FIRST INTERNATIONAL CONGRESS OF HETEROCYCLIC CHEMISTRY

THE UNIVERSITY OF NEW MEXICO, ALBUQUERQUE, NEW MEXICO

JUNE 12-15, 1967

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General Chairman

Raymond N. Castle

Advisory Committee

Editorial Board of the Journal of

 

Heterocyclic Chemistry

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P R O G R A M

Welcome and Introductory Remarks

Raymond N. Castle

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INVITED LECTURES

Monday, June 12, 9:00 A.M.                                                                New Mexico Union Ballroom

William W. Paudler, Athens, Ohio

Some Aspects of the Chemistry of Di- and of Poly-azanaphthalenes

H. Daub, Moderator

Monday, June 12, 10:30 A.M.                                                              New Mexico Union Ballroom

R.. Huisgen, München

1,4-Dipolar Cycloaddition, a General Principle of Heterocyclic Synthesis

N. H. Cromwell, Moderator

 

Tuesday, June 13, 9:00 A.M.                                                                 New Mexico Union Ballroom

A.. R.. Katritzky, Norwich

The Steric Requirements of sp2 and sp3 Hybridised Lone Electron Pairs in Heterocycles

F. D. Popp, Moderator

Tuesday, June 13, 10:30 A.M.                                                             New Mexico Union Ballroom

Edward C. Taylor, Princeton, New Jersey

Unequivocal Syntheses of Heterocyclic N-oxides

E. F. Elslager, Moderator

 

Wednesday, June 14, 9:00 A.M.                                                          New Mexico Union Ballroom

Martin J. Weiss, Pearl River, New York

Some Topics in Indole Synthesis

Y. Ban, Moderator

Wednesday, June 14, 10:30 A.M.                                                          New Mexico Union Ballroom

D. J. Brown, Canberra

Quantitative Aspects of Nucleophilic Replacements in the Pyrimidine and Some Related Series

C. C. Cheng, Moderator

Thursday, June 15, 9:00 A.M.                                                                New Mexico Union Ballroom

George deStevens, Summit, New Jersey

New Seven-membered Cyclic Systems with One, Two and Three Nitrogen Atoms in the Ring

A. I. Meyers, Moderator

Thursday, June 15, 10:30 A.M.                                                              New Mexico Union Ballroom

Wolfgang Pfleiderer, Stuttgart

Reactivity and Heteroaromatic Character of Six-membered Nitrogen Heterocycles

R. K. Robins, Moderator

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CONTRIBUTED PAPERS

Monday, June 12

 

SECTION A: Jesse LeRoy Riebsomer Memorial Session                                            Education 103

Presiding, R. N. Castle

1:30                 1.  Leroy B. Townsend, Robert J. Rousseau, and Roland K. Robins. The Preparation of Some New 4,6-Disubstituted Imidazo[4,5-c]pyridines (3-Deazapurines).

1:50                 2.  Robert J. Rousseau, Roland K. Robins, and Leroy B. Townsend. The Synthesis of 7-β-D-Ribofuranosylpurines, β-Anomers of the Pseudo-Vitamin β12 Purine Nucleosides.

2:10                 3.   A.L. Meyers, S. Singh, and A. H. Reine. The Chemistry of Heterocyclic Enamino-ketones.

2:30                 4.   Darrell E. O'Brien, Louis T. Weinstock and C. C. Cheng. Pyrimido[4,5-b] quinolines.

2:50                 5.   D. K. Wall, J-L. Imbach, A. E. Pohland, M. C. McMaster, R. C. Badger, and N. H. Cromwell. A Novel Base Catalyzed Dehydrogenation-Rearrangement of 2-Phenyl-3-aroylaziridines

3:10                 INTERMISSION

3:30                 6.   Y. Ban, T. Oishi, M. Nagai, T. Ohnuma, and Y. Sendo. Studies on the Synthesis of Some Indole Alkaloids through the Common Intermediate.

