Further studies on the cyclisation of 3-hydroxy-2'-nitrodiphenyl ethers and related compounds

Bird, C. W.; Latif, Marwa Abdel

doi:10.1016/0040-4020(80)80079-2

Cited by 4 publications

(3 citation statements)

References 4 publications

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“…Calc. for C24H13N3S3 C,65.6;H,3.0;N,9.6; S, 21.9%); ~,,,,,,(CHCl,) 267, 375, 537sh, and 576 nm (log E 4.42, 4.37, 4.16, and 4.31); m/z (%) 439 (M', loo), 407(25), 375 (7), and 343 (3.5); (ii) 2,2'-diaminophenyl disulphide, m.p. 92-93 "C (lit.,'8 93 "C) (0.25 g, 40%); m/z (%) 248 ( M + , 28) and 124 (1 00).…”

Section: -O-nitrophenylthio-12-naphthoguinonementioning

confidence: 99%

“…C2,H19NOS requires C, 76.5; H, 5.6; N, 4.1; S, 9.3%; M, 345.1187); h,,,,(CHCl,) 310 and 645 nm (log E 4.15 and 3.58); v,,,. (KBr) 1 633 cm-'; &,(CDCl,) 7.97 (1 H,m, 9-H), m,ArH),7.10(1 H,s, 3-H), and 1.34 (9 H, s, Bu'); m/z (%) 345 (M', loo), 330 (lo), 315 (9), 302 (8), 287 (7), and 286 (7).…”

Section: (23)mentioning

confidence: 99%

“…The product was chromatographed on silica (CHC1,-MeOH; 99: 1) to give, besides o-nitrothiophenol and the disulphide, 2-hydroxy-1,4-naphthoquinone, Table 1. Fractional atomic co-ordinates ( x lo4) for compound (11) with estimated standard deviations in parentheses (e.s.d.s) X 0 626(5) 0 278( 5) 1061 (6) 2 163(6) 3 039(6) 2 640(6) 3 526(5) 3 388(6) 4 374(7) 4 266(9) 3 196(9) 2 218( 8) 2 309( 6) 1516( 6) 2 587( 6) 1561 (7) 3 337(8) 3 240(8) 4 073( 5) 1012(2) -3 660( 5) -4 876( 6) -3 444( 6) -2 349( 6) -1 626( 5) -0 702(4) -0 591( 6) -1 445(5) 0 465(7) 0.490( 8) -0 497( 9) -1 549( 8) -1 597 (6) -2 903(2) -2 741(5) -2 154 (7) -1 333 (9) -0 353(3) -3 274( 8) -1 664 (7) Y 7 399(5) 6 572(6) 6 758(6) 6 811(6) 7 668(7) 8 518(6) Table 4. Torsion angles (") for compound (11) (Atoms in italics are not included in the derivation of the mean planes.)…”

Section: -O-nitrophenylthio-12-naphthoguinonementioning

confidence: 99%

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Quinones. Part 11. The reaction of o-aminothiophenol with o-benzo- and o-naphtho-quinones: a new route to 1H-phenothiazin-1-ones

Mackenzie¹,

Surendrakumar²,

Thomson³

et al. 1986

J. Chem. Soc., Perkin Trans. 1

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H-Phenothiazin-1 -ones can be obtained by the condensation of o-aminothiophenol with 3,5-di-tbutyl-and 3-t-butyl-5-phenyl-o-benzoquinones. In the absence of large blocking groups the phenothiazinones are unstable. A methyl group at C -4 leads via the quinone-methide tautomer, to formation of a spiro-dimer the crystal structure of which was determined by X-ray analysis. By further reaction with o-aminothiophenol, 1 N-phenothiazin-1 -ones yield triphenodithiazines (benzothiazinop henot h iazi nes) .

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Section: -O-nitrophenylthio-12-naphthoguinonementioning

confidence: 99%