List of used abbreviations - RosDok - Universität Rostock

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All products developed in this thesis allow for the efficient synthesis of highly functionalized organic sulfur compounds which are not readily available by other methods. 12
1. Synthesis of functionalized 2-(arylthio)benzoates by formal [3+3] cyclizations of 3-arylthio-1-silyloxy-1,3-butadienes with 3-silyloxy-2- en-1-ones and 1,1-diacylcyclopropanes 1.1 Introduction Functionalized diaryl sulfides are pharmacologically important molecules which occur in various natural products. For example, they are present in dibenzothiophenes, 9 varacins (lissoclinotoxins), 10 lissoclibadins, 11 cyclic sulfides, 12 and various other natural products isolated from Streptomyces griseus. 13 Diaryl sulfides are synthetically available by reaction of arenes with sulphur 14 and sulphur dichloride, 15 by condensation of organometallic reagents with chlorophenyl-sulfide 16 and by basemediated reaction of chloroarenes with thiophenols. 17 These reactions often suffer from their low regioselectivity and from the formation of polysulfides, due to the harsh reaction conditions. An alternative approach to diaryl sulfides is based on the use of sulfur-containing building blocks in cyclization reactions. Hilt and coworkers reported a convenient approach to diaryl sulfides by cobalt(I)-catalyzed [4+2] cycloaddition of alkynyl sulfides with 1,3-butadienes. 18 Recently, Langer et al. studied 19 the synthesis of 3- and 5-(arylthio)salicylates by TiCl4-mediated formal [3+3] cyclizations 20 of 1,3bis(silyloxy)-1,3-butadienes 21 with 3-silyloxy-2-en-1-ones. 22 Chan et al. reported the synthesis of methyl 4,6-dimethyl-2-(phenylthio)benzoate by TiCl4-mediated [3+3] cyclization of 4-trimetyhlsilyloxy-3-penten-2-one with 1-methoxy-3-phenylthio-1trimethylsilyloxy-1,3-butadiene. 23 I recently prepared 2-(arylthio)benzoates by catalytic cyclizations of 3-arylthio-1-trimethylsilyloxy-1,3-butadienes with 1,1,3,3tetramethoxypropane. 24 In addition, the synthesis of 6-alkyl- and 6-aryl-2- (arylthio)benzoates by cyclization of 3-arylthio-1-trimethylsilyloxy-1,3-butadienes with 13
Page 1 and 2: Synthesis of functionalized 2-(aryl
Page 3 and 4: The ink of the scholar is more holy
Page 5 and 6: Affectionately Dedicated to “All
Page 7 and 8: Table of Contents 03 List of used a
Page 9 and 10: RCM Ring Closing Metathesis TBAI Te
Page 11 and 12: humans: 1) the thiomethyl of methio
Page 13 and 14: Chart 3. Structure of sumatriptan S
Page 15: disulfide (DADS) and diallyl sulfid
Page 19 and 20: 3-Arylthio-1-trimethylsilyloxy-1,3-
Page 21 and 22: under kinetic reaction control, by
Page 23 and 24: l a u 4-FC6H4 H Me H 40 m a v 4-FC6
Page 25 and 26: Table 2. Synthesis of thioxanthones
Page 27 and 28: 3a O OSiMe 3 O OMe + Me Me Cl 3TiO
Page 29 and 30: Table 3. Synthesis of 8a-x 3 7 8 Ar
Page 31 and 32: Cl + SPh OSiMe 3 3a 9 O OMe O O H i
Page 33 and 34: solution. The use of an excess (1.5
Page 35 and 36: Table 4. Synthesis of 12a-r 3 11 12
Page 37 and 38: 2.3 Conclusion In conclusion, I hav
Page 39 and 40: aromatization). An unseparable 1:2
Page 41 and 42: Table 5. Synthesis of arenes 14a-l
Page 43 and 44: 3.3 Conclusion In conclusion, I hav
Page 45 and 46: Mass Spectroscopy: AMD MS40, AMD 40
Page 47 and 48: 131.0 (ArCH), 132.7, 134.0, 135.9,
Page 49 and 50: (EI, 70 eV): m/z (%): 380 (100), 21
Page 51 and 52: (m), 1490 (m), 1434 (m), 1383 (w),
Page 53 and 54: 15.4, 16.9, 18.9 (CH3), 28.3 (CH2),
Page 55 and 56: (C). IR (neat): ν̃ = 2945 (w), 29
Page 57 and 58: 948 (w) 853 (m), 803 (m), 751 (m),
Page 59 and 60: 135.4, 139.2, 143.8, 146.5, 182.2 (
Page 61 and 62: Me S O Me Ph Br Methyl 4-methyl-5-(
Page 63 and 64: 35 Cl, 37 Cl, 61), 430 (M + , 35 Cl
Page 65 and 66: ArH). 13 C NMR (62 MHz, CDCl3): δ
Page 67 and 68:
Me S O Me Me Methyl 4,6-dimethyl-5-
Page 69 and 70:
S Methyl 4-methyl-5-(2-bromoethyl)-
Page 71 and 72:
(CH2CH3), 33.3 (CH2), 40.1 (CH2), 5
Page 73 and 74:
Me 3,4-Dimethyl-2-phenylsulfanyl-be
Page 75 and 76:
Me 3,4-Dimethyl-2-(p-tolylsulfanyl)
Page 77 and 78:
OCH3), 7.08-7.17 (m, 7H, Ar); 13 C
Page 79 and 80:
(w), 750 (s), 732 (s), 688 (s), 650
Page 81 and 82:
35 Cl 35 Cl, 100), 359 (26), 357 (3
Page 83 and 84:
2924 (w), 2853 (w), 1728 (s), 1712
Page 85 and 86:
Me 3-Hydroxy-5-(4-methylphenylsulfa
Page 87 and 88:
Et 3-Hydroxy-5-(4-ethylphenylsulfan
Page 89 and 90:
(13), 264 (13), 262 (36) ,260 (12),
Page 91 and 92:
MS (EI, 70 eV): m/z (%) = 337 (16),
Page 93 and 94:
OH O 5'-Hydroxy-[1,1';3',1'']terphe
Page 95 and 96:
Refrences 1. Handbook of Chemistry
Page 97 and 98:
20. For a review of [3+3] cyclizati
Page 99 and 100:
Nationality Pakistan Place of Birth
Page 101 and 102:
Publications 1. Inam Iqbal, Muhamma
Page 103 and 104:
Tetrahedron 2007, 63, 12562-12575.
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List of used abbreviations - RosDok - Universität Rostock

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