3:50                 7.   Edward F. Elslager, Donald F. Worth, Neil F. Haley, and S. C. Perricone. Novel Heterocyclic Compounds Derived from 1,2,4,5-Tetrahydro-3H-benzo[2,4]diazepine-3-thione.

4:10                 8.   Ludwig Bauer and C. S. Mahajanshetti. Pyrazolo-N-hydroxyuracils from the Modified Lossen Rearrangement of vicinal Pyrazoledicarbohydroxamates.

4:30                 9.    F. D. Popp and J. M. Wefer. Reissert Compound Chemistry.

4:50                 10.  Hirotaka Murakami and Raymond N. Castle. Imidazo[4,5-c]pyridazines.

 

SECTION B: Presiding, E. Campaigne                                                                        Education 101

1:30                 11.  E. Campaiqne, H. R. Burton, and C. D. Blanton. Synthesis of New Heterocyclic Systems via Ylidenemalononitrile Cyclization.

1:50                 12.  L. H. Klemm,and C. E. Klopfenstein. Direct Substitution into the Thieno-pyridine Nucleus.

2:10                 13.  Reinhard Zell and L. H. Klemm. Synthesis and Transformations of 5-Acetylthieno [2,3-b]pyridine.

2:30                 14.  D. R. McCoy and L. H. Klemm. Sulfur Insertion into Biaryl, Aryl-azarene, and Biazaryl Compounds.

2:50                 15.  D. E. Boswell, J. A. Brennan, P. S. Landis, and P. G. Rodewald. 2-,3-,4-,5-,6-, and 7-Nitrobenzothiophenes.

3:10                 INTERMISSION

3:30                 16.  Daniel L. Klayman and George W. A. Milne. The Reaction of 2-Amino-2-thiazoline with Phenylisothiocyanate.

3:50                 17.  M. Wilhelm and P. Schmidt. Synthesis and Reactions of 1,4-Benzothiazines.

4:10                 18.  Earl M. Hoerger. An Apparent Aza Analog of a Thiothiophthene.

4:30                 19.  Vincenzo Bertini and Piero Pino. Synthesis of 1,2,5-Thiadiazole and 1,2,5-Selenadiazole Derivatives and their Reactions with Nucleophilic Agents.

4:50                 20.  Shelby F. Thames and Josef E. McCleskey. Silicon Substituted Heterocycles: A Novel Synthesis of N-Silyl-substituted Ethylenimines.

 

SECTION C: Presiding, R. E. Partch                                                                              Education 104

1:30                 21.  E. Marcus and J. K. Chan. Novel Condensation Products of Diketene.

1:50                 22.  H. G. Pars, F. E. Granchelli, J. K. Keller, R. K. Razdan, S. Van Horn, and D. Hunneman. Nitrogen Analogs of Tetrahydrocannabinol.

2:10                 23.  Leonard R. Worden and Kurt D. Kaufman. Synthesis of Benzo-[1,2-b,5,4-b']difuran: a New Synthesis of Psoralene.

2:30                 24.  Johann F. Klebe and Herman Finkbeiner. Rearrangements and Reactions of 2-Sila-oxazolidones.

2:50                 25.  Akira Takeda and Sigeru Torii. The Nitrosation of γ-Dialkyl-α-carboxy-S- carb-ethoxy-β-butyrolactone.

3:10                 INTERMISSION

3:30                 26.  Richard E. Partch. Model Studies on Salamander Alkaloids: 6-Aza-8-oxabicyclo-[3.2.1]octane Derivatives.

3:50                 27.  J. Ernest Simpson, Guido H. Daub, F. Newton Hayes, and Juan Yguerabide. Liquid Scintillators. The Synthesis and Properties of Some Dibenzo- and Dinaphtho-dioxepins, dioxocins, dioxonins, and dioxecines.

4:10                 28.  S. Morrocchi and A. Ricca. The Catalytic Action of Boron Trifluoride in Cyclo-additions Leading to Five-membered Heterocycles.

4:30                 29.  W. I. Awad and A. F. M. Fahmy. Studies on Azidolysis of Oxazolones (Part II).

