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Some Reactions of Phenothiazine and Its Derivatives Ralph Oliver Ranck Iowa State College

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Some Reactions of Phenothiazine and Its Derivatives Ralph Oliver Ranck Iowa State College Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1957 Some reactions of phenothiazine and its derivatives Ralph Oliver Ranck Iowa State College Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Organic Chemistry Commons Recommended Citation Ranck, Ralph Oliver, "Some reactions of phenothiazine and its derivatives" (1957). Retrospective Theses and Dissertations. 15134. https://lib.dr.iastate.edu/rtd/15134 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]. SOME REACTIONS OF PHENOTHIAZINE AND ITS DERIVATIVES by Ralph Oliver Ranck A Dieeertatlon Submitted to the Graduate Faculty In Partial Fulfillment of The Requirements for the Degree of DOCTOR OF PHILOSOPHY- Major Subject: Organic Chemietry Appro^d; Signature was redacted for privacy. ; p Work Signature was redacted for privacy. Head of Major Department Signature was redacted for privacy. Deab of^Graduate Goilege Iowa State College 1957 UMI Number: DP12919 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 DP12919 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 qo-too I s li c\ / TABLE OF CONTENTS Page INTRODUCTION 1 HISTORICAL 8 Reactione Involving the Imlno Nitrogen or Involving a Subetituent on the Nitrogen 11 Oxidation Heactlone 65 Nuclear Substitution Reactions 68 Preparation of Organoboronic Acids and Anhydrides 73 EXPERIMENTAL 83 Phenothiazine Derivativeo 83 General 83 Chemicale Apparatus II Inert atmosphere 85 Sodium amide and eodiophenothiazlne 85 Sodlophenothiamine In tetrahydrofuran 86 jtt-Butyll1thium 86 Miecellaneoitf 87 N-Subetituted phenothiazine derivatives 88 10-Allylphenothiazine 88 10-(^-Blphenylyl)pheno thiazine 89 Bie{10-phenotbiatInyl)benzene 90 JB,£'-Bie(lO-phenothlazlnyl)biphenyl 92 10-(2_-Bromobenzyl) phenothiazine 92 10-(|f-(7-Chloroquinolyl)] phenothiazine (attempted) 9lf 10-(ja-De cyl)pheno thiaz Ine 94 In liquid ammonia 9^ Using ether as a solvent for the halogen compound 95 In tetrahydrofuran 96 10-Ethylphenothiazine 97 10-(£-Nltrobenzyl)phenothiazlne (attempted) 98 Ill Page 10-(£~Nll;rophenyl)phenothlazlne (attempted) 100 10-(£-Nltrophenyl)phenothlazlne (attempted) 101 10-(^-Oo tadeoyl)phenothlazlne 101 In liquid ammonia using high-epeed agitation 101 Using various solvents for the halogen compound 102 Using tetrahydrofuran or ether for the halogen compound and replacing the ammonia with the same solvent 103 Phenothiamine:boron trifluoride complex 10^ In ether (attempted) lOk In benzene 105 10-(^-Phenylsthyl)phenothiazine (attempted) 105 10-(Phenylphenothiazine 106 • In tetrahydrofuran (attempted) 106 Using the no-solvent method 106 10-(/'-Phenylpropyl)phenothlazine (attempted) 10? 10-(2-Pyridyl)phenothiazine 108 In liquid ammonia (attempted) 108 In tetrahydrofuran (attempted) 108 Using kerosene as a solvent (attempted) 109 Using the no-solvent method 110 10-(2-Pyridyl)phenothiazine:boron trifluoride complex 111 10-(2-Quinolyl)phenothiazine 112 In tetrahydrofuran (attempted) 112 No-solvent method 113 10-{Triphenylmethyl)phenothiazine (attempted) 114 In tetrahydrofuran 11^ In liquid ammonia 115 10-(Y-Triphenyl8ilylpropyl)phenothiazine (attempted) 115 N-Substituted phenothiazine-5-oxide derivatives 116 l¥ Page 10-(ja-Deoyl) plienothlazlne- 5-oxlde 116 10-Ethylphenothla2lne~5-oxide 117 10-||,-0otadecylphenothlazlne-5-oxlde 118 lO-Phenylphenothlaaine-5-oxlde 119 10-(2~Pyridyl)phenothlaiilne-5-oxid« 119 N-Substltuted phenothlazine-5,5-dioxlde derlvatlTee 121 10-{|i-Deoyl)phenothlazine-5» 5--dloxid« 121 10-Ethylphenothlazlne-5» 5-dloxlde 122 10-(|i-0ctadecyl)phenothlezlne-5.5-dioxide 123 10-Phenylphenothla2lne-5» 5-filo*ide 123 10-(2-Pyridyl)phenothlazlne-5»5-dioxlde 124 10-(2-Pyridyl)phenothiazlne-l',5,5-trloxlde 125 N-Substituted phenothlazlnee with nuclear substitution 126 3-Bromo-lO-ethylphenothlazlne 126 3-Chloro-10-{n-decyl)phenothl&zlne 127 3-Chloi'o-10-ethylphenothia2lne 128 lO-(n-Decyl)phenothlazlne-4-carboxyllc acid 129 10-Ethylphenothlazlne-3-boronlc acid (attempted) 130 lO-Ethylphenothlazine-4-boronlc acid (attempted) 131 10-Sthylphenothlazlne-^-carboxylie acid 133 From lO-ethylphenothlazlne-5-oxlde 133 Fi'ora 10-ethylphenothiazlne using n-butyl alcohol