A Derivative of a New Sulfur Heterocycle<sup>1</sup>

Scott, George P.

doi:10.1021/ja01120a531

Cited by 37 publications

(9 citation statements)

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“…It has also been reported that the 3-alkyl derivatives of the 3-benzostibepine are thermally labile and can be isolated only at low temperature, 14) and the C-unsubstituted arsepine (2a) 10) and thiepine (2e) 15,16) have also been known to be too thermally unstable to be isolated, although the 3-benzothiepines having alkoxycarbonyl groups in the 2-and/or 4-positions are stable and can be isolated at room temperature. [15][16][17][18][19] While it was considered in heteroepine chemistry that most of heteroepines were relatively unstable and difficult to isolate, we were interested in the synthesis of 3-benzoheteroepines under mild reaction conditions. We report here on a versatile synthetic route to the C-unsubstituted group 15 and 16 3-benzoheteroepines (2a-g) and 2,4-bis(trimethylsilyl) substituted heteroepines (17c, d, g), all of which can be isolated at room temperature except for 3-benzobismepine (2d), and on the thermal stabilities of these novel heterocyclic systems.…”

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confidence: 99%

A Versatile Route to 3-Benzoheteroepines Containing Group 15 and 16 Heavier Elements Involving Several Novel Ring Systems, and Their Thermal Stabilities

Yasuike

Kiharada

Tsuchiya

et al. 2003

CHEMICAL & PHARMACEUTICAL BULLETIN

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The C-unsubstituted 3-benzoheteroepines (2a-g) containing group 15 (P, As, Sb, and Bi) and group 16 (S, Se, and Te) heavier elements were prepared by the reaction of the corresponding metal reagents with (Z,Z)-obis(b b-lithiovinyl)benzene (5) which was derived in two steps from a common o-phthalaldehyde (3). The heteroepines (2) thus obtained were thermally labile towards heteroatom extrusion, and their half-lives on heating estimated from 1 H-NMR spectral analysis showed that the 3-benzoheteroepines (2) were far less stable than the corresponding 1-benzoheteroepines (1). The 2,4-bis(trimethylsilyl)-3-benzoheteroepines (17) containing Sb, Bi, and Te were also prepared from o-diiodobenzene (9) in 6 steps and were found to be more stable than the corresponding C-unsubstituted heteroepines (2).

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confidence: 99%

A Versatile Route to 3-Benzoheteroepines Containing Group 15 and 16 Heavier Elements Involving Several Novel Ring Systems, and Their Thermal Stabilities

Yasuike

Kiharada

Tsuchiya

et al. 2003

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Whilst process i) would originate the mono-episulfide-sulfide 23, which could suffer sulfur extrusion to the monoepisulfide 24, and subsequent electrocyclisation to mono-episulfide 25 before generating the alkaloid, process ii) would lead to 22 and thence to arcyriaflavin-A. Ready loss of sulfur from bis-episulfides or episulfide, leading to fully aromatic substances, has precedent in the literature [26,27].…”

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confidence: 99%

Recent developments in the synthesis of biologically active indole alkaloids

Labo

Prabhakar

2002

Journal of Heterocyclic Chem

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“…Methylation of (I) with dimethyl sulfate and potassium tert-butoxide in tetrahydrofuran at O' C, followed by chromatography of a benzene solution on silica Table. Comparison of (3), (4), and (5) with 3,S-diacetoxy-4-phenyl-lbenzothiepin ( 6 ) [ 5 ] . gel and rubbing with a little methanol, led to 5-methoxy-4phenyl-I-benzothiepin (5)[''] (see Table).…”

Section: Synthesis Of Stable 1-benzothiepins"lmentioning

confidence: 99%