Science of Synthesis Guided Examples
Science of Synt hesis Guided Exam ples
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Science of Synthesis Guided Exam ples
Com piled by: Dr. Thom as Krim m er
Ta ble of Cont e nt s 1 Exact St ruct ure Search .......................................................................... 2 2 Houben-Weyl ....................................................................................... 5 3 React ion Search ................................................................................... 6 4 Out bound Linking ............................................................................... 10
Science of Synt hesis Guided Exam ples
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1 Exact St ruct ure Search
Draw 2- Phenyl- Pyrim idine ( depict ed above) using one of t he t hree support ed drawing t ools, t hen select " Exact St ruct ure" from t he " Search As" opt ions.
Click
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N ot e : Perform ing t his search in SciFinder ( CAS) will generat e 15,565 hit s 15% of which relat e t o t he synt hesis of 2- Phenyl- Pyrim idine. This am ount s t o approxim ately 2,300 links to original papers.
Ext ract ing t he inform at ion you need from t his list m ay be difficult : assum ing you have access to all the j ournals, how do you process all these hits to isolat e the useful inform ation? And how can you be sure that the m ethods you settle on will work?
Perform ing t he search in Crossfire ( Beilst ein) will give only 1 hit since Crossfire is a subst ance dat abase. Clicking on " Synt hesize t his" will lead t o a couple of hit set s, which m ainly link to patents or very old literature.
Perform ing t he above search in Science of Synt hesis will generat e a concise hit list of t ransform ations t hat have been proven to work reliably on a num ber of different subst rat es. To decide which m et hod t o use for any given t ransform at ion, Science of Synthesis is the ideal tool.
N ot e : You would not use Science of Synt hesis if you are searching for a specific com pound. The focus of Science of Synt hesis is specific funct ional group t ransform ations, rat her t han t he various product s t hat m ay result .
Nor would you use Science of Synt hesis for an exhaust ive overview over all possible synthetic routes for a given transform ation: Science of Synthesis only presents t he m ost useful and reliable m ethods selected by its expert authors.
Science of Synt hesis Guided Exam ples
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I n Science of Synt hesis t he hit list is displayed in t he right - hand fram e. Each hit shows t he subst ance class ( in t his case: " Pyrim idines" ) , t he t ype of t ransform at ion ( e.g. hit 2: " Therm olysis of 2- Alkyl- 1,2- dihydro- 1,3,5- t riazoles" ) and t he single step reaction( s) found in the hit docum ent.
Clicking on a react ion schem e will lead you direct ly t o t he full- t ext docum ent , as will clicking on t he link below t he schem es ( e.g. Science of Synthesis, (2003) 16, 420 connect s you t o Science of Synt hesis volum e 16, page 420) .
I n t he header, you can see t hat your exact st ruct ure search for 2- Phenyl- Pyrim idine results in 4 hits:
N ot e : You can br owse t hrough t he hit docum ent s by clicking t he green arrows left and right of the st atus field:
Science of Synt hesis is not m erely a database but a reference work for organic t ransform ations: all 4 hit s deliver reliable m ethods to synthesize 2- Phenyl- Py rim idine:
? Hit 1: By React ions of Malonaldehyde Diacet als
? Hit 2: By Therm olysis of 2- Alkyl- 1,2- dihydro- 1,3,5- t riazines
? Hit 3: By Dehydrogenat ion of Tet rahydropyrim idines
? Hit 4: React ion of ( Trialkylst annyl) pyrim idines wit h Acid Chlor ides and Aryl Halides
Science of Synt hesis Guided Exam ples
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Click on t he st ruct ure in t he t hird hit t o br ing up t he corr esponding docum ent :
The t ransform at ion cont aining your search st ruct ure is highlight ed in a yellow box and a generally applicable preparative m ethod is given t owards the end of the docum ent . This m et hod can be used in t he laborat ory im m ediat ely, wit hout having t o consult t he prim ary lit erat ure. You m ay copy and past e, or print , any part of t he docum ent as necessary.
N ot e : You m ay print t he docum ent you are current ly viewing by clicking on t he print icon in t he t op right - hand corner of t he screen. ( The docum ent will display in low resolution, but print in high resolution).
I n t he int eract ive t able of cont ent s in t he left - hand fram e t he t it le of t he docum ent
currently displayed is highlighted:
.
N ot e: The t able of cont ent s gives rapid access t o relat ed m et hods t hat m ight not be part of your hit list . These m et hods use sim ilar chem ist ry and m ay offer valuable alt ernat ives t o solve your synt hesis problem . To print out all relat ed m et hods, click on t he chapt er heading ( in t his case, " By Oxidat ion" ) and use t he print icon in t he top-right hand corner of the left -hand fram e.
Preparat ive m et hods given in Science of Synt hesis are " General Procedures" or " Typical Procedures" . You can be assured t hat t hey have been applied on a range of subst rat es, under a variet y of condit ions, in num erous laborat ories. Science of Synt hesis aim s t o present a com pilat ion of t he best m et hods for synt hesizing any given class of com pounds.
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2 Houben-W eyl
At the foot of each docum ent in Science of Synthesis, you will find links to the relevant prim ary lit erat ure, as well as, where applicable, links t o relat ed sect ions of t he electronic back file (Houben-Weyl):
Houben-Weyl is part icularly useful if you are looking for a robust m ethod, which does not so m uch require expensive, st ate-of- t he- art equipm ent or t he use of precious cat alyst s.
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