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Comparison of Phenanthridine with Other Aza-Aromatic Heterocycles " (1956)

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Comparison of Phenanthridine with Other Aza-Aromatic Heterocycles Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1956 Comparison of phenanthridine with other aza- aromatic heterocycles John Joseph Eisch Iowa State College Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Organic Chemistry Commons Recommended Citation Eisch, John Joseph, "Comparison of phenanthridine with other aza-aromatic heterocycles " (1956). Retrospective Theses and Dissertations. 12752. https://lib.dr.iastate.edu/rtd/12752 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 GOMPARISON OF PHEilNTHEIDIME WIfH OTHER IZ^-lROMAflC HEfEROCXCLlS John Joseph Eleoh. A Dissertation Subffiltted to tti« &rattiat@ Faculty in Partial Fulfillatnt of The lequlrementB for the Degrs© of DOGfOR OF PHILOSOPIff Major Subjeet! Organ!© Chemistry ApproTed: Signature was redacted for privacy. In Charge of Major Work Signature was redacted for privacy. lead of Major .D©p&rtkent Signature was redacted for privacy. Dean of Graduate College Iowa, State College 1956 UMI Number: DP12078 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 DP12078 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 11 TABLE OF CONTENTS Page I. iMTHOroCTION 1 II. HISTORICAL—COMPIRISOS OF PHEMASTHRIDIHE WITH OTHER AZA-AIOMATIG HSTEHOCYGLES ^ A. Introduction ^ B. Aroiiatloltj 6 C. Theoretiosl Vlewi of the ChemlBtry of Aza- arofflatie Systtme 11 1. Gentral eonsIdtrations 11 2. Bond fixation 12 3. Qu&ntim ffltehanical treatment of az«- aroa&tlc heterocyclee 15 4-, Transition etrnt® tre&tnent of aromatic tubetitmtion 25 D. Factors Affecting the Mod® of Attfl,ck on Aza-aromatic Systems 31 1. Speeiee undergoing attack 31 2. Attacking species 3' 3. ReTersibility 3' 4. Sutoetitutnti 35 5. Catalysts 36 6. Temperature 37 7. Bol^ent 38 E. Ghemioal Propertlte 39 1, Substitution reactions 39 2, Eleetrophilie eubetitution ^1 a. Hitration 4l b. Halogenstion c. Siilf©nation 46 d. Mercur&tlon 47 e. Friedel-CraftB alkylation 49 3, Kucleophlllo substitution 49 T1&0S4 111 a. llkflatloti b, Affilnatlon e* Hydride loii reduction d, fiyiroxylatlon e. Gyanatloii 4. Free radical ewbstltutlon a. Pfetnylatlon to. Methylatlon e. Reduction €, Coupling e. High teaperature reactions 5. Mdltlon reactions a. Hydrogenetlon b. Reaction with dlalkyl aeetylene- dl0arbo:H:ylst© e. iltrogen coaplexts l) M-Oxldts 11) Q.mternlzation ill) Salt foraatlon 6. Ring stability ?•, Coaparlson of characteristic derlvatl-ree a« iBiln© derlT&tlveB b, Carboxyllc acid© 0. Dlhydro derivatives d. Halogen derivatives e, %droxyl derivative! f» Methyl derivatives g. l-Oxldes P. Phyelcal Properties 1. Molecul&r diffleneloM 2. Molar refraction. 3. Dlpol® »omente Infrared epectra 5. Ultraviolet spectra 6. fh.