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Some Derivatives of Phenothiazine Reginald David Nelson Iowa State College

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Some Derivatives of Phenothiazine Reginald David Nelson Iowa State College Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1951 Some derivatives of phenothiazine Reginald David Nelson Iowa State College Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Organic Chemistry Commons Recommended Citation Nelson, Reginald David, "Some derivatives of phenothiazine " (1951). Retrospective Theses and Dissertations. 13745. https://lib.dr.iastate.edu/rtd/13745 This Dissertation is brought to you for free and open access by the Iowa State University Capstones, Theses and Dissertations at Iowa State University Digital Repository. It has been accepted for inclusion in Retrospective Theses and Dissertations by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. NOTE TO USERS This reproduction is the best copy available. UMI SOME DERIVATIVES OP PHEKOTHIAZINE by Reginald David Nelson A Dissertation Submitted to the Graduate Faculty in Partial Fulfillment of The Requirements for the Degree of DOCTOR OP PHILOSOPHT Major Subject: Organic Chemistry Approved! Signature was redacted for privacy. n Charge of Major Work Signature was redacted for privacy. Head of Major department Signature was redacted for privacy. lean or Gradu^e Coliege Iowa State College 1951 UMI Number: DP12879 INFORMATION TO USERS The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleed-through, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion. UMI UMI Microform DP12879 Copyright 2005 by ProQuest Information and Learning Company. All rights reserved. This microform edition is protected against unauthorized copying under Title 17, United States Code. ProQuest Information and Learning Company 300 North Zeeb Road P.O. Box 1346 Ann Arbor, Ml 48106-1346 ACIOJOWLBDGMENT The author wishes to express his gratitude to Dr. Henry Gilman for his valuable advice# criticism and encouragement given throughout the course of this investigation. 7/0! ill TABLE OP CONTENTS Page I. INTRODUCTION 1 II. HISTORICAL 3 A. Ring Closure Reactions . • . 5 B. liuclear Substitution Reactions • . 18 C. Reactions Involving the Imino Qrovp, . 28 D. Reactions Involving the Sulfur Atom. • • 40 E. Physiological Properties of the 10*(Dlalkylaminoalkyl}phenothiazine Derivatives. 48 F. Dimetalation of Heterocyclic Compounds • 57 III. EXPERIMENTAL 61 A. Metalation of Some Derivatives with n-Butyllithiuitt Followed by Reaction with Benzophenone. 61 1. Of phenothiazlne to give 1- dipheny Ihy dro3cyme thy Ipheno- thiazlne . 61 2. Of 10-ethylphenothiazine to give 4-diphenylhydroxymethy1-10- etl^lphenothiazine 62 3. Of lO-(^J-diethylaminopropyl)- phenothTazine to give 4- diphenyIhydroxyme thy1-10- (X-diethylaminopropy1)pheno- thlazine .«... 64 4. Of 10-/^-(l-pyrrolidyl)ethyl7" phenothiazlne to ^ve 4-diphenyl- hydroxymetjtwl-lO-2^"(1-pyrrol- idyl)ethyl^henothiazin© and 4,6(?)-bis(diphenyIhydroxyme thy1)- ^ l-pyrrolidy 1)e thyl^- phenothlazlne. 66 B, Metalation of Some Derivatives with n-Butyllithium Followed by Carbonatlon . 68 Iv Page 1. Of 10-(^(-dieth,ylaralnopropyl)- phenothTaslne .68 2» Of lO-ethylphenothiajsine-5-oxide to give 10-ethylphenothiazine- 4-oarboxyXic aold 69 (a) At 0*. , 69 (b) At -20* 70 C, Preparation of 10»Substituted Pheno- thiaaine Derivativos 71 1. 10»(^-Diethylaiiiinopropyl)- phenothlazine •........••71 2, lO-Mothylphenothiaain®. 72 3. lO-Kthylphsnothlazine 73 (a) Xn bonzons ••«••.... 73 (b) Xn liquid aimaonla* ..... 74 4, lO-Benzylphonothlasiine 75 6, 10-Phenylph©nothia»in® (attempted) 76 (a) In jcylene 76 (b) In liquid ammonia* ..... 77 6, 10-(£-Tolyl)pheno thlazine 78 7, 10-(o-Tolyl)phenothiazine 79 8, lO-A^etylphenothiazine. 79 (a) Using acetyl chloride. ... 79 (b) Using acetic anhydride ... 80 9« lO-Chloroaeetylphenothiazine. • . • 80 10. lO-Dichloroacetylphenothiazine. • 81 (a) Using diohloroacetic acid anhydride *•••••• 81 (b) Using dichloroacetyl chloride ..........82 (c) An attempted preparation . • 83 (d) A second attempted preparation 83 11. lO-Fhenacetylphenothiazine 84 12. 10-(3-C arboxy-4-hydroxypheny1)- phenothiazine (attempted) ..... 84 13. 10-(3-Carboxy-4-nltropheny1) phenothiazine (attempted) ..... 85 (a) Using methyl 2-nitro«5- bromobenzoate • 85 (b) Using 2-nitro-5- bromobenzoic acid 85 14. £-(10-Phenothlazyl)benzene- suifonamide (attempted) 86 (a) Using £-bromobenzene- sulfonamide. ..••.... 86 V Page (b) Using £-iodob0nzene- aulfonamide 86 D, Preparation of Some Monoxidea and Dioxides •....«.••» 87 1, Phenothiazine-5-oxide» 87 8, lO-Methylphenothiazine-5-dioxide 88 (a) Using potassim permanganate. 