4:50                 30.  P. Rajagopalan and C. N. Talaty. A New Synthesis of the 1,4,2-Oxathiazine Systems.

 

SECTION D: Presiding, M. Israel                                                                                Education 105

1:30                 31.  D. A. Nelson and J. J. Worman. Reactions of 1,5-Diphenyl-3,7-Dibromo-Octahydrodiazocine (I).

1:50                 32.  T. A. Dobson, M. A. Davis and A. Hartung. A Novel Synthesis of the 10,5‑(Iminomethano)-10,11-dihydro-5H-dibenzo[a,d]cycloheptenes Ring System.

2:10                 33.  R. Ian Fryer, J. V. Early and L. H. Sternbach. A Rearrangement of a 5-Phenyl-1,4-benzodiazepine Derivative.

2:30                 34.  E. E. Garcia, J. G. Riley and R. Ian Fryer. The Synthesis and Transformations of 5-(3-Indolyl)-2,3-dihydro-1H-1,4-benzodiazepines.

2:50                 35.  Mervyn Israel, S. Karin Tinter, Dorothy H. Trites, and Edward J. Modest. Synthesis and Chemistry of Isomeric Dihydropyrimido[4,5-b][1,4]diazepinones.

3:10                 INTERMISSION

3:30                 36.  R. J. Dubois and F. D. Popp. Some Chemistry of the 11H-Dibenzo[c,f][1,2] diazepine System.

3:50                 37.  William J. Houlihan and Robert E. Manning. Synthetic Approaches to Medium-Size Rings Containing Nitrogen.

4:10                 38.  Madeleine M. Joullié and George Slusarczuk. Synthesis and Properties of Fluorine-Containing Heterocyclic Compounds.

4:30                 39.  A. Stempel, I. Douvan, and L. H. Sternbach. Quinazolines and 1,4-Benzodiazepines XXXIV. 4,1,5-Benzoxadiazocin-2-ones, A Nove1 Ring System.

4:50                 40.  Harkishan Singh, Veerendra V. Parashar, and T. K. Kaw. Studies on the Synthesis of 3,17α-Diaza-A,D-Bishomoandrost-4α-ene-4,17-dione.

 

Wednesday, June 14

 

SECTION A: Presiding, T. Kametani                                                                          Education 103

1:30                 41.  Hideo Kanō, Yuzo Nakagawa, Hirozo Koyama, and Yoshiko Tsukuda. Structure of a New Class of C-Nucleoside Antibiotics, Showdomycin.

1:50                 42.  Richard L. Tolman, Leroy B. Townsend, and Roland K. Robins. The Synthesis of Certain Tri-substituted Pyrrolo[2,3-d]pyrimidines and the Corresponding Ribosides.

2:10                 43.  Brian M. Lynch, Allan J. Robertson, and John G. Webb. Kinetics of Nucleophilic Substitutions in Purine Analogs.

2:30                 44. R. F. Borne, M. P. Mertes, and L. E. Hare. Synthesis of Furo[2,3-c]pyridine Derivatives.

2:50                 45.  Norbert Isenberg and Charles Heidelberger. 5-Carboxy-2'-deoxyuridine.

3:10                 INTERMISSION

3:30                 46.  Tetsuji Kametani and Hiroshi Sugahara. The Reaction of 2-Nitro-1-indanone Oxime with Polyphosphoric Acid.

3:50                 47.  R. John Stedman, Larry D. Davis, Libby S. Miller, and John R. E. Hoover. Acylation of 2-Aminobenzimidazoles: Spectra and Structure of Products.

4:10                 48.  To be announced.

4:30                 49.  Robert E. Harmon and Jack L. Parsons. Ring-Chain Tautomerism of Tetrahydro-pyrimido[4,5-d]pyrimidines.

4:50                 50.  S. Hauptmann, H. Wilde, and K. Moser. A New Synthesis of 1-Amino-4-aryl-1,2,3-triazoles from Aryldibromomethylketones.

