Intramolecular cyclizations of diphenyl ether, benzophenone, and related 2-sulfonylnitrenes

Abramovitch, R. A.; Azogu, C.I.; MCMASTER, I. T.; Vanderpool, Danny P.

doi:10.1021/jo00400a042

Cited by 34 publications

(12 citation statements)

References 13 publications

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“…other relevant respects, the two series of 1.2-thiazepines show the expected similarity in spectral characteristics. Thus we feel that the structures of both our N-methyl derivativc 6 and its precursor 3c are secure.…”

Section: Resultsmentioning

confidence: 75%

Photochemical rearrangements of 2-azido-4-thiochromanone 1-oxide and 1,1-dioxide: formation of 2H-benzo[f]-1,2-thiazepine derivatives

Still¹,

LEONG²

1980

Can. J. Chem.

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Photolysis of 2-azido-4-thiochromanone 1,1-dioxide in benzene or dichloromethane leads to the formation of 2H-benzo[f]-1,2-thiazepin-5-one 1,1-dioxide, in very good yield. In contrast, the photolysis of the analogous sulfoxide was much more complex and no ring-expansion product could be isolated, although a small amount of a compound believed to be 2-aminothiochromone 1-oxide was formed. Several attempts to prepare the α-azidosulfide analogue, to compare its photochemical behavior, were unsuccessful and a rationale is proposed for the apparent instability of this member of the series.

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Section: Resultsmentioning

confidence: 75%

Photochemical rearrangements of 2-azido-4-thiochromanone 1-oxide and 1,1-dioxide: formation of 2H-benzo[f]-1,2-thiazepine derivatives

Still¹,

LEONG²

1980

Can. J. Chem.

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“…M.p. for (I): 388±389 K [literature value 386±388 K (Abramovitch et al, 1978)]; m.p. for (II): 354±357 K.…”

Section: Methodsunclassified

Monoclinic pseudosymmetry in 2-phenoxybenzenesulfonamide, a triclinic structure havingZ′ = 4, and spontaneous resolution in monoclinicN-methyl-2-phenoxybenzenesulfonamide

et al. 2004

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2-Phenoxybenzenesulfonamide, C(12)H(11)NO(3)S, (I), crystallizes in space group P-1 with Z' = 4, but the structure closely mimics the monoclinic space group P2(1)/b with Z' = 2. The molecules of (I) are linked by a combination of N-H...O and C-H...O hydrogen bonds into two independent chains of centrosymmetric edge-fused R(2)(2)(18) and R(6)(6)(34) rings. N-Methyl-2-phenoxybenzenesulfonamide, C(13)H(13)NO(3)S, (II), crystallizes in space group P2(1) with Z' = 1, and is an example of spontaneous resolution. The molecules are linked by N-H...O and C-H...O hydrogen bonds into chains of spiro-fused R(2)(2)(12) rings, and these chains are linked into sheets by a single C-H...pi(arene) hydrogen bond.

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“…These methods include oxidation of dibenzothiophene and multistep procedures, as well as require halogenated and metalated compounds. 4 Undoubtedly, the seminal intramolecular oxidative coupling via effective directing strategy for single C–H bond activation from simple precursors requires minimum prefunctionalization for expedite access to fused biaryl sulfones. However, current chemistry has not been successful to reach this goal; mainly due to weak coordinating properties of sulfone group.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Intramolecular Oxidative Arylations for the Synthesis of Fused Biaryl Sulfones

Laha

Sharma

2018

ACS Omega

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This study unveils palladium-catalyzed intramolecular oxidative cyclizations in biaryl and heterobiaryl sulfones providing direct access to fused biaryl sulfones (dibenzothiophene-5,5-dioxides). Variously substituted dibenzothiophene-5,5-dioxides could be readily prepared in good to excellent yields under optimized conditions. In addition, bromination afforded dibromo derivative of dibenzothiophene-5,5-dioxides, providing platform for late-stage diversification. The translational applications of this current protocol have successfully been demonstrated in the synthesis of 2,8-diamino derivative of dibenzothiophene-5,5-dioxides, a α 7 -nicotinic acetylcholine receptor agonist analogue, and novel single fluorene-tethered dibenzothiophene-5,5-dioxide, an organic emitter.

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Intramolecular cyclizations of diphenyl ether, benzophenone, and related 2-sulfonylnitrenes

Cited by 34 publications

References 13 publications

Photochemical rearrangements of 2-azido-4-thiochromanone 1-oxide and 1,1-dioxide: formation of 2H-benzo[f]-1,2-thiazepine derivatives

Photochemical rearrangements of 2-azido-4-thiochromanone 1-oxide and 1,1-dioxide: formation of 2H-benzo[f]-1,2-thiazepine derivatives

Monoclinic pseudosymmetry in 2-phenoxybenzenesulfonamide, a triclinic structure havingZ′ = 4, and spontaneous resolution in monoclinicN-methyl-2-phenoxybenzenesulfonamide

Palladium-Catalyzed Intramolecular Oxidative Arylations for the Synthesis of Fused Biaryl Sulfones

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