Solid‐Phase Synthesis of 1,3,5,6‐Tetra‐Substituted 3,5‐Dihydroimidazo[4,5‐<i>c</i>][1,2]Thiazin‐4(<scp>1</scp><i>H</i>)‐One 2,2‐Dioxide Derivatives

ABSTRACT The synthesis of 1,3,5,6‐tetra‐substituted 3,5‐dihydroimidazo[4,5‐ c ][1,2]thiazin‐4(1 H )‐one 2,2‐dioxide derivatives was optimized through solid‐phase synthesis. Synthetic strategies such as Merrifield resin, Thorpe‐Ziegler reaction, Mitsunobu reaction, intramolecular cyclization, and desulfonative nucleophilic substitution were employed to synthesize a total of 31 derivatives. The synthesis showed high yields of 72%–87% per step over 8 steps, resulting in an overall yield of 7%–33%, thereby developing an efficient synthetic route for the derivatives.

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Publication Details

Journal
Journal of Heterocyclic Chemistry
Published
2025-07-30
DOI
https://doi.org/10.1002/jhet.70045
Primary Topic
Quinazolinone synthesis and applications
Type
article
Field-Weighted Citation Impact
0.00

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article

Solid‐Phase Synthesis of 1,3,5,6‐Tetra‐Substituted 3,5‐Dihydroimidazo[4,5‐c][1,2]Thiazin‐4(1H)‐One 2,2‐Dioxide Derivatives

Jimin Moon, Taeho Lee, Hyo‐Jin Lee, Sohee Kim
Journal of Heterocyclic Chemistry
Quinazolinone synthesis and applications
article

Solid‐Phase Synthesis of 1,3,5,6‐Tetra‐Substituted 3,5‐Dihydroimidazo[4,5‐c][1,2]Thiazin‐4(1H)‐One 2,2‐Dioxide Derivatives

Jimin Moon, Taeho Lee, Hyo‐Jin Lee, Sohee Kim
article en

Abstract

ABSTRACT The synthesis of 1,3,5,6‐tetra‐substituted 3,5‐dihydroimidazo[4,5‐ c ][1,2]thiazin‐4(1 H )‐one 2,2‐dioxide derivatives was optimized through solid‐phase synthesis. Synthetic strategies such as Merrifield resin, Thorpe‐Ziegler reaction, Mitsunobu reaction, intramolecular cyclization, and desulfonative nucleophilic substitution were employed to synthesize a total of 31 derivatives. The synthesis showed high yields of 72%–87% per step over 8 steps, resulting in an overall yield of 7%–33%, thereby developing an efficient synthetic route for the derivatives.

Journal of Heterocyclic ChemistryVol. 62(9)
Kyungpook National University (KR)
Kyungpook National University
Openalex Percentile: Top 86%
Quinazolinone synthesis and applications
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