The place of dibenzo[<i>b,f</i>]thiepin derivatives in medicinal chemistry: Structures and activities

Protiva, M.

doi:10.1002/jhet.5570330301

Cited by 13 publications

(3 citation statements)

References 195 publications

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“…Benzannulation of the thiepine ring on both sides results in the thermally robust dibenzo[ b , f ]thiepines, which are of interest for their potent biological activity, illustrated by the psychosedative and antipsychotic properties of zotepine ( 18 ; Fig. 2 ) [ 76 – 80 ].…”

Section: Reviewmentioning

confidence: 99%

Valence isomerization of cyclohepta-1,3,5-triene and its heteroelement analogues

Jansen¹,

Slootweg²,

Lammertsma³

2011

Beilstein J. Org. Chem.

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Section: Reviewmentioning

confidence: 99%

Valence isomerization of cyclohepta-1,3,5-triene and its heteroelement analogues

Jansen¹,

Slootweg²,

Lammertsma³

2011

Beilstein J. Org. Chem.

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“…Earlier studies on the chemistry of thiepines and thiepanes have been reviewed [18,19] and, more recently, these heterocycles have been described in Houben-Weyls Science of Synthesis [20]. A review of dibenzo [b,f ]thiepine has also been published [21]. In addition to these general surveys, annual accounts on seven-membered heterocyclic ring systems are given in Progress in Heterocyclic Chemistry [22].…”

Section: Introductionmentioning

confidence: 99%

Seven‐Membered Heterocycles: Azepines, Benzo Derivatives and Related Systems

Vaquero

Cuadro

Herradón

2011

Modern Heterocyclic Chemistry

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The replacement of a carbon atom by a heteroatom in a seven-membered carbocycle leads to the corresponding seven-membered heterocyclic ring system. Different types of heterocycles can be formed depending on the nature of the carbocycle. In a cycloheptatriene the replacement can involve any of the six sp 2 hybridized carbons or the sp 3 carbon atom, whereas in cycloheptane all carbon atoms are equivalent and replacement affords exclusively the fully saturated heterocyclic systems. Partially saturated seven-membered heterocycles can be viewed as derivatives or related systems of these two main seven-membered heterocyclic units arising from carbon replacement in cycloheptatriene and in cycloheptane. Replacement of the sp 3 hybridized carbon atom in cycloheptatriene by a nitrogen leads to an azacycloheptatriene known as 1H-azepine (1) and the corresponding 2H-, 3H-, and 4H-azepines (2-4) are the tautomeric forms generated by the replacement of the sp 2 carbons. 1H-Azepine is an unstable red oil that is prone to rearrange to the also unstable 3H-azepine in the presence of acids and bases. However, this tautomer seems to be more stable than both 4H-and 2H-azepine. The structures related to 1H-azepine that bear an oxygen or sulfur atom are known as oxepine (5) and thiepine (6) (thiepin is favored by Chemical Abstracts Service). Oxepine is much more stable than thiepine and has been synthesized, isolated, and characterized at room temperature while thiepine has not been detected to date. Stable monocyclic thiepines were prepared and characterized in the 1980s. Azepines, oxepines, and thiepines that are constrained to planar or almost planar conformations should be antiaromatic molecules with negative resonance energy and, as a consequence, these compounds are unknown.The fully saturated seven-membered heterocycle containing one nitrogen is azepane (7) (hexahydroazepine or perhydroazepine); the oxygen and sulfur analogues are known as oxepane (8) and thiepane (9). All of these compounds are stable and show typical behavior of secondary amine, ether and thioether, respectively. TwoModern Heterocyclic Chemistry, First Edition. Edited

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“…Derivatives of the thiepin ring system ( 1 ) (Figure ) have been intensely studied over the years, with particular emphasis on aspects such as pharmacological properties, structure, and aromaticity. – Likewise, the structurally related 1-metallacycloheptatrienes incorporating the elements silicon, germanium, selenium, or tellurium have also received certain treatment. In particular, the 1-silacyclohepta-2,4,6-triene (silepin) 2 and related structures featuring the 1-silacyclohepta-2,4,6-triene ring system have been subjected to detailed investigations, resulting in several synthetic approaches, – as well as deeper understanding of their properties, ,,,,– but only relatively few studies have been devoted to the parent ring system 3 , and other 1-germacyclohepta-2,4,6-trienes, – , or derivatives of 1-selenacyclohepta-2,4,6-triene ( 4 ). ,,, Despite all progress in this area, there is still need for development of new synthetic approaches to these systems, as the existing routes often require time-consuming multistep preparation of rather complex starting materials, giving only low overall yields of the desired products.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Fused 1-Sila-, 1-Germa-, and 1-Selenacyclohepta-2,4,6-trienes

Shirani

Janosik

2008

Organometallics

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A concise route to 1-sila-, 1-germa-, and 1-selenacyclohepta-2,4,6-trienes containing two fused benzo[b]thiophene units is described. Metalation of the ethylene acetal of 3-bromobenzo[b]thiophene-2-carboxaldehyde and subsequent quenching with Me 2 SiCl 2 , Me 2 GeCl 2 , or (PhSO 2 ) 2 Se gave the corresponding bis(benzo[b]thiophen-3-yl)silane, -germane, or -selenide, respectively, which were subjected to deprotection, followed by McMurry coupling, eventually affording the target compounds in good overall yields. It was also concluded that application of this approach to synthesis of related benzo-fused metallacyclohepta-2,4,6-trienes is limited to electron-deficient targets, as attempts involving electronrich substrates failed or gave only low yields at the final McMurry coupling stage.

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The place of dibenzo[b,f]thiepin derivatives in medicinal chemistry: Structures and activities

Cited by 13 publications

References 195 publications

Valence isomerization of cyclohepta-1,3,5-triene and its heteroelement analogues

Valence isomerization of cyclohepta-1,3,5-triene and its heteroelement analogues

Seven‐Membered Heterocycles: Azepines, Benzo Derivatives and Related Systems

Synthesis of Fused 1-Sila-, 1-Germa-, and 1-Selenacyclohepta-2,4,6-trienes

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