Applications of the spiroannulation of tetralins with alkynes; towards new anti-estrogenic compounds

Boyle, F. Thomas; Hares, O.; Matusiak, Zbigniew S.; Li, Warren; Whiting, Donald A.

doi:10.1039/a702992f

Cited by 12 publications

(11 citation statements)

References 9 publications

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“…24 l-Iodo-2-naphthalenecarboxaIdehyde (12). Compound 12 was obtained as a light yellow solid in a 60% overall yield: mp 106-107 °C; *H NMR (CDCI3, 300 MHz) ô 7.57-7.60 (m, 2H), 7.70-7.73 (m, 2H), 7.78-7.81 (d,/= 8.7 Hz,1H),1H); 13 C NMR (CDCI3, 300 MHz) 5 124.96, 128.71, 128.83, 129.50, 129.94, 133.45, 134.03, 134.61, 137.10, 197.72; IR (CHC13) 1680 cm" 1 ; HRMS m/z 281.9545 (calcd for CnH7IO, 281.9542).…”

Section: Methodsmentioning

confidence: 99%

“…The reaction mixture was chromatographed using 5:1 hexane/EtOAc to afford 39 mg (45%) of the product as a colorless oil: NMR (CDC1 3 , 400 MHz) ô 7.05-7.06 (m, 1H), 7. 21-7.24 (m, 1H), 7.42-7.53 (m, 3H), 7.61-7.63 (d,7 = 8.4 Hz,1H),2H),7 = 7.6 Hz,1H); 13 C NMR (CDCI3,100 MHz) 5 124. 08,126.28,126.54,126.57,127.05,127.25,127.92,128.68,129.87,130.03,132.21,132.61,135.04,139.78;IR (CHCI3) 3062, 2925, 2853, 1584 cm 1 ;…”

Section: -(2-bromo-l-naphthyl)thiophene (11)mentioning

confidence: 99%

“…The reaction mixture was chromatographed using 10:1 hexane/EtOAc to afford 86 mg (55%) of the product as a colorless oil: ! H NMR (CDC1 3 ,400 MHz) ô 3.64 (s, 3H), 6.69-6.70 (d,7 = 2.4 Hz,1H),7 = 2.4,8.8 Hz,1H),2H),3H),2H),7 = 9.2 Hz,1H); 13 C NMR (CDC1 3 , 100 MHz) ô 55. 15, 105.47, 118.40, 122.22, 127.65, 127.81, 127.89, 128.51, 128.66, 129.54, 130.07, 135.20, 138.56, 139.89, 158.28;IR (CHCI3) 3058, 3001, 2959, 2937, 2838 02, 56.87, 81.10,106.18, 127.74,128.32,128.83,129.15,129.65,134.94,150.50,151.31,152.34,185.39; IR CH 2 C1 23369, 1667, 1613 cm" 1 ; HRMS m/z 363.9968 (calcd for CI 6 HI 3 I0 2 , 363.9960).…”

Section: -Bromo-7-methoxy-l-phenylnaphthaiene (32)mentioning

confidence: 99%

“…The reaction mixture was chromatographed using hexane to afford 96 mg (83%) of the product as a white solid: mp 116-117 °C; 'H NMR (CDCI3,300 MHz) ô 7.37-7.52 (m, 7H), 7.70-7.77 (m, 2H), 7.96-7.99 (d,7=8.4 Hz,1H),1H); 13 C NMR (CDC1 3 ,75 MHz) 5 96. 84, 121.99, 122.10, 122.78, 124.88, 127.46, 128.90, 128.99, 129.37, 135.61, 135.65, 135.85, 140.30, 141.18, 141.35, 143.11;IR (CHC1 3 ) 3056, 2918, 2360, 2849,1564 23, 23.13, 25.55, 27.76, 96.06, 121.22, 121.98, 122.81, 124.68, 127.28, 129.29, 135.25, 135.58, 135.89, 140.18, 140.51, 141.24, 143.33;IR (CHCI3) 3062, 2933, 2834, 2853, 1432 cm" 1 ; HRMS m/z 389.9946 (calcd for CisHisIS, 389.9939); Anal.…”

