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У Levkoev, I. I.; Sveshnikov, N. N. в 1944-1946 было 6 совместных статей, из них в трех были лишние авторы.
При этом именно порядок начиная со Свешникова, одна единственная
При этом именно порядок начиная со Свешникова, одна единственная
Исходя из "N-thioacetyl-m-anisidine (37.2%), m. 51.5-2° (from 25% EtOH). This (8.72 g.) in 145 cc. 4% NaOH was added at 3-5° to 36.5 g. K ferrocyanide in 165 cc. H2O" и "identical with the product of ferrocyanide oxidn. given above" я считаю это таки ссылка 8 из статьи в прошлой теме, которая стоит на "окисление тиоацетильных производных o-, m-, p-анизидинов  окислением по методу Якобсона".Derivative of benzothiazole. II. Action of potassium ferrocyanide on thioacetyl-m-anisidine
By Sveshnikov, N. N.; Levkoev, I. I.
From Zhurnal Obshchei Khimii (1946), 16, 1071-6. | Language: Russian, Database: CAPLUS
cf. Kiprianov and Khrapal, C.A. 38, 969.1. m-Anisidine (12.3 g.) suspended in 50 cc. H2O was treated with 12.2 g. Ac2O at 15-20° to give 91.5% N-acetyl-m-anisidine, m. 79-80°. This (3.3 g.) in 16 cc. boiling C6H6 was treated with 0.9 g. powd. P2S5 and boiled 20 min.; the C6H6 ext. of the gummy residue and the original soln. were combined and extd. with 4% NaOH; the ext. was neutralized with AcOH and treated with CO2 to ppt. N-thioacetyl-m-anisidine (37.2%), m. 51.5-2° (from 25% EtOH). This (8.72 g.) in 145 cc. 4% NaOH was added at 3-5° to 36.5 g. K ferrocyanide in 165 cc. H2O with stirring and allowed to stand overnight, to yield, after Et2O extn. and treatment with picric acid, 77.5% picrates of mixed 5-methoxy- (I) and 7-methoxy-2-methylbenzothiazole (II), m. 133-40°. Decompn. of the picrates with soda gave 6.61 g. of a crude base mixt. which, warmed with 2 cc. ligroin, cooled, and partially evapd., gave 37.8% (II), m. 56-7° (from ligroin); picrate m. 162-3° (from EtOH); methiodide m. 203-5° (from EtOH); ethiodide m. 181-3° (from EtOH); propiodide m. 191-3° (from EtOH). The mother liquor from the II was converted into the picrate, m. 141-3°, which after crystn. from EtOH m. 161-2° and gave, after treatment with soda, 7% I, m. 38.5-9° (from ligroin); picrate m. 162-3° (from EtOH); methiodide m. 228-9° (from EtOH); ethiodide m. 187-8° (from EtOH); Me p-toluenesulfonate m. 165-6° (from abs. EtOH). I was synthesized for identification purposes by an independent method as follows. 3-Nitro-4-bromoanisole (11.6 g.) in 20 cc. boiling EtOH was treated over 30 min. with a Na polysulfide soln. from 6 g. cryst. Na2S and 1.2 g. S, and the mixt. boiled 3 h.; the sepd. oil was boiled with 10 cc. EtOH, then treated with Et2O to induce crystn. of bis(4-methoxy-2-nitrophenyl) sulfide (38%), m. 161-3° (from C6H6) (a 2nd crystn. gave a m.p. of 166-7°). This (3.68 g.) and 6.87 g. Zn dust were mixed and slowly added to 30 cc. AcOH at 80-100°, heated at 100° 0.5 h., treated with 6.12 g. Ac2O, heated 3 h. at 114-17°, cooled to 70-80°, dild. with 50 cc. H2O, heated to boiling, and filtered rapidly; the filtrate was made alk. and the oily I was extd. with Et2O, which was then removed in vacuo after drying to give 83.7% of a product, m. 38.5-9° (from ligroin), identical with the product of ferrocyanide oxidn. given above.