as a catalyst Tattempted) 13^ I 3-Trlphenylellyl-lO-ethylphenothiazine (attempted) 135 Triphenylsilyl-10-ethylphenothlazlne (attempted) 136 Boronlc Acid Derivatives 137 General 137 Chemical8 137 Apparatus 138 Titration of boronic acids 139 T Page Preparation of tri-n-butyl borate 139 Trlinethyl borate "" iho MiBcellaneous l4l Simple boronic acids 142 BenEeneboronic acid 1^2 1-Butaneboronic acid 1^3 From n-biityllithium (attenuated) 1^3 From n-butylfflagneeium bromide iMh £-DlBethylaii!inobenKeneboronie acid/or anhydride (attempted) 1^5 ^Dimethylaainobenzeneboronic acid anhydride 1^8 o-Hydroxybenzeneboronic acid anhydride 150 ^•fith isolation by extraction with 10^ sodium hydroxide 150 With ieolation by evaporation of the ether layer 152 £~Hydroxybenzeneboronic acid anhydride 153 Froit! ra-bromophenol 153 From 2-(||~brofflophenoxy)tetrahydropyran (attempted) 155 2-Hydroxy-6~naphthaleneboronic acid 157 kzo boronic acida 159 £-(3-Borono-^hydroxyphenylazo)ben?.eneulfonic acid 159 2-?^droxy-5-(£-bromo phe ny1a zo)be n z e neboro nic acid 160 jg-(3-Borono~^hydroxyphenylaf.o)ben«oic acid 162 2-i^droxy-5-(o-nitrophenylazo)benzeneboronic acid ~ 163 2-I^droxy-5-(ptienylaEo)benseneboronic acid anhydride 165 Cleavage reactions vith n-butyllithium 168 vl Page Cleavage of benzeneboronic acid with five equlvalentB of n-butylllthlum at reflux for 1.5 hours 168 Cleavage of benzeneboronic acid vith three equlvalente of n-butyllithium 170 At rooffi temper&ture for 20 ainutee 170 At reflux temperature for 20 minutes 171 At -60 to -50® for 25 minutes 171 Cleavage of 51-hydroxybenzeneboronic acid anhydride "" 172 DISCUSSIOH 173 Phenothlazine Derivatives 173 H-Substitution reactions 173 N-Subetituted phenothiagine-5~oxid08 178 N-Substituted phenothlazine-5,S-^ioxides 180 N-Subatituted phenothiasines ^ith nuclear substltuents 181 Phenothiasine derivatives ae scintillators 186 Boron Derivative?? 188 Slaiple boronic acids 188 Azo boronic acids 193 Cleavage reactions of aromatic boronic acids with li-butyllithiuffi 195 Organoboron compounds in brain tuiaor therapy 198 Suggestions for Future Research 200 SUMMARI 203 ACKNOWLSMEMENfS 205 APPENDIX 206 1 IN-mODUCTION For many yeare, phenothiazlne and some of Its deriTatlTcs have been useful ae medicinal agente and have also found use in other fields. As examples, phenothiazine has been valuable as an anthelmintic,^*^ tuberculostatic compound,^ and in­ secticide.^ ^-Diethylaminoethyl lO-phenothiazinecarboxylatef *1 10-(2-diethylaminoethyl)phenothiaaine (Diparcol), 2-ohloro- 10-(3-dimethylaminopropyl)phenothiazine (Chlorpromazine)'' and 10-(2-diethylaminopropyl)phenothiazine® hare been found to prevent nicotine-induced convulsions; while several, such as A, Oellcers. Irztl. Forsch.. II, 139 (1951) [ki. Aa.* 12719 (19553 • D. Ul'yanov, Trudy Inst. Zq^ol.. Akad. NauK Kazakh. it Rt. i» Parazitol. 200 (19 53) [£i. As., ill* (1955^ . ^R. B, Griffiths, J. Pharm. and Pharroaool.. 6, 921 (195^). ^B. L. Freelander, Proc. Soc. Exptl. Biol. Med.. 57. 106 (19^). %. L. Campbell, W. N. Sullivan, L. E. Smith and H. L. Haller, J. Econ. Entomol.. ZL, 1176 (1937). ®R. Dahlbom, Acta Chem. Scand.. £» 879 (1953). See, R. Dahlbom, T. Edlund, T. Ekstrand and A. Katz, Arch, intern, pharmacodynamie. 90. 24l (1952). ^A. Balestrieri. Arch, intern, pharmacodynamie. 100. 361 (1955) [C^ A^. 773611955)]. ®V. G, Longo and D. Bovet, Boll, eoc. ital. biol. sper.. 612 (1952) 42, 509 (1955)J . 2 10-[(l-methyl-3-piperldyl)ffiethyl3 phenothlazine^ and 10-(2- dimethylaBilnoethyl)phenothlazlne {RP3015)i^^ show good local aneetiietlc properties. The 10-(2-dlethylamlnoethyl)- and 10-(2-dimethylamlnoethyl)phenothiazine are also used ae fungi- static agents. Both 10-(2-di!nethylamlnopropyl)phenothiazine (Promethazine)^^ and 10-[2(l-pyrrolldlnyl)ethyl] phenothiazine (Pyrrolazote)^^ have shown good antihistaminic properties. The Chlorpromazine which has "been mentioned above ie perhaps best known for ite use as a tranquilizing drug^^ and in the 15 treatment of certain mental disorders, Others, too numerous to mention, may be used for a variety of ailments, these falling Into such catagorles as urinary antiseptics, anti­ spasmodics, circulatory agents, anti-shock agents, anti- Inflammatory agents, and agents for the treatment of travel 9 0. Nleschulz, K. Popendlker and K. H. Sack, /jcznei- imsl-FaZBsii, it, 232 (195^)
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