 

SECTION B: Presiding, G. M. Singerman                                                                   Education 101

1:30                 51.  I. M. Goldman. Novel Transformations in the Pyrimidobenzothiazine Series.

1:50                 52.

2:10                 53.  M. S. Manhas and Ajay K. Bose. Synthesis of Some Penicillin Analogs.

2:30                 54.  John J. D'Amico and Robert H. Campbell. Derivatives of Potassium Cyanodithio-imidocarbonate 1. Synthesis of 1,4,6,9-Tetrathiaspiro[4.4]nonane and Related Compounds.

2:50                 55.  David B. Capps and Patricia S. Charlton. Synthesis and Reactions of N-(Heteroaryl) lactams.

3:10                 INTERMISSION

3:30                 56.  Joseph E. Dunbar and Betty H. Tarnowski. Reaction of the Thiolsulfonate Group with the Aromatic Nucleus: A New Ring Closure.

3:50                 57.  Moshe Avramoff. The Synthesis of 5,5'-Dinitro-2,2'-hydrazothiazoles, a New Type of Potential Chemotherapeutic Agents.

4:10                 58.  Herman Finkbeiner and Johann F. Klebe. Formation of Silaoxazolidones from Substituted α-Amino Acids.

4:30                 59.  J. Goerdeler. Cyclo-1,4-additions of Acyl-Isocyanates and -Isothiocyanates.

4:50                 60.  Haruyuki Watanabe, Tetsushi Totani, and Masaji Kubo. NMR and Vibrational Spectra of l0B-Enriched N-Trimethylborazine.

 

SECTION C: Presiding, L. B. Townsend                                                                    Education 104

1:30                 61.  J. L. Pinkus. The Thermal Rearrangement of 3-Carbonylsubstituted-2,1-benzisoxazoles to 2-Substituted-3,1,4(H)-benzoxazones. Application of Combined Gas Chromatography-Mass Spectrometry.

1: 50                62.  J. L. Pinkus and R. M. Gerkin. The Structure of Homoanthroxanic Acid.

2:10                 63.  J. L. Pinkus, M. Sax, J. Pletcher, D. Scholtz, and R. M. Gerkin. The Structure of 2-Phenylisatogen N-Oxime; the Crystal and Molecular Structure of the 4-Bromo-benzoylation Product of 2-Phenylisatogen N-Oxime.

2:30                 64.  W. P. Cullen, D. M. X. Donnelly, D. P. Melody, and E. M. Philbin. Oxidation of α-Substituted Chalcones.

2:50                 65.  G. Bianchi, G. Gandolfi, and P. Grünanger. On some Reactions of 5-Acyl-2-isoxazolines.

3:10                 INTERMISSION

3:30                 66.  Richard E. Partch. The Role of Heterocyclic Bases in Lead IV Organic Chemistry.

3:50                 67.  P. Bravo, G. Gaudiano, C. Ticozzi, and A. Umani-Ronchi. Synthesis of Five-membered Heterocycles by Sulphur Ylides.

4:10                 68.  H. Wamhoff. Synthesis of Heterocyclic Compounds by Interception Reaction of Opened α-Acyl Lactones.

4:30                 69.  Sven-Olov Lawesson. Synthetic Routes to Heterocyclic Compounds via Enamines.

4:50                 70.  H. Smith Broadbent, Richard K. Olsen, Richard M. Sheeley, and Weldon S. Burnham. Novel Heterotricyclic Systems: 2,7-Oxa-,Thia-, and Aza-10-azatricyclo-[5,2,1,04,l0]decanes.

 

SECTION D: Presiding,  D. E. O'Brien                                                                       Education 105

1:30                 71.  Alfred Hassner and Frank W. Fowler. The Synthesis and Reactions of 2H-Azirines.

1:50                 72.  Ronald A. Mitsch. Synthesis of Fluorodiazirines, Diaziridines and Aziridines.

2:10                 73.  Ronald A. Mitsch. The Nucleophilic Ring Opening of Difluorodiazirine. The Formation of N-Cyanophosphorus Imides and Difluorophosphoranes.