Section: -Iodo-4-phenyidibenzo[6]thiophene (44)mentioning

confidence: 99%

“…The combined organic layers was washed further with 25 mL of satd aq NaCl.The organic layer was dried over MgSQ* and filtered. The solvent was evaporated under reduced pressure and the product was isolated by chromatography on a silica gel column.The spectra for 4-phenylquinoline (78) 34 and 4-n-butylquinoline (The reaction mixture was chromatographed using 10:1 hexane/EtOAc to afford 62 mg of the product (88%) as a light yellow oil: ), 7.44-7.53 (m, 3H), 7.70-7.75 (m, 1H), 7.96-7.99(d, 7=8.4 Hz, 1H), Hz, 1H), 7 = 4.5 Hz, 1H);13 C NMR (CDC1 3 ,100 MHz) Ô 55.…”

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confidence: 99%

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Palladium and iodine approaches to 1,3-dienes, heterocycles and carbocycles

Zhang¹

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The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleed-through, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion.

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Section: Methodsmentioning

confidence: 99%

Section: -(2-bromo-l-naphthyl)thiophene (11)mentioning

confidence: 99%

Section: -Bromo-7-methoxy-l-phenylnaphthaiene (32)mentioning

confidence: 99%

Section: -Iodo-4-phenyidibenzo[6]thiophene (44)mentioning

confidence: 99%

mentioning

confidence: 99%

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Palladium and iodine approaches to 1,3-dienes, heterocycles and carbocycles

Zhang¹

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ChemInform Abstract: Applications of the Spiroannulation of Tetralins with Alkynes; Towards New Anti‐Estrogenic Compounds.

et al. 1998

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fused phenylcycloalkyl derivatives fused phenylcycloalkyl derivatives (rings with 3, 4, 7 or more members) Q 1040 -087Applications of the Spiroannulation of Tetralins with Alkynes; Towards New Anti-Estrogenic Compounds. -With a view to obtaining biologically interesting compounds the derivatives such as (VI) are synthesized. In a model system it is shown that a similar reaction to derivatives such as (VI) with ethyne or mono-or bistrimethylsilylethyne is not possible or gives very low yield with no selectivity. Therefore in a second approach the parent carbocycle (IX) missing the aryl substituent is developed. -(BOYLE, F. T.; HARES, O.; MATUSIAK, Z. S.; LI, W.; WHITING, D. A.; J.

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Synthesis of [2‐(Trimethylsilyl)ethynyl]pyrazoles Based on Bis(trimethylsilyl)acetylene and Arylacetyl Chlorides

et al. 2012

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A practical approach to the synthesis of [2‐(trimethylsilyl)ethynyl]pyrazoles was developed through condensation of hydrazines with enynones that are easily accessible frombis(trimethylsilyl)acetylene and arylacetyl chlorides. Optimized conditions for reactions with monoarylhydrazines permit the chemoselective formation of 5‐alkynylpyrazoles in high yields (48–94 %). When monoalkylhydrazines or the parent hydrazine is used, mixtures of 3‐ and 5‐alkynylpyrazoles are formed in 73–79 % yields. The method uses inexpensive starting materials and can be applied to a variety of substrates, which makes it convenient for the synthesis of alkynylpyrazoles.

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Applications of the spiroannulation of tetralins with alkynes; towards new anti-estrogenic compounds

Cited by 12 publications

References 9 publications

Palladium and iodine approaches to 1,3-dienes, heterocycles and carbocycles

Palladium and iodine approaches to 1,3-dienes, heterocycles and carbocycles

ChemInform Abstract: Applications of the Spiroannulation of Tetralins with Alkynes; Towards New Anti‐Estrogenic Compounds.

Synthesis of [2‐(Trimethylsilyl)ethynyl]pyrazoles Based on Bis(trimethylsilyl)acetylene and Arylacetyl Chlorides

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