Organic Chemistry Commons^™

Synthesis Of Dihydroisoquinolines And Tetrahydroisoquinolines, John J. Schlager

Chemistry & Biochemistry Theses & Dissertations

Dihydroisoquinolines and tetrahydroisoquinolines are compounds which possess a variety of pharmacological activities. New easier methods of synthetic manipulations of these structures is of constant interest in the pharmaceutical industry.

This paper describes a new three step method of preparing 1-alkyl- and 1-aryl-tetrahydroisoquinolines from a tetrahydroisoquinoline. The synthesis involves the N-chlorination of tetrahydroisoquinoline followed by dehydrohalogenation with potassium superoxide. The reaction products are the dihydroisoquinolines. Overall yields range from 85-96%. The unsubstituted, 1-methyl-, and 1-phenyl-J,4-dihydroisoquinolines have been formed. Organometallation of the unsubstituted dihydroisoquinoline provides the 1-substituted tetrahydroisoquinoline. The 1-benzyl-, 1-n-butyl-, 1-ethyl-, 1-methyl-, and 1-phenyl-1,2,J,4-tetrahydroisoquinolines were prepared. The use of Grignard and …

A Technique For The Isolation And Identification Of Aliphatic Amines In Water, Peter Alan Drew

Chemistry & Biochemistry Theses & Dissertations

Small, aliphatic amines added to a basic, aqueous solution (16.2 L) at a concentration of 100 parts per billion were isolated by sorption on a small column of macroreticular resin. The amines were eluted with diethyl ether; the eluate concentrated, and the compounds separated and identified by gas chromatography. The efficiency of the recovery of a-nines ranged from 5 to 28%.

A protocol for derivatizing pyrrolidine and n-pentylamine in ether with fluorinated acylating agents was developed. The method was found to be adequate for the detection of approximately 13 micrograms of &-nines in concentrated ether extract.

Environmental water samples …

The Thermal And Photolytic Rearrangements Of Isatoic Acid Diazide, Ana Alejandre Ciereszko

Chemistry & Biochemistry Theses & Dissertations

The primary objective of this research has been the thermolysis and photolysis of isatoic acid diazide 1. Thermolysis in low boiling solvents produced the acylazido benzimidazolone 10, while refluxing in high boiling solvents gave rise to the imidazoindazoline 31, presumably via Curtius rearrangements.

Photolysis of the diazide in methylene chloride gave rise to two photo products, 10 and 31, while photolysis in tetrahydrofuran produced only 31.

A study of the spectral and chemical characteristics of these products have been carried out.

The Synthesis And Characterization Of The 2,2'-Bisacylazide Of 3,3'-Bipyridine, Magdy Adly Guirguis El-Fayoumy

Chemistry & Biochemistry Theses & Dissertations

The primary objective of this research has been the synthesis and characterization of a new heterocyclic diacylazide, the 2,2'-bisacylazide of 3,3'-bipyridine 19. This heterocyclic diacylazide has been successfully synthesized from the phenanthrolin-5,6-dione 14, and examined with regard to its.thermal and photolytic decomposition.

Thermal decomposition of this disacylazide seems to go by a double-barreled Curtius rearrangement leading to a series of pyridonaphthyridinone (20) compounds such as 22 and 29.

An initial study of the photolysis of this bisacylazide has been initiated to examine the possible formation of nitrene-type intermediates.