Fluorine control of regioselectivity in photocycloaddition reactions. The direct functionalization of uracil via a novel 1,4-fragmentation

Wexler, Allan; Swenton, John S.

doi:10.1021/ja00422a066

Cited by 24 publications

(5 citation statements)

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“…Depending on the nature of the substituents, their location, and reaction conditions, the pyrimidodiazepines were converted into either pyrido [2,3- d ]pyrimidines, pyrazolo [3,4- d ]pyrimidines or a pyrimido [4,5- c ]pyridazine. [ 14 ] But on heating pyrimidodiazepine 3a with 1 N HCl above 90°C for about 2 h, we observed the formation of corresponding pyrazolo [3,4-d]pyrimidines in poor yields (15%). To enhance the yield further, increase of reaction time also did not give any fruitful results rather decomposition of starting material occurred.…”

Section: Resultsmentioning

confidence: 96%

“…[ 9 - 12 ] There have been reports for direct functionalisation of uracil using the C5-C6 double bond via thermolytic[ 13 ] and photocycloaddition reactions. [ 14 , 15 ] The heteroannulation of uracils usually require either forcing conditions[ 16 , 17 ] or relatively longer synthetic pathways. [ 18 ] Also, pyrazolo [3,4-d]pyrimidines are a class of naturally occurring fused uracils that possess a wide range of biological activity.…”

Section: Introductionmentioning

confidence: 99%

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One-pot synthesis of novel 1H-pyrimido[4,5-c][1,2]diazepines and pyrazolo[3,4-d]pyrimidines

Prajapati¹,

Baruah²,

Gogoi³

et al. 2006

Beilstein J. Org. Chem.

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Section: Resultsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

One-pot synthesis of novel 1H-pyrimido[4,5-c][1,2]diazepines and pyrazolo[3,4-d]pyrimidines

Prajapati¹,

Baruah²,

Gogoi³

et al. 2006

Beilstein J. Org. Chem.

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“…Nj-deazafolate (2). There have been reports for direct functionalization of 6-aminouracils using the C5-C6 double bond via different techniques (9)(10)(11). The synthetic exploitation of the nucleophilic double bond of uracil is an important undeveloped filed in view of a great variety of potential products (6)(7)(8).…”

Section: Introductionmentioning

confidence: 99%

A CONVENIENT ONE POT SYNTHESIS OF PYRIDO[2,3-d]- PYRIMIDINES AND PYRIMIDO[2,3-c]PYRIMIDINES (N5-DEAZAPETRINS)

Mekheimer¹,

El‐Nabi²,

Abd-Elhameed³

et al. 2000

Heterocyclic Communications

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“…[193][194][195][196] Later efforts also considered photodimerization of 5-FU as a useful synthetic approach to substituted pyrimidines and novel bicyclic nucleosides (Scheme 4.2b). [197][198][199] The photophysics behind the dimerization [200][201] and cleavage 202 of fluorouracil dimers and cycloadducts was also studied as interest in 5-FU was maintained through the last few Continued efforts by the group moved from the original backbone to a polymethacrylatebased block copolymer, wherein one block contained alkyl-ester side chains to produce a largely hydrophobic region of the polymer, the other block bearing side chains appended with the 4-methylcoumarin moiety, drastically increasing the number of available binding sites for the API (Scheme 4.3). 204 The resulting polymer formed micelles in a water/THF co-solvent system and was conjugated to 5-FU under long-wave UV.…”

Section: Discussionmentioning

confidence: 99%

“…We note that UV-irradiation of 5-FU in solution produces photodimers only in the presence of a sensitizer, 196 while CPRs of 5-FU in solution are quite limited (e.g. coumarin) [197][198][199] yet are gaining interest in drug delivery. 202,204 Our goal to form a solid 227 with a photoreactive API such as 5-FU would also, thus, provide a unique entry to pharmaceutical cocrystals 228 wherein the covalentbond-forming photoreaction may be useful for pharmaceutical applications.…”

Section: Chapter Overviewmentioning

confidence: 99%

Explorations in crystal engineering

Duncan¹

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Explorations in crystal engineering : supramolecular templates, Explorations in crystal engineering : supramolecular templates, helical assemblies, pharmaceutical reactivity, and applications to helical assemblies, pharmaceutical reactivity, and applications to radio-imaging radio-imaging ____________________________________________ Michael Schultzii To Krista and Jasmine, Sasha, Tayla, Kenzie, and my loving parents iii I do not know what I may appear to the world, but to myself I seem to have been only like a boy playing on the sea-shore, and diverting myself in now and then finding a smoother pebble or a prettier shell than ordinary, whilst the great ocean of truth lay all undiscovered before me. Isaac Newtoniv ACKNOWLEDGEMENTSThere are a number of people I owe my success to, and I would like to take this space to offer them the most sincere love and gratitude for all the things they've done for me. Above all I must thank my research advisor, Professor Leonard R. MacGillivray. He has been a constant source of guidance in navigating the trials of earning a graduate degree. His mentoring has helped me hone my skills as a scientist and, looking back over the past six years, I can hardly believe how much my approach to research and problem solving has changed thanks to his influence. My gratitude to him is never-ending and I will continue to build on the foundation he has helped me establish as I continue in my career. Of course, I must thank the members of the MacGillivray research group, past and present: Beth, and Celymar. The insight, collaboration, and companionship they provided over the years will be some of the fondest memories from my time at Iowa. Also, I would like to thank the undergrads that worked with me, Roxie, Shawna, Kyle, Carlson, and Jeremy, who assisted me in my dissertation work. I am indebted to Dr. Dale Swenson for the enumerable times I bugged him in his office for help with crystallography. Dale never turned me away when I needed help working on a structure or needed advice on how to present and justify less-than-perfect quality data. I owe my knowledge and skill in X-ray crystallography to him and his generous teaching mentality. vi ABSTRACT Crystal engineering is a rapidly developing area of research with goals aimed at designing molecular solids with desired physical and chemical properties. By utilizing reliable intermolecular interactions, the principles of supramolecular chemistry are exploited in the solid state in order to achieve favorable arrangements of molecules in a crystal lattice. We have applied crystal engineering strategies to further develop the strategy of template-directed reactivity in the solid state. An evaluation of catechol, a regioisomer of the commonly used resorcinol template, was performed. Co-crystallization of the template candidate with a bis-pyridyl olefin produced a discrete self-assembled architecture wherein hydrogen-bonded dimers of catechol pre-organize the olefins for a[2+2] photodimerization in the solid state. The dimerization was determined to pro...

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Fluorine control of regioselectivity in photocycloaddition reactions. The direct functionalization of uracil via a novel 1,4-fragmentation

Cited by 24 publications

References 3 publications

One-pot synthesis of novel 1H-pyrimido[4,5-c][1,2]diazepines and pyrazolo[3,4-d]pyrimidines

One-pot synthesis of novel 1H-pyrimido[4,5-c][1,2]diazepines and pyrazolo[3,4-d]pyrimidines

A CONVENIENT ONE POT SYNTHESIS OF PYRIDO[2,3-d]- PYRIMIDINES AND PYRIMIDO[2,3-c]PYRIMIDINES (N5-DEAZAPETRINS)

Explorations in crystal engineering

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