88 (b) Using hydrogen peroxide . , 88 3r lO-Eth.ylphenothiazine-5-oxide. , 89 4. lO-Ethylphenothiazine-5-dioxide. • 90 5. lO-Acetylphenoth.iazine-5-oxide .. 91 (a) Using nitric acid , , . , 91 (b) Using hydrogen peroxide . • 91 6, lO-Aoetylphenothiaaine-5-dioxide 92 (a) Prom 10-acetylpheno- thiazine* 92 (b) Prom 10-acetylpheno- thiazine-5»oxide* . • . 93 7. 10-ChloroacotylphenothiaBlne» 5-oxide. 93 8, 10-Chloroacetylphenothiazine- 5->dioxide 94 9, lO-DichloroacetyIphenothiaz ine- 5«dioxide* 95 10. The attempted nitric acid oxidation of 10-dichloro- acetylphenothiazine. ....... 96 11. 10-Phenacetylphenothiazine- 5-oxide. 97 (a) Using nitric acid 97 (b) Using hydrogen peroxide . 97 12. 10-Phenacetylphenothiazine- 5-dioxide 98 (a) Prom lO-phenacetyl- phenothiazine ....... 98 (b) Prom 10-phenacetyl- phenothiazine-5«oxide ... 99 E. Miscellaneous Reactions. ........ 100 1. Preparation of ^-diethyl- aminopropyl chloride ....... 100 2. Hydriodic acid cleavage of the crude carbonation product from 10-(^-diethylaminopropyl)- phenothiazine to give m-carbo3ty- diphenylamine 101 vi Page 3, Hydrolysis of 10-acotylpheno- thiasine-S^oxide • * 103 4, Hydrolysis of 10-acetylpheno- thiasina-S-dioxide 103 5, Attempted nitration of ethyl m-iodobenzoate 103 6, Treatment of the product from the attempted nitration of ethyl ra«iodobenzoate with sodium %droxide 106 7, Attempted nitration of m- iodobenzoic acid . 106 8, Dehalogenation of the product from the attempted nitration of m-iodobenzoic acid 109 9* %drolysis of the product from the action of nitric and sulfuric acids on m-iodobensoic acid, • . 109 IV. DISGUSSIOH Ill A, Metalation Reactions of Phenothiaaine and Some of Its Derivatives. Ill B, Preparation of Some 10-Substituted Phenothiazines 118 0. Oxidation Reactions 134 D. Attempted Nitration Reactions. ..... 138 £. Research Suggestions . 135 V. SUMMAIK. 139 -1- I. INTRODUCTION The earliest studies on the physiological action of the phenothiazine derivative methylene blue, by Guttmann and Ehrlich#^ showed that this compound had a specific action in human malaria. Not until forty-three years later was it discovered, in connection with the investigation of the toxicity of organic sulfur compounds to mosquito larvae, that phenothiazine possessed insecticidal properties. Ad­ ditional research later revealed that phenothiazine itself is also useful as a larvicide, fiangicide, bactericide, parasiticide, urinary antiseptic, anthelmintic agent and an antioxidant. In contrast to its high toxicity to lower forms of life, phenothiazine possesses a low toxicity to man and other higher forms of animal life. These discoveries, as well as its low cost of production, make phenothiazine a very useful compound. Currently, considerable interest is shown in pheno­ thiazine derivatives because of the discovery by Halpem,^'^ 5*— P. Guttmann_and P, Ehrlich, Berlin, klin. Wochschr., 593 (1891), /Chem. i^entr., 65, I, 321 Ue§2)'y\ ^F, L, Campbell, W, N, Sullivan, L, E, Smith and H. L, Haller, £, Scon# Entomol., 27, 1176 (1934), N, Halpem and R, Ducrot, Compt, rend, soc, biol., 140, 361 (1946), N, Halpem, J, Allerpcy, 18, 963 (1947), that certain 10-(dialkylaiainoalkyl)phenothia2ines are very active antihistaminic agents possessing a low degree of toxicity toward the host, A niomber of these derivatives also exhibit antianaphylactic, local anesthetic# anticonvulsant and antinicotinic action, A more detailed discussion of these properties will be given in a later section of this dissertation* The purpose of this investigation has beenJ (1) to study further the metalation of phenothiazine derivatives with the view in mind to use this reaction aa a means to introduce various substituents into the benzene nuclei; (2) to modify the structure of certain dialky1aminoalky1 derivatives and thereby compare the effect of changing the molecular structure on the physiological properties; (3) to extend the application of sodamide as a condensing agent in the preparation of 10-aubstituted phenothiazines; (4) to prepare various 10-acyl derivatives; and (5) to develop satisfactory methods to oxidize the sulfide linkage of the various derivatives to the sulfoxide and the sulfone, re­ spectively. II. HISTORICAL A study of the chemistry of phenothlaain© and its de­ rivatives was initiated in 1803 by August Bemthsen® who suspected that the phenothiazine nucleus was present in methylene blue* In his series of experiments# he success­ fully determined the structure of both metl:^l©ne blue and phenothiazine; the latter is given below with the numbering system in current use by Chemical Abstracts. The
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