Flow vacuum pyrolysis of tetrazoles with annelated dibenzocycloalkane skeletons

被引：16

作者：

Banciu, MD

Popescu, A

Simion, A

Draghici, C

Mangra, C

Mihaiescu, D

Pocol, M

机构：

[1] Polytechn Univ Bucharest, Organ Chem Lab, Bucharest 76206, Romania

[2] Romanian Acad, CD Nenitzescu Inst Organ Chem, Bucharest 71141, Romania

来源：

JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS | 1999年 / 48卷 / 02期

关键词：

tetrazoloazocines; flow-vacuum pyrolysis; nitrenes; carbodiimides;

D O I：

10.1016/S0165-2370(98)00135-1

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

Three new dibenzoannelated tetrazoloazocines 1-3 were synthesized from the corresponding ketones 6-8 and in situ generated triazidochlorosilane. The new compounds were characterized by IR,H-1-, C-13-NMR and MS data. The flow-vacuum pyrolyses of the tetrazoles 1-3, of a recently described tetrazoloazonine 4 and of 1,5-diphenyltetrazole (5) at 1.33 mbar and temperatures between 400-550 degrees C were studied by GC/MS. The main reaction product of 1 was 6H-quinindoline whereas the principal products of 2, 3 and 4 were the corresponding ring contracted N-cyanoderivatives 11, 12 and 15, respectively. Diphenyltetrazole 5 afforded diphenylcarbodiimide and 2-phenyl-benzoimidazole. The comparative reaction mechanisms for 1-5 are discussed. The N-cyano-derivatives 11, 12 and 15 structurally are strongly related to recent anti-amnesia drugs. (C) 1999 Elsevier Science B.V. All rights reserved.

引用

页码：129 / 146

页数：18

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[21] A STEREOCONTROLLED SYNTHESIS OF (+)-THIENAMYCIN [J].