Preparation of pyrimido[2,1-a]phthalazines and an aminopyrimido[2,1-a]isoindole by retro Diels–Alder reaction

Sohár, Pàl; Miklós, Ferenc; Csámpai, Antal; Stájer, Géza

doi:10.1039/b005008n

Cited by 17 publications

(2 citation statements)

References 15 publications

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“…From aminonorbornane/eneamino acid hydrazides (64) with 2-aroylbenzoic acid, fused-skeleton heteropentacycles 105 were prepared (Scheme 29) [77]. The reactions of hydrazides with cyclohexane oxoacids furnished methanohexahydroquinazolino[2,3-a]-phthalazines (106).…”

Section: Scheme 28mentioning

confidence: 99%

Chemistry of Norbornane/ene and Heteronorbornane/ene β-Amino Acids

Csende¹,

Fülöp²,

Stájer

2008

COS

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Section: Scheme 28mentioning

confidence: 99%

Chemistry of Norbornane/ene and Heteronorbornane/ene β-Amino Acids

Csende¹,

Fülöp²,

Stájer

2008

COS

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“…At increased temperatures, the adduct degrades to reform a furan and maleimide. The Diels–Alder reaction has been used to prepare many novel and difficult to achieve multifunctional polymer networks 4–14. An exhaustive recent review from Gandini15 summarizes the work to date in the development and characterization of Diels–Alder polymers.…”

Section: Introductionmentioning

confidence: 99%

Reaction Kinetics and Thermodynamic Aspects of Thermoreversibly Cross‐Linked Polymer Networks

Peterson¹,

Palmese²

2013

Macro Chemistry & Physics

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The Diels-Alder reaction of furan and maleimide is used to prepare reversibly cross-linking polymer gels consisting of furan-bearing polymer chains and bismaleimides. The roles of chain length, stoichiometry, and concentration on gelation kinetics and other properties are evaluated. Additionally, kinetics of the Diels-Alder reactions in the gelling system are compared with the kinetics of small molecule systems. By combining spectroscopic and rheological techniques, a mechanochemical analysis is performed. reaction particularly desirable for the development of multi functional polymer networks.A polymer network is defi ned as a polymeric system in which the mer units are connected such that numerous paths exist through the macromolecule. Cross-linked networks are desirable because of their mechanical properties, thermal stability, and insolubility in solvents. Once cross-linked, a traditional polymer network cannot return to a moldable state. However, when cross-links are formed with Diels-Alder bonds, the resulting material can be remolded and mended at increased temperatures. [16][17][18][19] One interesting result of incorporating thermoreversible linkages is that chains within the system can diffuse and stress can relax, allowing for creep of the cross-linked network. [ 20 ] Thermoreversible bonds have also been used to create healable macromolecular systems. [ 16 , 21-26 ] Materials that can repair cracks and recover from mechanical failure are desirable. Because remendable materials both repair and prevent the propagation of microcracks, they offer the potential for increased durability, safety, and cost efficiency for many applications. Numerous examples are given in the literature of polymeric systems containing thermoreversible bonds can heal upon application of heat. [ 15 , 16 , 21 , 27-29 ] We have previously demonstrated that reversibly cross-linking gels can be incorporated within

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Preparation of 9-Amino-1,9-diazatricyclo[6.4.0.04,8]dodecane-2,10-dione by a Retro-Diels−Alder Reaction

et al. 2001

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Treatment of di-endo-or di-exo-3-aminobicyclo[2.2.1]hept-5ene-2-carbohydrazides (1a and 1b) with ethyl 2-(2-oxocyclopentyl)acetate (2) yields norbornene-condensed 9-amino-1,9-diazatricyclo[6.4.0.0 4,8 ]dodecane-2,10-diones 3a and 3b, the condensed bis(lactams) 4a and 4b and (from 1b and 2) Results and DiscussionRefluxing of di-endo-or di-exo-3-aminobicyclo-[2.2.1]hept-5-ene-2-carbohydrazides (1a/1b) with ethyl 2-(2oxocyclopentyl)acetate (2) in toluene and in the presence of PTSA as catalyst yields a mixture of norbornene-condensed [a]

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Preparation of pyrimido[2,1-a]phthalazines and an aminopyrimido[2,1-a]isoindole by retro Diels–Alder reaction

Cited by 17 publications

References 15 publications

Chemistry of Norbornane/ene and Heteronorbornane/ene β-Amino Acids

Chemistry of Norbornane/ene and Heteronorbornane/ene β-Amino Acids

Reaction Kinetics and Thermodynamic Aspects of Thermoreversibly Cross‐Linked Polymer Networks

Preparation of 9-Amino-1,9-diazatricyclo[6.4.0.04,8]dodecane-2,10-dione by a Retro-Diels−Alder Reaction

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Preparation of pyrimido[2,1-a]phthalazines and an aminopyrimido[2,1-a]isoindole by retro Diels–Alder reaction

Cited by 17 publications

References 15 publications

Chemistry of Norbornane/ene and Heteronorbornane/ene &#946;-Amino Acids

Chemistry of Norbornane/ene and Heteronorbornane/ene &#946;-Amino Acids

Reaction Kinetics and Thermodynamic Aspects of Thermoreversibly Cross‐Linked Polymer Networks

Preparation of 9-Amino-1,9-diazatricyclo[6.4.0.04,8]dodecane-2,10-dione by a Retro-Diels−Alder Reaction

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Chemistry of Norbornane/ene and Heteronorbornane/ene β-Amino Acids

Chemistry of Norbornane/ene and Heteronorbornane/ene β-Amino Acids