©rnioch«ailcal data CI, PhyBlological Properties Iv Page III. IXPSRIMEMTAL 95 A. Preparation of Biphenyl Intermediates 95 1. 2-lc®t&rol!iio'blplaenyl 95 2. 2-AcetaninO'-5-'bro»ot>lphen|'l 96 3. 2-Ac®tamiiio*.^'-cli,loroblpfeenyl 97 k, 2-AHilno-2'-nltrot!lpfa#n.yl 98 5. 2-Ac@taiilii©--2'-!iitro'biphenyl 99 6. 2-lcetamino-3-iiltroblplien|'l 99 7. 2-BiityraiilnoMph.eEyl 100 8. 2-Valeramln©Mph©nyl 101 9. S»i•-Dl(£-E€Ryi) oxalaMlde 102 B« Phenanthrldlne Derl?atlTes by Cycllzatlon IO3 1. 6-||-Propylphsnsiitlarltiiie 103 2. 6-|i-Butylpiien«nthrldla@ 104 3. 2-BroiBo-6-o@tliylpiienantferl<ilne 105 k, 6-Ketl^l-^-niltropfa.enanthrldlne 105 5. 6-Metjhyl-lO-iiitropiienanthriaine 106 6. 6,6'-Diplienaatlari<ayl (attsapted) 106 a# Phoipfaome oxychlorlde and nitrobenzene 106 b. Polypbosphorlc acid I07 C. Chemletry of tiie Pfaenatittirldine System 107 1, Allylfttlon and arylation I07 a. 6-n~ButylpJEienantta*idine 107 , b* g-^-Propylpiienanthrldlae 109 c. e-^-folyl-Sfe-dihydrophenanthridlne 110 d. Defeydrogiinatlon of 6-o-tolyl-5»6~ dlhydrophenanthrldlni" 111 e. 6-Bsnzyl-5»6-<iibydropiienanthridin© 112 f. 6-BenEoylplierianthridlne 113 g. Bls-6-plienylphenantiarldlne 113 2. Broffllnation 11^ a, M-Broaoeuocinloilde method 11^ b. Phenanthrldine hydrobroialde per bromide metbod 116 o, Bronlne-glaclal aeetlc acid aethod 117 T Page d, Broalne-carbon tetraehlorlde method (attettpt®d) 118 e, OxlAatlon of the wnkriown browophenanthridlne 118 f, 2-CfanoplieiianthrldlHe 119 3. Gyanatlon 120 a, Phenanthridine methlodldt 120 to. 6- Cyano-5*-o®thyl- 5 # 6-aihydrophen- antbrldiiit 121 e. 6-C|-aftopli@n&»thrldlne nethiodidt 121 4. Prled©1-Grafts reaction (attempttd) 122 5. Hydroxylation 122 6. 2-Mltroph@nianthpldln® 123 7. Oxidation 125 a. Oxidation ©f phenanthridlne (attempted) 125 Oxidation of 6-ja-batylpherianthrldlne 125 G. Oxidation of &-n-propyiphenanthrldine 12? d, ^-Nitrophenanthrldone 128 e, 10-Sltroplie:ii&athrldoB« 128 f, 2-BroBopheRaiithrldon® 129 8. Sulf©nation 130 a. Trial 1 I30 to. Trial 2 132 D. Chemietry of Phenanthrldone 132 1. Acetylatlon Cattenpted) 132 2. Broolnation 133 3. Ohlorlnatlon 13^ k, lodinatlon • 136 5. Mercwratlon (attempted) 137 6. lltratlon 137 7. Sulf©nation 139 8. Heaotion with ||-toutyllltfe.iuii l4l 9. Reaction with phoephortas pentaohlorlde 1^2 E, Chemistry of Phenanthrldone Derivative® 1^3 1. 2-Ac@t&ainophena.nthridone 1^3 2, Broffllnatlon of 2-a.cetafflinophenanthridone 143 Tl Page iitrntlon ©f 2*aceta©lnoplieiianthridone i 2-Glilo3ro- 5--ffl®tlijlplienaiitiirl<ione 1^5 5. 5-Mei;%l-2-alt3?oph®nantiirldone 6. 2-Bi*oao~#-.Bltrop,isitn&ntferid6ii© 1^7 7. 2-CihloTO-^-niti'ophenaathriaone 1^8 8. lltratlen of Z-iodophenanthrldon® 1^9 9. Reaetlon ef a-feroiaophenanthriaoae with jft-.butylllthl«a 1^9 F. Reaetlon of Allylmagnesiuii Bromide with the AzometblEe Linkage 1,51 1, General prooedwre for the intera-ctlon of nitrogen heterooyolee with allylaagneslwffl broffilde 151 &. 