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Advances in Heterocylic Chemestry. Vol 10 - Boulton A.J.

Advances in Heterocylic Chemestry. Vol 10

Author: Boulton A.J.
Publishers: Academic Press
Year of publication: 1969
Number of pages: 347
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Download: advensisheroklinik1969.pdf

Pyridopyrimidines:
I.3.5-) I.3.6-, 1,3.7-. and 1,3,8-Triazanaphthalcnes
W. J. Irwin and D. G. Wibberlky
I. Introduction ......... 149
II. Syntheses . . . . . . . . . .150
III. Physical Properties . . . . . . . .182
IV. Chcmical Properties . . . . . . . .189
Y. Pyridopyrimidines of Biological Interest . . . .197
Cyclic Hydroxamic Acids
J. B. Bapat, D. St. C. Black, and R. F. C. Brown
I. Introduction . . . . . . . . .199
II. Naturally Occurring Compounds ...... 201
III. Synthesis of Cyclic Hydroxamic Acids ..... 205
IV. Characteristic Reactions ....... 226
V. Physical Properties ........ 234
Pyrylium Salts Part I. Syntheses A. T. Balaban, W. Schroth, and G. Fischer
I. Introduction ......... 241
II. Syntheses .......... 249
III. Conclusion .......... 325
Author Index .......... 327
Cumulative List of Titles, Volumes 1-10
346
Benzofuroxans
A. J. BOULTON
School of Chemical Sciences, University of East Anglia,
Norwich, Norfolk, England
AND
P. B. GHOSH
Department of Medical Chemistry, The Australian National University, Canberra, A.C.T., Australia
I. Introduction ......... 2
IT. Structure ’
III. Spectroscopic and Other Physical Properties ... 6
A. Infrared Spectra ....... 6
B. Ultraviolet Spectra ...•••• 7
C. Nuclear Magnetic Resonance Spectra .... 8
D. X-Ray Diffraction.................................11
E. Physical Properties . • - • • • .12
IV. Preparation of Benzofuroxans . . • • • .12
V. Substituted Benzofuroxans: Reactions of Substituents . 15
A. Alkyl and Aryl Benzofuroxans . . • • 15
B. Annellated Benzofuroxans . . . . . .15
C. Heterosubstituted Benzofuroxans . . • .17
D. Amino-and Àñólaminobenzofuroxans . . . .17
E. Hydroxy benzofuroxans and Derivatives . . .18
F. Halobenzofuroxans . . . • ¦ ¦ .19
G. Nitrobenzofuroxans . . . ¦ ¦ • .19
H. Acyl-and Carboxy-Substituted Benzofuroxans . . 19
VI. Reactions of the Heterocyclic Ring ..... 20
A. Electrophilic Attack 20
B. Oxidation ........ 21
C. Reduction ........ 21
D. Miscellaneous Reactions ...... 23
VII. Reactions of the Homocyclic Ring .... 24
A. Electrophilic Attack 24
B. Nucleophilic Attack ....... 25
VIII. Rearrangements ........ 27
IX. Uses .......... 30
X. Table of Benzofuroxans ....... 31
I. Introduction
The bonzofuroxan [benzofurazan oxide,* 3,4-benzo-l,2,6-oxa-diazole-2-oxide, or 2.1,3-benzoxadiazole-1 -oxide (1)] ring system has been reviewed briefly on several occasions, notably by Kaufman and Picard,1 Boyer,2 and Behr.3 The most recent of these3 covers the literature until 1959, and since that date there have been many advances in the subject. This, we feel, justifies the field being covered once more, and its separation from the monocyclic 1,2,5-oxadiazole oxides—the furoxans. We consider also other furoxano-fused compounds in this chapter, subject to the limitation that the ring adjacent to the furoxan is aromatic and six-membered..
The benzo-annellated derivative naphtho[l,2-c]furoxan is numbered according to the system (2)] shown. In the literature the name
1,2-naphthofuroxan may often be found, with the same numbering as for a 1,2-disubstituted naphthalene. Although the latter method is perhaps a little clearer to follow, the more systematic scheme (2) will be adhered to in this chapter.
Ï. Structure
The literature on benzofuroxans is considerably complicated by uncertainties concerning their structure, which were resolved only in 1960. Thus, Beilstein’s Hauptwerk includes them in Volume 7 (as derivatives of o-quinones, depicted as dioxadiazines, and named as
* Chemical Abstracts preferred name, which seems to us to embody the disadvantages of both systematic and trivial nomenclature.
1 J. V. R. Kaufman and J. P. Picard, Chem. Bev. 59, 429 (1959).
2 J. H. Boyer, in “Heterocyclic Compounds” (R. Ñ. Elderfield, ed.), Vol. 7, pp. 462-508, 1961.
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