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p. 777-790
Received: 13 July 2002; in revised form: 27 November 2002 / Accepted: 27 November 2002 / Published: 30 November 2002
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| Download PDF Full-text (281 KB) Abstract: The synthesis of 6-(2,5-dimethoxy-4-(2-aminopropyl)phenyl)hexylthiol, an agonist with a very high affinity for the 5HT2A serotonin receptor subtype is reported. This agonist was designed to be attached to highly fluorescent cadmium selenide/zinc sulfide core/shells via a thiol at the end of a linker arm. This conjugate has applications in biological assays and biological imaging.
p. 791-800
Received: 25 February 2002; in revised form: 11 November 2002 / Accepted: 14 November 2002 / Published: 30 November 2002
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| Download PDF Full-text (111 KB) Abstract: The title compounds were synthesized from C-aryl-N-methylglycines by Naroylation followed by a cyclodehydration to form the corresponding 1,3-oxazolium-5-olates. These were not isolated but converted to the title compounds by an in situ 1,3-dipolar cycloaddition/cycloreversion sequence using carbon disulphide. We have studied the cyclodehydration step using acetic anhydride, trifluoroacetic anhydride and 1,3-dicyclohexylcarbodiimide (DCC) at temperatures not exceding 60oC. Trifluroacetic anhydride proved to be the best reagent, giving a better yield and more easily purified products, although yields were also acceptable with the other two reagents.
p. 801-805
Received: 23 June 2001; in revised form: 13 November 2002 / Accepted: 13 November 2002 / Published: 30 November 2002
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| Download PDF Full-text (34 KB) Abstract: The 5,6,9,10-tetrahydro-7,8-benzocyclooctenedione 4 has been synthesized through fragmentation of a bicyclo[4.2.0]octane system using an acyloin reaction on the trans -2,3-dicarboethoxy-1,2,3,4-tetrahydronaphthalene 1 in the presence of trimethylchlorosilane (TMCS). The two intermediates of this reaction, bis(trimethylsiloxy) derivatives 2 and 3, have been isolated and characterized.
p. 806-809
Received: 15 October 2002; in revised form: 18 October 2002 / Accepted: 18 October 2002 / Published: 30 November 2002
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| Download PDF Full-text (68 KB) Abstract: Easy and effective preparations of nearly pure (diacetoxyiodo)arenes, ArI(OAc)2 , from iodoarenes, ArI, are reported. In most cases the crude colorless products thus obtained need not be further purified, i.e., by recrystallization. As an example, the PhI(OAc)2 thus prepared was 99% pure (by iodometry).
p. 810-812
Received: 15 October 2002; in revised form: 21 October 2002 / Accepted: 21 October 2002 / Published: 30 November 2002
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| Download PDF Full-text (17 KB) Abstract: Easy and effective preparations of the nearly pure [bis (trifluoroacetoxy)-iodo]arenes, ArI(OCOCF)3 , from some iodoarenes, ArI, are reported, using an anhydrous sodium percarbonate/(CF3 CO)2 O/CH2 Cl2 system. The colorless, freshly prepared ArI(OCOCF3 )2 thus obtained were 98-99% pure (by iodometry).
p. 813-816
Received: 22 October 2002; in revised form: 2 December 2002 / Accepted: 2 December 2002 / Published: 2 December 2002
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| Download PDF Full-text (34 KB) Abstract: Nα-Urocanylhistamine and two related compounds were synthesized by using PyBOP coupling protocols. These compounds represent naturally occurring histamine derivatives.
p. 817-832
Received: 1 September 2002; in revised form: 15 November 2002 / Accepted: 22 November 2002 / Published: 30 November 2002
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| Download PDF Full-text (175 KB) Abstract: The accumulation of isoflavonoid phytoalexins was studied in several Colombian bean cultivars resistant and susceptible to Colletotrichum lindemuthianum fungus, the causal agent of anthrachnose disease. A time-course accumulation analysis on seedlings treated with CuCl2 showed that phaseollin production was higher in resistant cultivars than in susceptible ones. Also, a defensive role of phytoalexins was demostrated when extracts containing this pterocarpan exhibited antifungal activity against C. lindemuthianum . In addition, the elicitor activity of some aminosugars was also established.
p. 833-839
Received: 20 May 2002; in revised form: 5 November 2002 / Accepted: 27 November 2002 / Published: 30 November 2002
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| Download PDF Full-text (83 KB) Abstract: Correlations of AM1 and PM3 theoretical data, 13 C-NMR substituent chemical shifts (13 C-SCS) and IR carbonyl group wave numbers [ν(C3 ═O)] were studied using dual substituent parameter (DSP) models for 5-substituted indole-2,3-diones. For the C7 atom a reverse substituent effect attributed to extended π-polarization was observed. On the other hand, the DSP approaches for the C3 atom showed normal substituent effects with some contribution of reverse effect supported strongly by 13 C-SCS correlations. In the ν(C3 ═O) and p(C3 ═O) DSP correlations the field effect contribution predominates over the resonance effect, which justifies the using of earlier suggested vibrational coupling (V-C) model for 5- and 6-substituted indole-2,3-diones.
p. 840-847
Received: 23 March 2002; in revised form: 5 November 2002 / Accepted: 7 November 2002 / Published: 30 November 2002
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| Download PDF Full-text (80 KB) Abstract: The reaction of alkyl-substituted benzenes with o-chloranil at an elevated temperature was found to give 4,5,6,7-tetrachloro-1,3-benzodioxoles via benzylic oxidation and subsequent acetal formation, albeit in poor yields.
p. 848-853
Received: 1 October 2002 / Accepted: 18 November 2002 / Published: 1 December 2002
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| Download PDF Full-text (34 KB) Abstract: By using broken lines to represent coordination interactions in organometallic and other coordinated compounds, we can draw structures satisfying the valencies of the atoms present. These broken lines should be used to replace many false single covalent bonds now used to depict organometallic and coordinated compounds. Chemical drawing software should not recognize such broken lines as single covalent bonds and they should be ignored. An example of confusing and erroneous structural representation of organometallics and coordination compounds is discussed.
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