FIRST INTERNATIONAL CONGRESS OF HETEROCYCLIC CHEMISTRY
THE UNIVERSITY OF NEW MEXICO,
ALBUQUERQUE, NEW MEXICO
JUNE 12-15, 1967
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General Chairman
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Raymond N. Castle
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Advisory Committee
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Editorial Board of the Journal of
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Heterocyclic Chemistry
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P R O G R A M
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Welcome and Introductory
Remarks
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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,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.