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huyuanfei

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专业: 无机合成和制备化学

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112：7429m Ring-opening reactions of mesoionic [1,2,4]tiriazolo[1,5-c]quinazolines. Preparation of 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles by a translocative rearrangement. Molina,Pedro;Arques, Antonio; Alias,Maria Asuncion; Llamas Saiz, Antonio Luis;Foces-Foces, Maria da la Concepcion (Fac. Cienc., Univ.Murcia,Murcia,Spain 30071).Liebigs Ann. Chem. 1989, (11),1055-9(Eng).1-Amino-5-aryl-2mercapto-1H-[1,2,4]triazolo [1,5-c]quinazolin-4-ium hydroxides (Ⅰ,R=Ph,substituted Ph) undergo ring opening by the action of HCl to give 4-amino-3-[2-(aroylamino)phenyl]-4,5-dihydro-5-thioxo-1H-1,2,4-triazoles Ⅱ.Reaction of Ⅱ whit P2S5 yields 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles Ⅲ.
The mol.structure of Ⅲ (R=4-MeC6H4) has been solved by x-ray diffraction methods.

112:7435K The “tert-amino effect”in heterocyclic chemistry:synthesis of 3,1-benzoxazines and 3,1-benzothiazines.Nijhuis,W.H.N.;Verboom,W.;Harkema,S.;
Reinhoudt,D.N.(Lab.Org.Chem.,Univ.Twente,7500AE Enschede,Neth.).
Recl. Trav.Chim.Pays-Bas 1989,1008(4),147-59(Eng).Two routes are described for the synthesis of trifluoro[(dialkylamino)pheny]ethanonesⅠ(R=CF3;R1=H,R2=Me,OMe;n=1,2;R1=H,Me,CHOMe,R2=H,n=1; R1= R2=H,n=2) via trifluoroacetylation of N,N-disubstituted anilines or via Barbier reaction of 2-FC6H4CHO.Ⅰwere thermally converted to a mixt.of cis-and trans-pyrrolo-or pyridobenzoxazines Ⅱ(X=O).The mol.structure of Ⅱ was proven by x-ray crystal anal.of cis-Ⅱ（R=CF3,R1=H,R2=Me,X=O,n=1）and by 1H NMR. Ⅰ(R= R1= R2=H;R=Me, R1= R2=H; R=CF3, R1= R2=H,Me,n=1)reacted with Lawesson′s reagent to yield exclusively tians-pyrrolobenzothiazines Ⅱ (X=S,n=1)in 33-77% yields ,whereas Ⅰ(R=H,CF3,Me; R1= Me,R2= H;n=1)gave mixts.of various products.

112:7444n Development of a new synthesis of 3-(1H-tetrazol-5-yl)-4(3H)-quinazolinone,sodium salt via an amidine intermediate.
Vinogradoff,Anna P.;Peet,Norton P.(Western Appl.Sci.Technol.Lad.,Dow Chem.Co.,Pittsburgh,CA 94565 USA). J.Heterocycl. Chem. 1989, 26(1),97-103 (Eng). A new synthesis of the recently reported title compd .Ⅰ（MDL-427）,an exptl. mediator release inhibitor,was developed from sequential reaction of 5-aminotetrazole and HCl(OEt)3 to give Et N-(1H-tetrazol-5-yl)formimidate (Ⅱ),reaction of Me anthranilate and imidate Ⅱ to give amidine Ⅲ,and treatment of Ⅲ with base to give Ⅰ. Investigation of each of these higher-yielding 1-pot process. A brief examn. of anthranilic acid and its salts and derives. in this process found them to have dissimilar reactivities. The formation of amidine Ⅲ as an isolable intermediate was unusual,as was its failure to cyclize under std. neutral or acidic Conditions. The ads. Requirement for base to effect cyclization of Ⅲ is unprecedented.

[ Last edited by huyuanfei on 2008-12-9 at 22:01 ]

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