A new ring-opening reaction of 3-chloro-1,2-benzisothiazole

Carrington, D. E. L.; Clarke, K.; Scrowston, R. M.

doi:10.1016/s0040-4039(01)96630-4

Cited by 13 publications

(3 citation statements)

References 4 publications

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“…General Procedure for Aminobenzo[b Jthiophenes (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11). To a mechanically stirred, cold solution (ice bath) containing 30 mmol of the substituted o-nitrobenzonitrile in 100 ml of DMF was added dropwise a solution containing 36 mmol of sodium sulfide (nonahydrate) in 20 ml of water.…”

Section: Experimental Section10mentioning

confidence: 99%

“…General Procedure for Aminobenzo[b ]thiophenes 13-15. To a stirred, cold solution (ice bath) containing 30 mmol of the substituted o-nitrobenzonitrile and 3.1 g (36 mmol) of 3-mercaptopro-pionitrile9 in 60 ml of DMF was added dropwise a solution of 5 g of potassium hydroxide in 15 ml of water. The mixture was stirred in the cold for 15 min (30 min for preparation of 14), and the alkylating agent (3 ml of chloroacetonitrile for 13 and 15; 3.5 ml of chloroacetone for 14) was added dropwise. After it had been stirred in the cold for an additional 2 hr, the mixture was poured into ice water.…”

Section: Experimental Section10mentioning

confidence: 99%

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Synthesis of 2-cyano, 2-acyl, and 2-carboxamido derivatives of 3-aminobenzo[b]thiophene involving nitro displacement

Beck¹,

Yahner²

1974

J. Org. Chem.

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Section: Experimental Section10mentioning

confidence: 99%

Section: Experimental Section10mentioning

confidence: 99%

Synthesis of 2-cyano, 2-acyl, and 2-carboxamido derivatives of 3-aminobenzo[b]thiophene involving nitro displacement

Beck¹,

Yahner²

1974

J. Org. Chem.

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“…Small amounts of dicyclopropyl ketone (11) and of cyclopropyl cyclopropylmethyl ketone (12) were isolated in studies on 7 under both of the above reaction conditions. Since similar products had been obtained in related work,13 we studied the alkaline decomposition of 7 in water-glyme with and without added lithium nitrate.…”

mentioning

confidence: 99%

Alkali-induced reactions of N-nitrosooxazolidones and N-nitrosoacetylamino alcohols containing cyclopropyl groups

Newman¹,

Gromelski²

1972

J. Org. Chem.

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The reactions'of 5-cyclopropyl-5-phenyl-3-nitrosooxazolidone (6), 5,5-dicyclopropyl-3-nitrosooxazolidone (7), and 5-cyclopropyI-5-methyl-3-nitrosooxazolidone (8) under alkaline conditions are described. When methanolic solutions of 6 are treated with aqueous hydroxide, about 90% yields of cyclopropylphenylacetylene (9a) are obtained. On similar treatment, 7 yields about 52% dicyclopropylacetylene (9b) together with about 21% 2,2dicyclopropylvinyl methyl ether (10b), and 8 yields only 16% cyclopropylmethylacetylene (9c) together with about 64% a nearly 1:1 mixture of the Z and E forms of 2-cyclopropyl-l-propenyl methyl ether (10c). When a cyclohexene solution of 6 is added to a suspension of lithium ethoxide in cyclohexene, an 84% yield of 9a is obtained. On similar treatment, 7 yields 64% 9b and about 13% 7-(dicyclopropylmethylene)bicyclo[4.1.01heptane (5b), while 8 yields about 26% 9c and 44% 7-(2-cyclopropylpropylidene)bicyclo[4.1.0]heptane (5c). Mechanisms which involve unsaturated carbonium ions and unsaturated carbenes are advanced to explain the results. Treatment of a cyclohexene-pentane solution (containing a small amount of Aliquat, a long chain quaternary ammonium chloride) of 2-(A7-nitrosoacetylamino)-l,l-dicyclopropylethanol ( 17) with 50% sodium hydroxide afforded a 64%¡ yield of 5b. Similar treatments of l-(iV-nitrosoacetylamino)-2-cyclopropyl-2-propanol (18) yielded 52% 5c.The reactions of 5,5-disubstituted-3-nitrosooxazolidones (I) with bases in polar media have been studied.3®

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