Chemistry of bivalent carbon intermediates—IV

Gutsche, C. David; Bachman, Gerald L.; Coffey, R. S.

doi:10.1016/s0040-4020(01)92713-9

Cited by 61 publications

(14 citation statements)

References 50 publications

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“…Method A. 4-Methoxy-2-methylbenzoic Acid Hydrazide (21). A mixture of 4-methoxy-2-methylbenzoic acid (8.33 g, 0.05 mol) and SOCl2 (7.25 mL, 0.1 mol) was refluxed for 2 h. The reaction mixture was concentrated under vacuum; the residue was dissolved in C6H6 and evaporated under reduced pressure to give 9.3 g of the corresponding benzoyl chloride 6, which was then used without further purification.…”

Section: ~20mentioning

confidence: 99%

A new class of nonhormonal pregnancy-terminating agents. Synthesis and contragestational activity of 3,5-diaryl-s-triazoles

Omodei-Salè¹,

Consonni²,

Galliani³

1983

J. Med. Chem.

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A series of 3,5-diaryl-s-triazoles were synthesized and evaluated as postimplantation contragestational agents. The introduction of various substituents (e.g., an o-alkyl chain on one phenyl and a m-alkoxy group on the other) was found to increase the potency. Several compounds with very high pregnancy-terminating activity in both hamsters and rats were obtained. One of these, 3-(2-ethylphenyl)-5-(3-methoxyphenyl)-s-triazole, DL 111 (36), was selected for detailed evaluation in various animal species. A synthetic scheme for the preparation of these compounds and preliminary structure-activity relationships are presented.

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Section: ~20mentioning

confidence: 99%

A new class of nonhormonal pregnancy-terminating agents. Synthesis and contragestational activity of 3,5-diaryl-s-triazoles

Omodei-Salè¹,

Consonni²,

Galliani³

1983

J. Med. Chem.

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“…A mechanism involving the siinultaneous abstraction of two neighboring hydrogen atoins has been suggested in the carbene field (26).…”

Section: + C H~c G I I ~N H S O~c H~mentioning

confidence: 99%

The Reaction of Sulfonylimido Intermediates With Aromatic Compounds

Abramovitch¹,

Roy²,

Uma³

1965

Can. J. Chem.

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'Therlnolysis of rnethanesulfonyl azide in aromatic solvents gives tnethanesulfonarnide and the isomeric niethanesulfonanilides. The orientation of the latter and the relative reactivities of the aromatic substrate towards attack by the ~nethylsulfonylimido intermediate have been studied quantitatively. The high reactivity and also great selectivity of the attacking species are interpreted in terms of a rate-determining addition process to give a sulfonylaziridine derivative followed by a product-deterlllining ring opening and rearrangement t o the substituted anilides. Partial rate factors are discussed, as are possible mechanisms for the formation of the rnethanesuifonamide. The ~netl~anesulfonylimido intermediate must be abstracting two hydrogen atoms synchronously from the aromatic substrate.

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“…2-Methoxybenzophenone (96.9%); b.p. 126128 "C (0.9 mmHg); 6H(cc14) 3.06 (3 H, s, OMe) and 6.62-7.76 (9 H, m, ArH); m/z 212 ( M + , 3573, 195 (18) 13)and91 (100).…”

Section: Methodsmentioning

confidence: 99%