Detail of "27988-97-2"

Reference

Synthesis of Fused Tetrazole Derivatives via a Tandem Cycloaddition and N-Allylation Reaction and Parallel Synthesis of Fused Tetrazole Amines

Synthesis of Fused Tetrazole Derivatives via a Tandem Cycloaddition and N-Allylation Reaction and Parallel Synthesis of Fused Tetrazole Amines. Ek, Fredrik; Manner, Sophie; Wistrand, Lars-Goeran; Frejd, Torbjoern ( Organic Chemistry 1, Department of Chemistry, Lund University, Lund S-221 00, Swed.). Journal of Organic Chemistry, 69(4), 1346-1352 (English) 2004 American Chemical Society. CODEN: JOCEAH. ISSN: 0022-3263. DOCUMENT TYPE: Journal CA Section: 28 (Heterocyclic Compounds (More Than One Hetero Atom)) A method for the synthesis of novel fused tricyclic tetrazoles from allylic bromides generated by the recently discovered DiazAll reaction has been developed. This new tandem reaction comprises a cycloaddn. between a nitrile and (TMS)N3 followed by an intramol. N-allylation. The variation of functionalities in the benzene moiety was well-tolerated, and only a moderate difference in yield and degree of purity was noticed. An exo-methylene group in these new compds. permitted further derivatization. Structural resemblance with substances which possess important pharmacol. properties (e.g., losartan and flumazenil) motivated the synthesis of a series of ketones and a small library of amines. 671795-65-6 which is the cas registry number of some chemical is mentioned. A comparison was made between the pharmacophore of (-)-epibatidine and a low energy conformation of N-methyl-5H-tetrazolo[5,1-a][2]benzazepin-6-amine. The reaction of 2-aminobenzonitrile derivs. with 3-bromo-2-(bromomethyl)-1-propene in the presence of tert-Bu nitrite gave 2-[2-(Bromomethyl)-2-propenyl]benzonitrile derivs. I (R = 5-Cl, 5-Br, 4-NO2, 5-NO2, 4-CF3, 4-Cl-5-Br). Treatment of I with (azido)trimethylsilane in the presence of dibutyltin oxide and sequential ozonization gave 5H-tetrazolo[5,1-a][2]benzazepin-6-ones II (same R). Further reductive amination of II gave tetrazolo[5,1-a][2]benzazepin-6-amines III (same R, R1 = H, PhCH2; R1R1N = morpholino, etc.). .

Tetrazoles

Tetrazoles. XXII. N-Hetaryltetrazoles. I. Tetrazolyltetrazolo[1,5-a]pyrimidines, intermediates in the formation of s-triazolo[4,3-c]tetrazolo[1,5-a]pyrimidines. Koennecke, A.; Lippmann, E. (Sekt. Chem., Karl Marx Univ., Leipzig, Ger.). Tetrahedron Lett., (25), 2187-8 (English) 1977. CODEN: TELEAY. DOCUMENT TYPE: Journal CA Section: 28 (Heterocyclic Compounds (More Than One Hetero Atom)) Reactions of 5-phenyltetrazole and tetrazole with 5-chloro-7-methyltetrazolo-[1,5]a-pyrimidine in the presence of equimolar NEt3 at room temp. gave 91 and 87% tetrazolyltetrazolopyrimidines I and II, resp. The triazolotetrazolopyrimidine III was formed .apprx. 30152-90-0 which is the cas registry number of some chemical is mentioned. quant. by thermolysis of I in PhCl (even with added dipolarophiles) and directly (85%) by reaction of the chlorotetrazolopyrimidine and 5-phenyltetrazole in boiling PhCl/NEt3. Treatment of I with F3CCO2H led to protonation of the tetrazolopyrimidine ring and then N extrusion to give 90% III on addn. of H2O. Thus I is an intermediate in the formation of III whereas II, which is stable in F3CCO2H, is not a precursor for compds. of type III. .