1,2′-[1,3]thiazolo[3,2-a] pyrimidine] derivatives via 1,3-dipolar cycloaddition reaction of ethyl buta-2,3-dienoate

2018 ◽  
Vol 42 (12) ◽  
pp. 631-635 ◽  
Author(s):  
Demin Ren ◽  
Ye Tang ◽  
Xianyong Yu ◽  
Yulin Huang ◽  
Xiaofang Li
Keyword(s):  
Cycloaddition Reaction ◽  
Crystallographic Analysis ◽  
Dipolar Cycloaddition ◽  
Pyrimidine Derivatives ◽  
X Ray

The 1,3-dipolar cycloaddition reaction of ethyl (2Z)-5-aryl-2-(2-methoxy-2-oxoethylidene)-7-methyl-2,3-dihydro-5H-thiazolo[3,2-a] pyrimidine-6-carboxylate and ethyl buta-2,3-dienoate catalysed by triphenylphosphine afforded novel spiro[cyclopent-2-ene-1,2′-[1,3] thiazolo[3,2-a]pyrimidine] and spiro[cyclopent-3-ene-1,2′-[1,3]thiazolo[3,2-a]pyrimidine] derivatives in moderate yields. The structures of all the products were characterised thoroughly by NMR, IR and HRMS together with X-ray crystallographic analysis.

scholarly journals Indolizines and pyrrolo[1,2-c]pyrimidines decorated with a pyrimidine and a pyridine unit respectively

2015 ◽  
Vol 11 ◽  
pp. 1079-1088 ◽  
Author(s):  
Marcel Mirel Popa ◽  
Emilian Georgescu ◽  
Mino R Caira ◽  
Florentina Georgescu ◽  
Constantin Draghici ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
Nitrogen Atom ◽  
Steric Hindrance ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Pyridine Nitrogen Atom ◽  
Structural Isomers ◽  
X Ray ◽  
Pyridine Nitrogen

The three possible structural isomers of 4-(pyridyl)pyrimidine were employed for the synthesis of new pyrrolo[1,2-c]pyrimidines and new indolizines, by 1,3-dipolar cycloaddition reaction of their corresponding N-ylides generated in situ from their corresponding cycloimmonium bromides. In the case of 4-(3-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine the quaternization reactions occur as expected at the pyridine nitrogen atom leading to pyridinium bromides and consequently to new indolizines via the corresponding pyridinium N-ylides. However, in the case of 4-(2-pyridyl)pyrimidine the steric hindrance directs the reaction to the pyrimidinium N-ylides and, subsequently, to the formation of the pyrrolo[1,2-c]pyrimidines. The new pyrrolo[1,2-c]pyrimidines and the new indolizines were structurally characterized through NMR spectroscopy. The X-ray structures of two of the starting materials, 4-(2-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine, are also reported.

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