Diels-Alder Reactions of Bicyclic 1,2,4-Triazines: The Conversion of Pyrimido[4,5-]-1,2,4-triazines to Pyrido[2,3-]pyrimidines (5-Deazapteridines)

Taylor, Edward C.; McDaniel, Keith F.; Warner, John C.

doi:10.1016/s0040-4039(00)96024-6

Cited by 21 publications

(2 citation statements)

References 5 publications

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“…In connection with the last fact it is necessary to draw particular attention to the discovery of inhibitors of reverse transcriptase HIV-1 among the pyridone derivatives [80][81][82][83][84][85][86][87][320][321][322][323][324][325]. In addition, they can serve as models of oxidation-reduction coenzymes NAD and NADF [236] and synthons for the production of analogs of folic acid [327], vitamin B6 [328], and other biologically active compounds [329][330][331][332][333][334].…”

Section: Cyclization Of Derivatives Of Pyridinechalcogenones To Annelmentioning

confidence: 99%

Synthesis and properties of 3-cyanopyridine-2(1H)-chalcogenones. Review

Литвинов¹,

Кривоколыско²,

Dyachenko³

1999

Chem Heterocycl Compd

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Section: Cyclization Of Derivatives Of Pyridinechalcogenones To Annelmentioning

confidence: 99%

Synthesis and properties of 3-cyanopyridine-2(1H)-chalcogenones. Review

Литвинов¹,

Кривоколыско²,

Dyachenko³

1999

Chem Heterocycl Compd

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“…The second one (Path B) utilized an intermolecular reaction of a triazine and a carbonyl donor [6][7]. The last one (Path C) involved a bimolecular condensation of a triazine with a guanidine or with a urea derivative [8][9][10]. These approaches either utilized a toxic reagent such as Pd(OAc) 4 or resulted in low yields (30-50%), so there was a need to develop a better preparative method for this class of compounds.…”

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confidence: 99%

An expedient synthesis of an isofervenulin analogue

Bach¹,

Jiang²,

McKenna³

et al. 2004

Journal of Heterocyclic Chem

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An efficient approach has been developed for the synthesis of an isofervenulin analogue 1 employing a one-pot condensation-substitution reaction of a chlorocarboethoxytriazine (electrophile) with a urea (nucleophile). The resulting cyclization reaction resulted in the synthesis of a pyrimido-heterocycle in good yield in either acidic or basic media. The former was assisted by utilizing trimethylsilyl chloride.

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The Retro–Diels–Alder Reaction PartII. Dienophiles with One or More Heteroatom

Rickborn

1998

Organic Reactions

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This review (Part II) is topically organized around the dienophile that is generated in a retro [4 + 2] reaction, and to the extent possible follows the principles adopted for Part I, which covers reactions in which both dienophile bonding centers are carbon atoms. The present chapter encompasses retro–Diels–Alder (rDA) reactions in which one or both of the dienophile reaction centers are heteroatoms. Any of the other atoms in the starting material (cycloadduct) may be carbon or heteroatom. Substituents on all positions are encompassed, and any bond order available to any oxidation state of an element is included, as is bonding to non‐nearest neighbor atoms (e.g., bicyclics). The reader is directed to Part I (Vol. 52) for general discussion of the rDA reaction, the features that affect rates and outcome, and the use of acids, bases, other catalysts, and scavengers. Certain subclassifications (e.g., processes proposed under MS conditions, polymer applications) of rDA reactions have been omitted from both sections; these topics are listed in the Introduction to Part I. Citations to over 100 reviews on various aspects of the rDA reaction are collected at the beginning of the References to Part I. Those that are especially pertinent to Part II will be repeated here, in the context of the particular dienophile under discussion. The decision to split the review of the rDA reaction into two parts was based on the volume of literature encountered, as outlined in the Introduction to Part I. Active literature searching was concluded for both Parts in April 1995, although occasional more recent references have been included.

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Diels-Alder Reactions of Bicyclic 1,2,4-Triazines: The Conversion of Pyrimido[4,5-]-1,2,4-triazines to Pyrido[2,3-]pyrimidines (5-Deazapteridines)

Cited by 21 publications

References 5 publications

Synthesis and properties of 3-cyanopyridine-2(1H)-chalcogenones. Review

Synthesis and properties of 3-cyanopyridine-2(1H)-chalcogenones. Review

An expedient synthesis of an isofervenulin analogue

The Retro–Diels–Alder Reaction PartII. Dienophiles with One or More Heteroatom

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