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Leveraging Azides in the Synthesis of Cyclobutenes and the Conversion of Arenes to Pyridines.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Leveraging Azides in the Synthesis of Cyclobutenes and the Conversion of Arenes to Pyridines./
Author:	Patel, Sajan.
Description:	1 online resource (327 pages)
Notes:	Source: Dissertations Abstracts International, Volume: 84-10, Section: B.
Contained By:	Dissertations Abstracts International84-10B.
Subject:	By products. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=30363159click for full text (PQDT)
ISBN:	9798377682554

Leveraging Azides in the Synthesis of Cyclobutenes and the Conversion of Arenes to Pyridines.
Patel, Sajan.

Leveraging Azides in the Synthesis of Cyclobutenes and the Conversion of Arenes to Pyridines. - 1 online resource (327 pages)

Source: Dissertations Abstracts International, Volume: 84-10, Section: B.

Thesis (Ph.D.)--Stanford University, 2023.

Includes bibliographical references

Four-membered rings are rapidly becoming sought-after scaffolds in pharmaceuticals due to their rigid structure and well-defined exit vectors. Towards this goal, we developed a method to enantioselectively form cyclobutenes from simple olefins and N-sulfonyl-1,2,3-triazoles. While these triazoles are known to act as diazo precursors via ring-chain tautomerization, we recognized them as vicinal dicarbene equivalents. Thus, alkynes are reacted in [3+2] cycloadditions with azides to form triazoles, which are then reacted with alkenes in a formal [2+2] cycloaddition. A host of enantioenriched cyclobutenes were synthesized, several of which were carried on to assemble the carbon skeletons of several natural products.The ability to selectively delete, insert, or exchange atoms in the core scaffolds of molecules is of fundamental interest to synthetic chemists and could be of great use to medicinal chemists seeking to rapidly modulate the parameters of lead compounds. Though atom deletions and insertions have garnered much interest in the form of ring contractions and expansions, atom exchanges have seen considerably less development. One notable exchange that has eluded chemists is the conversion of benzene to pyridine, which is of interest due to the "necessary nitrogen atom" effect, which describes the enhancement of key pharmacological properties when an arene in a lead compound was replaced with a pyridine. To this end, we found that azides serve as effective nitrene precursors to engage arenes in a C to N atom exchange sequence featuring nitrogen atom insertion and carbon atom deletion.

Electronic reproduction.
Ann Arbor, Mich. :
ProQuest,
2023

Mode of access: World Wide Web

ISBN: 9798377682554Subjects--Topical Terms:

3564729
By products.
Index Terms--Genre/Form:

542853
Electronic books.

Leveraging Azides in the Synthesis of Cyclobutenes and the Conversion of Arenes to Pyridines.
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100 1 $a Patel, Sajan. $3 3703732
245 1 0 $a Leveraging Azides in the Synthesis of Cyclobutenes and the Conversion of Arenes to Pyridines.
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300 $a 1 online resource (327 pages)
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500 $a Source: Dissertations Abstracts International, Volume: 84-10, Section: B.
500 $a Advisor: du Bois, Justin;Xia, Yan;Burns, Noah.
502 $a Thesis (Ph.D.)--Stanford University, 2023.
504 $a Includes bibliographical references
520 $a Four-membered rings are rapidly becoming sought-after scaffolds in pharmaceuticals due to their rigid structure and well-defined exit vectors. Towards this goal, we developed a method to enantioselectively form cyclobutenes from simple olefins and N-sulfonyl-1,2,3-triazoles. While these triazoles are known to act as diazo precursors via ring-chain tautomerization, we recognized them as vicinal dicarbene equivalents. Thus, alkynes are reacted in [3+2] cycloadditions with azides to form triazoles, which are then reacted with alkenes in a formal [2+2] cycloaddition. A host of enantioenriched cyclobutenes were synthesized, several of which were carried on to assemble the carbon skeletons of several natural products.The ability to selectively delete, insert, or exchange atoms in the core scaffolds of molecules is of fundamental interest to synthetic chemists and could be of great use to medicinal chemists seeking to rapidly modulate the parameters of lead compounds. Though atom deletions and insertions have garnered much interest in the form of ring contractions and expansions, atom exchanges have seen considerably less development. One notable exchange that has eluded chemists is the conversion of benzene to pyridine, which is of interest due to the "necessary nitrogen atom" effect, which describes the enhancement of key pharmacological properties when an arene in a lead compound was replaced with a pyridine. To this end, we found that azides serve as effective nitrene precursors to engage arenes in a C to N atom exchange sequence featuring nitrogen atom insertion and carbon atom deletion.
533 $a Electronic reproduction. $b Ann Arbor, Mich. : $c ProQuest, $d 2023
538 $a Mode of access: World Wide Web
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650 4 $a Hydrocarbons. $3 697428
650 4 $a Reagents. $3 3683752
650 4 $a Carbon. $3 604057
650 4 $a Styrene. $3 3703733
650 4 $a Azide. $3 3703734
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650 4 $a Catalysis. $3 560465
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650 4 $a Organic chemistry. $3 523952
650 4 $a Chemical synthesis. $3 3558072
650 4 $a Nitrogen. $3 1314426
650 4 $a Pharmaceutical sciences. $3 3173021
655 7 $a Electronic books. $2 lcsh $3 542853
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773 0 $t Dissertations Abstracts International $g 84-10B.
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=30363159 $z click for full text (PQDT)