2:30                 74.  Roger D. Westland, Richard A. Cooley, Jr., Mary L. Mouk, and Joyce L. Holmes. Preparation of 1-Alkylaziridines by Direct Alkylation of Ethylenimine with Alkyl Halides.

2:50                 75.  John C. Stowell.1,2-Diazetidinediones.

3:10                 INTERMISSION

3:30                 76.  Emil J. Moriconi, John F. Kelly, Wheeler C. Crawford, Walter C. Meyer, and James McG. McCrae. β-Lactams. The Reaction of Chlorosulfonyl Isocyanate with Strained Olefins and Bicyclic Systems.

3:50                 77.  Marvin Charton. Annular Tautomerism in Nitrogen Heterocycles. III. Cinnolines.

4:10                 78.  Paul Friedman. A Semi-Empirical SCF-LCAO Study of Thialene, Isothialene and Cycloheptathiete.

4:30                 79.  Pankaja K. Kadaba. Solvation Effects in 1,3-Cycloaddition. Reactions.

4:50                 80.   M. J. Nye and W. P. Tang. Tautomerism of 3,5-Diphenylpyrazol-4-ol.

 

Thursday, June 15

 

SECTION A: Presiding, L. D. Hansen                                                                         Education 103

1:30                 81.  J. Howard Rytting, James J. Christensen and Reed M. Izatt. pK, ΔHo and ΔSo Values for Proton Ionization from Several Pyrimidines and their Nucleosides.

1:50                 82.  David M. Grant and Ronald J. Pugmire. Use of Carbon-13 Magnetic Resonance Technique in a Study of the Electronic Structure of Heterocyclic Molecules.

2:10                 83.  David M. Grant and Ronald J. Pugmire. Charge Polarization and Bond Orders in Nitrogen Heterocycles.

2:30                 84.  L. Paoloni, M. L. Tosato, and M. Cignitti. Physico-Chemical Studies on the Methyl Derivatives of Cyanuric Acid and Trithiocyanuric Acid.

2:50                 85.  B. Pullman. Molecular Orbital Studies of the Electronic Structure of Biological Purines and Pyrimidines.

3:10                 INTERMISSION

3:30                 86.  T. A. Crabb and R. F. Newton. Configurational and Conformational Studies with Methyl Substituted 8-Thia-l-azabicyclo[4.3.0]nonanes.

3:50                 87.  L. D. Hartung, W. R. Leverich, and H. J. Shine. The Reactions of 2,2'-Hydrazodiphenylmethane in Acid Solution.

4:10                 88.  Hermann O. Wirth, and Emily B. White. Syntheses and Properties of 2-Arylindoles.

4:30                 89.  Henning Lund. Controlled Potential Electrolysis of some Heterocyclic Compounds.

4:50                 90.  L. D. Hansen, B. D. West, E. J. Baca, and C. L. Blank. Thermodynamics of Proton Ionization from some 1,2,3-Triazoles.

 

SECTIONB: Presiding, W. J. Haggerty, Jr.                                                                 Education 101

1:30                 91.  R. A. Abramovitch, G. A. Poulton, and Choo-seng Giam. Some New Aspects of Nucleophilic Aromatic Substitution in the Pyridine Series.

1:50                 92.  Choo-seng Giam. Some Aspects of the Chichibabin Reaction.

2:10                 93.  Ludwig Bauer, Thomas E. Dickerhofe, and Fred M. Hershenson. Substitution of Pyridinium Salts by Mercaptans.

2:30                 94.  A. E. Kelley and E. K. Moss. Base-Catalyzed Hydrolysis of Pyridinium Salts.

2:50                 95.  William J. Haggerty Jr., and C. C. Cheng. Synthetic Approaches to Azapyridoxines.

3:10                 INTERMISSION

3:30                 96.  Robert K. Howe and K. W. Ratts. Some Reactions of Pyridinium Ylids.

3:50                 97.  Arnold T. Nielsen and Ernest N. Platt. Hydroxyacetylpyridines and Hydroxy-acetylpiperidines and their Ethylene Ketals. Synthesis and Chemical Behavior.