4-Allylpyrldln« 153 to* 6-lllfl-5»6-dihytr©phenaiithrMine 15^ 00 -.lliyltoensylanlllne 156 d. 9»Allyl»9»10-dihydro&eridine 156 •©* 2,3-l3iallyl-l,2,3,^-tetra.hyaroquinoxallne 157 f, cL -Mlylfeenthydrylaalllnt 15© 2. Strwctiaral proofs of tb® products 159 a» 2-Allylpyrld.in@ 159 1) Meth©5 1 159 11)-lethod 2 160 b* HyflrogenatioR of 4-allylpyrldlne 161 c. 'Mehrottate oxidation of 6-allyl-5»6- dlhydreptosnanthridine 162 d* Bichromate oxidation of 9-allyl-9»10- dl%!lr©acrldiiit 162 t* Heaetlon of jj-pi'ppyllithiuffl with benzophenone" anil C n-propyl) benzhydrylanllin©) 163 f. Reduction of the hydrolyzed allyl Q-rignarfl adduct of benzophenone anil CeonTersion of oc-ftllylbenzhydryl- anlline to oc. -Cn-propyl) benshydryl- anlllne 16^ g. Butyrophenone 16^ Til Page ii, Butyrophensne anil 165 i, Propyl) benzhydrylaniline 166 &, •Gheo.lstry of Qtiinolin© and leoqwinoline Derivativei 16? 1. Trl|)lienyl-3-qain0lyltln 168 2. lBoqulnoline-4-e»rl303cylio acid 17O 3. ^-BenEoylisoqulnQlin© 170' I¥. DISCUSSlo» 173 A. General Gonsideratidng 173 B. Chemistry of the Phtnanthridine System 176 1. Hucleophilic rtagente 176 a* Alkylation and arylation 176 b. Cyanation 181 e. Hydroxylation 182 2. Sltctrophilic reagents 183 a, Brofflination 183 b, BTitration 185 c, Siilfonation 186 3. Diehromste oxidation of S-alkylphenanthri-" dines 187 C. Cheaiitry of the Phenanthridone Byetem 190 D« Chenistry of Phenanthridons Derivatives 195 1. iitratlon of a-subst Ituted pbjenanthridones 195 2. Alkylation of gubetitated phenanthridones 196 3. Halogen-aet&l interconversion with 2-broffioph®n&nthridone 197 E, Synthesis of Phenanthridine DerivativeB 197 F. Beaction of Allylmagnesluai Broiaide with tte Asoo®thine Linkage 200 Y. BIMMARJ 207 vill Page ¥1. LlflRATtmi eiTED 211 ¥11. ACIIOILEKJMEMT 225 1 1. IlTRODUCflOi Althowgh ptenantfarldine, a nitrogen iieterocjcle Iso- sterlc with pJtenanthrene, le one ©f th© constltuentt of coal tar CD, it was flr«t ©btalned in 188^ toy dr&ebe (2) when h® pag®ed henmlmlllm through a r®€-hot tutoe. Th© char&o- terlzatlon of this iinkn0%''n hage was gtihieqaently accoHiBllshed toy Pictet and Ankerimlt (3) la 18S9. Pictet and his group (^-10) studied thlg eystea during the -next 15 yeare, but the field tl»n lay doraant until 193® when the dlscoTery of a benzophenanthrldlne nucleus in eertain alkaloids luch a® chelldonin© and, Banguinarlne reaw^ened interest In phen- anthrldlne {11). Shortly thereafter, Morgan and Wall® began their fruitful- reeeareht® on the fundamtntal eheraletry of phenanthrldlne *Mch In tl»e led to the dlteoTery of deriva- tivee effectlv® against trypanosomlaelis in anlaal® and children (12-20), Despite the aiaple literature published on phenanthrldlne derivatlTes, our knowledge of the fundamental ohenilftry has progrtised little from tjto.t established by the work of Morgan and WallB
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