Я нашел точное название статьи И.И. Левкоев, Н.Н. Свешников "Исследование в области цианиновых красителей. Сообщение №1. О красителях производных антратиазолов. ЖОХ Том №15, стр. 215-224, 1945 год.
В Sci-finder оно имеет другого автора:
А что там должно быть? Потому как исходя из ссылки 8 в статье из прошлой темы там должно присутствовать окисление по якобсону, и оно фигурирует в абстракте упомянутой выше статьи Свешникова 1946 года.Cyanine dyes. I. Dye derivatives of anthrathiazoles
By Levkoev, I. I.; Durmashkina, V. V.
From Zhurnal Obshchei Khimii (1945), 15, 215-24. | Language: English, Database: CAPLUS
2-Methylanthra-[4,5,1',2']- and 2-methylanthra-[4,5,2',1']-thiazoles and their quaternary salts were synthesized, and from them cyanine dyes were prepd. and examd. as to optical and photographic value. The absorption max. of 4,5,4',5'- and 6,7,6',7'-dinaphthothiacarbocyanines is 61.5-3.5 mμ farther to the red than that of unsubstituted thiacarbocyanine; the shift is 1-2 mμ greater for the first deriv. than for the second. The dinaphtho derivs. are less effective as sensitizers than are the corresponding dibenzo derivs., probably because of higher mol. wt. and their easier coagulation in aq. soln. α-Aminoanthracene (11.6 g.) in 60 cc. benzene was treated with 7.34 g. Ac2O and refluxed for 15 min.; on cooling there was obtained 91% α-acetylaminoanthracene (I), m. 211-12° (from EtOH). Similarly, 83% β-acetylaminoanthracene (II), m. 237-8°, was obtained from β-aminoanthracene and Ac2O in AmOAc. I (14.1 g.) was ground with 6 g. P2S5 and carefully fused at 160° for 1-1.5 min. with stirring, the ground melt was boiled with 200 cc. EtOH, and the filtrate dild. with 800 cc. 5% NaOH, filtered, the filtrate neutralized with dil. AcOH, and the product pptd. by blowing with CO2; α-thioacetylaminoanthracene (40%) so obtained, m. 169-70°; somewhat better yield was obtained by condensation in boiling xylene; crystn. from EtOH gave the pure product, m. 177-8° (III). Treatment of II as above (fusion temp. 200-10°) gave 40% β-thioacetylaminoanthracene (IV), m. 211-12° (from EtOH). III (10.04 g.) in 100 cc. hot EtOH was treated with 128 cc. 5% NaOH, filtered, and cooled; the filtrate was added dropwise at 5° to 27.7 g. K3Fe(CN)6 in 150 cc. water; the mixt. was allowed to stand overnight, and filtered, and the solid dried; crystn. from 450 cc. EtOH with charcoal gave 70% 2-methylanthra-[4,5-1',2']-thiazole, m. 161-2° (V), further crystn. increased the m.p. 2°. V heated with excess Et p-toluenesulfonate to 160-70° for 6 hrs. gave 62% of the quaternary salt (VI), m. 226-7° (decompn.) after crystn. from EtOH. Treatment of its aq.-EtOH soln. with KI gave the ethiodide (VII), m. 223-4° (decompn.). IV by an analogous series of reactions gave 80% 2-methylanthra-[4,5,2',1']thiazole, m. 132-3° (from EtOH), (VIII); this was converted as above into the Et p-toluenesulfonate, m. 224-5° (decompn.), and ethiodide, m. 245-6° (decompn.). The dinaphthothiacarbocyanines were prepd. from ethyl p-toluenesulfonates of the anthrathiazoles and the corresponding esters of orthoformic and orthoacetic acids in pyridine