4:10                 98.  James F. Wolfe and Tommie G. Rogers. Heterocyclic Dianions. Formation and Alkylation of the Glutarimide Dianion.

4:30                 99.  Michael D. Coburn. Synthesis of some Picrylamino- and Nitro-substituted Furazans.

4:50                 100.  U. P. Basu and Bhabatosh Bhattacharya. Hydrogenolysis by Hydrogen-Transfer: Role of Palladium-Charcoal on Halogenated Benzo-Pyridine System.

 

SECTION C: Presiding, H. Smith Broadbent                                                               Education 104

1:30                 101.  G. Grethe, M. Uskokovic, and A. Brossi. Total Synthesis of the Quaternary Benzylisoquinoline Alkaloid Petaline.

1:50                 102.  John L. Neumeyer, Monica McCarthy, and Klaus K. Weinhardt. Fragmentation Products from Borohydride Reductions of Substituted Isoquinolines.

2:10                 103.  Robert N. Schut. The Reaction of 2,3,4,6,7,12-Hexahydroindolo[2,3-a] quinolizine with Electrophilic Olefins.

2:30                 104.  Andre Rosowsky, EIizabeth P. Burrows, Sisir K. Sengupta, and Edward J. Modest. Synthesis and Dehydrogenation of 1,3-Diamino-5,6-Dihydro-benzo[f]quinazoline.

2:50                 105.  C. K. Bradsher and John A. Stone. Stereochemistry of the Addition of Dienophiles to the Acridizinium System.

3:10                 INTERMISSION

3:30                 106.  R. C. Harris. 5,12-Dialkylquinoxalino[2,3-b]phenazines and 12-Alkyl-quinoxalino[2,3-b]phenoxazines.

3:50                 107.  H. Smith Broadbent, Richard C. Anderson, Marvin C. J. Kuchar and Paul D. Ziemer. Preparation and Properties of some Amino- and Thio-Substituted Quinazolines and Quinazoline Oxides.

4:10                 108.  H. Smith Broadbent, James D. Westover Wm. E. Maycock, Kitchener B. Young, and Danny E. Elder. Hydrogenation of Benzodiazines.

4:30                 109.  I. W. Elliott. New Synthetic Approaches to some Isoquinoline Alkaloids: Tetrahydropapaverine and Ophiocarpine.

4:50                 110.  G. W. H. Cheeseman, P. Roy and B. Tuck. Pyrrolo[1,2-a]quinoxalines.

 

SECTION D: Presiding, B. Roth                                                                                 Education 105

1:30                 111.  H. Blatter and Halina Lukaszewski. A New Stable Free Radical.

1:50                 112.  K. D. Berlin, R. Ranganathan, H. Haberlein, and C. Griffin. Phosphorylated Triazoles.

2:10                 113.  H. C. van der Plas and H. Jongejan. Ring Transformations in Reactions of Pyrimidine and its Derivatives with Nucleophiles.

2:30                 114.  E. Babad, Z. Bernstein, and D. Ben-Ishai. Acylation of Substituted Benzimidazoles under Conditions of the Schotten-Baumann Reaction (on the Bamberger Reaction).

2:50                 115.  Tadashi Sasaki and Katsumaro Minamoto. as-Triazine Chemistry. V. The Oxydative Conversion of as-Triazines into 5-Membered Heterocycles.

3:10                 INTERMISSION

3:30                 116.  Barbara Roth. Sulfur EIimination Reactions of Phenacylthiopyrimidines and Related Compounds.

3:50                 117.  K. Freter. Alkylation of Indoles in Aqueous Solution.

4:10                 118.  Albert W. Lutz. Novel Halogenated Imidazoles. Chloroimidazoles.

4:30                 119.  I. Nabih and E. Helmy. Oxidation of N-Methylated Pyrrole, Indole, and Carbazole with Peroxybenzoic Acid.

4:50                 120.  V. P. Mamaev. The Synthesis and Properties of some 2-Substituted Pyrimidines.