1,2,6-Oxadiazines and 1,2,6-Thiadiazines

Weintraub, Philip M.

doi:10.1016/b978-008044992-0.00807-5

Cited by 4 publications

(2 citation statements)

References 90 publications

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“…1,2,6-Thiadiazines are sulfur-nitrogen heterocycles that have broad applications . Non S-oxidized 4 H -1,2,6-thiadiazines are rare, but have uses in both the biological , and materials sciences. , Their chemistry and applications have recently been reviewed .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Chemistry of Benzo[e][1,2,6]thiadiazino[3,4-b][1,4]diazepin-10(11H)-ones and Related Ring Transformations

2021

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2-[(3,5-Dichloro-4H-1,2,6-thiadiazin-4-ylidene)amino]benzamides are cyclized to benzo[e][1,2,6]thiadiazino[3,4-b][1,4]diazepin-10(11H)-ones via (i) treatment with NaH and via (ii) Pd-catalyzed C-N coupling. The behavior of the latter toward nucleophiles and thermal, oxidative, and reductive conditions revealed unexpected transformations to 3,5-dioxo-4,5-dihydro-3H-benzo[e][1,4]diazepine-2-carbonitrile and 2-(4-substituted-1,2,5-thiadiazol-3-yl)quinazolin-4(3H)-ones.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Chemistry of Benzo[e][1,2,6]thiadiazino[3,4-b][1,4]diazepin-10(11H)-ones and Related Ring Transformations

2021

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“…The synthesis and reactivity of 1,2,6-thiadiazines has been reviewed [164]. Surprisingly, little is known on nonoxidized 4 H -1,2,6-thiadiazines.…”

Section: Synthesismentioning

confidence: 99%

Breathing Some New Life into an Old Topic: Chalcogen-Nitrogen π-Heterocycles as Electron Acceptors

et al. 2013

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Recent progress in the design, synthesis and characterization of chalcogennitrogen π-heterocycles, mostly 1,2,5-chalcogenadiazoles (chalcogen: S, Se and Te) and their fused derivatives, possessing positive electron affinity is discussed together with their use in preparation of charge-transfer complexes and radical-anion salts-candidate building blocks of molecule-based electrical and magnetic functional materials.

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Synthesis and Reactivity of 3′,5′‐Dichloro‐1H‐spiro(quinazoline‐2,4′‐[1,2,6]thiadiazin)‐4(3H)‐ones

2019

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A three‐step synthesis of 3′,5′‐dichloro‐1H‐spiro(quinazo‐line‐2,4′‐[1,2,6]thiadiazin)‐4(3H)‐ones starting from 3,4,4,5‐tetra‐chloro‐4H‐1,2,6‐thiadiazine is presented. The latter reacts with 2‐aminobenzonitriles to give 2‐[(3,5‐dichloro‐4H‐1,2,6‐thiadiazin‐4‐ylid‐ene)amino]benzonitriles, which affords, after hydration, the respective benzamides. Upon heating at reflux in EtOH or HFIP, the benzamides intramolecularly cyclize onto the thiadiazine C4 position to give 3′,5′‐dichloro‐1H‐spiro(quinazoline‐2,4′‐[1,2,6]thiadiazin)‐4(3H)‐ones. Single crystal X‐ray crystallography supports the structure of two analogues. The chloride displacement of these new spiroquinazolinones was demonstrated by Stille coupling, and by reaction with methoxide to afford both the mono and bis‐methoxy derivatives.

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1,2,6-Oxadiazines and 1,2,6-Thiadiazines

Cited by 4 publications

References 90 publications

Synthesis and Chemistry of Benzo[e][1,2,6]thiadiazino[3,4-b][1,4]diazepin-10(11H)-ones and Related Ring Transformations

Synthesis and Chemistry of Benzo[e][1,2,6]thiadiazino[3,4-b][1,4]diazepin-10(11H)-ones and Related Ring Transformations

Breathing Some New Life into an Old Topic: Chalcogen-Nitrogen π-Heterocycles as Electron Acceptors

Synthesis and Reactivity of 3′,5′‐Dichloro‐1H‐spiro(quinazoline‐2,4′‐[1,2,6]thiadiazin)‐4(3H)‐ones

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