at 135°; the dyes were purified by crystn. from EtOH, MeOH or CHCl3. The following derivs. were prepd. from VI and VIII: 3,3'-diethyl-4,5,4',5'-dinaphtho(β,β')thiacarbocyanine p-toluenesulfonate (86%), m. 261-2° (from CHCl3), deep green with golden sheen; 3,3'-diethyl-9-methyl-4,5,4',5'-dinaphtho(β,β') thiacarbocyanine p-toluenesulfonate (11.5%), m. 225° (from MeOH), deep green with coppery sheen; 3,3'-diethyl-6,7,6',7'-dinaphtho (β,β') thiacarbocyanine p-toluenesulfonate (83%), m. 305-6° (from EtOH), brown; 3,3'-diethyl-9-methyl-6,7,6',7'-dinaphtho (β,β') thiacarbocyanine p-toluenesulfonate (45%), m. 253-4° (from EtOH), brown with bronze luster. By pptn. with NaCl and NaI from aq. MeOH the corresponding halides were prepd.: 3,3'-diethyl-4,5,4',5'-dinaphtho(β,β')thiacarbocyanine chloride, deep green, m. 210-12° (decompn.) from MeOH; 3,3'-diethyl-4,5,4',5'-dinaphtho(β,β')thiacarbocyanine iodide, deep blue, m. 243-5° (decompn.) from MeOH; 3,3'-diethyl-6,7,6',7'-dinaphtho(β,β')thiacarbocyanine chloride, brown, m. 238-40° (decompn.) from EtOH; 3,3'-diethyl-9-methyl-4,5,4',5'-dinaphtho (β, β') thiacarbocyanine chloride, deep green, m. 194-5° (decompn.) from CHCl3; 3,3'-diethyl-9-methyl-6,7,6',7'-dinaphtho(β,β')thiacarbocyanine chloride, deep green with gold luster, decomps. 230° (from CHCl3). VI (0.45 g.) and 0.11 g. malonaldehyde dianil in 6 cc. pyridine were allowed to stand for 24 hrs.; 0.1 g. piperidine was added and after 48 hrs. the pptd. 3,3'-diethyl-4,5,4',5'-dinaphtho(β,β')thiadicarbocyanine p-toluenesulfonate was filtered off and washed with EtOH and Et2O; yield-38%; bronze needles (from CHCl3) m. 213-14° (decompn.); it was obtained in lower yields by analogous condensation in Ac2O with NaOAc or with ethoxyacrolein diethylacetal in pyridine; by analogous means there was obtained 52% 3,3'-diethyl-6,7,6',7'-dinaphtho(β,β')thiadicarbocyanine p-toluenesulfonate, m. 248-50° (decompn.) from MeOH, as shiny bronze needles. By the use of dianil of glutaconaldehyde there was obtained 3,3'-diethyl-4,5,4',5'-dinaphtho (β,β') thiatricarbocyanine p-toluenesulfonate, m. 202-4° (decompn., from MeOH), (66%), as shiny bronze needles; 3,3'-diethyl-6,7,6',7'-dinaphtho (β, β') thiatricarbocyanine p-toluenesulfonate, m. 196-9° (decompn.) from MeOH (80%), as copper-red plates. VI (0.45 g.) in 20 cc. EtOH was heated with 0.96 g. quinoline ethiodide, 0.05 g. Na in 2 cc. abs. EtOH was added, the mixt. was refluxed for 0.5 hr., and cooled; there was obtained 71% 3,1'-diethyl-4,5-naphtho(β,β')thia-4'-isocyanine iodide, green-brown needles, m. 250-1° (decompn.) from MeOH; analogously there was obtained 75% 3,1'-diethyl-6,7-naphtho(β,β') thia-4'-isocyanine iodide, red needles, m. 307-8° (decompn.) from MeOH. Condensation of VI with p-Me2NC6H4CHO in EtOH in the presence of piperidine at reflux gave, on cooling and addn. of Et2O, a tarry ppt. which was dissolved in EtOH and treated with aq. KI to yield 2-p-dimethylaminostyrylanthra-[4,5,1',2']-thiazole ethiodide, deep violet prisms, m. 206-7° (decompn.) from EtOH; its abs. max. in MeOH was 535.5 mμ.
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