The Pyridazines, Volume 57, Supplement 1

by Brown, Desmond J.; Ellman, Jonathan A.; Taylor, Edward C.

• ISBN13: 9780471251378
• ISBN10: 0471251372
• Edition: 1st
• Format: Hardcover
• Copyright: 2000-01-03
• Publisher: Wiley-Interscience

Summary

This new volume substantially updates the original pyridazines volume which was published in 1973. Announcing the latest volume in the successful and prominent Chemistry of Heterocyclic Compounds Series.

Author Biography

Desmond J. Brown is Professor of Chemistry at The Australian National University's Research School of Chemistry.

Table of Contents

Primary Syntheses from Aliphatic or Carbocyclic Synthons	1	(58)
From a Single Six-Atom Synthon	1	(15)
By Completion of the N1--N2 Bond	1	(1)
By Completion of the N2--N3 Bond	2	(1)
From Hydrazonoalkenes or Related Synthons	2	(2)
From (Hydrazonomethyl)cycloalkanes or Related Synthons	4	(1)
From Hydrazonealkanols or Related Synthons	4	(1)
From Hydrazonoalkanals or Related Synthons	5	(1)
From Hydrazonoalkanones or Related Synthons	6	(1)
From Hydrazonoalkanoic Acids or Related Synthons	7	(2)
From Hydrazonolkanoic Esters or Related Synthons	9	(1)
From Hydrazonalkanamides or Related Synthons	10	(1)
From Hydrazonoalkanenitriles or Related Synthons	11	(2)
Completion of the C3--C4 Bond	13	(2)
Completion of the C4--C5 Bond	15	(1)
From Two Synthons	16	(34)
By Using One-and Five-Atom Synthons	17	(1)
By Using Two-and Four-Atom Synthons	18	(1)
Where the Two-Atom Synthon Provides N1 + N2	18	(1)
Using Hydrazine as the N1--N2 Synthon	18	(9)
Using Substituted Hydrazines as N1--N2 Synthons	27	(5)
Using Dialkyl Azodicarboxylates as N1--N2 Synthons	32	(2)
Using Miscellaneous N1--N2 Synthons	34	(2)
Where the Two-Atom Synthon Provides N2 + N3	36	(1)
Where the Two-Atom Synthon Provides C3 + C4	36	(1)
Using Ethylene Derivatives as C3--C4 Synthons	36	(4)
Using Acetylene Derivatives as C3--C4 Synthons	40	(1)
Using Aliphatic Aldehydes or Ketones as C3--C4 Synthons	41	(1)
Using Aliphatic Acids or Acyl Chlorides as C3--C4 Synthons	41	(1)
Using Aliphatic Esters as C3--C4 Synthons	42	(2)
Using Aliphatic Amides or Nitriles as C3--C4 Synthons	44	(1)
Where the Two-Atom Synthon Provides C4 + C5	45	(1)
By Using Two 3-Atom Synthons
Where the Synthons Provide N1 + N2 + C3 and C4 + C5 + C6	46	(3)
Where the Synthons Provide N2 + C3 + C4 and C5 + C6 + N1	49	(1)
From Three or More Synthons	50	(1)
Where Three Synthons Provide N1 + N2, C3 + C4, and C5 + C6	50	(1)
Where Three Synthons Provide N1 + N2 + N3, C4, and C5 + C6	51	(1)
Appendix: Glance Index to Typical Pyridazines Available from Aliphatic or Carbocyclic Synthons	51	(8)
Primary Syntheses from Other Heterocyclic Systems	59	(72)
Pyridazines from Three-, Four-, or Five-Membered Heterocyclic Systems	59	(12)
Azirines as Substrates	59	(1)
Furans as Substrates	59	(5)
Imidazoles as Substrates	64	(1)
Isoxazoles as Substrates	65	(1)
Oxazoles as Substrates	66	(1)
Oxetes as Substrates	67	(1)
Oxirenes as Substrates	67	(1)
Pyrazoles as Substrates	67	(1)
Pyrroles as Substrates	68	(1)
Thiophenes as Substrates	69	(2)
1,2,4-Triazoles as Substrates	71	(1)
Pyridazines from Other Six-Membered Heterocyclic Systems	71	(12)
1,2-Dioxins or 1,2-Dithiins as Substrates	71	(1)
1,3-Dioxins as Substrates	71	(1)
1,3,4-Oxadiazines as Substrates	72	(1)
Pyrans as Substrates	73	(1)
Pyridines as Substrates	74	(1)
Pyrimidines as Substrates	75	(1)
1,2,4,5-Tetrazines as Substrates	75	(6)
1,3,4-Thiadiazines as Substrates	81	(1)
1,2-Thiazines as Substrates	82	(1)
1,2,3-Triazines as Substrates	82	(1)
1,2,4-Triazines as Substrates	83	(1)
Pyridazines from Seven-Membered Heteromonocyclic Systems	83	(4)
1,2-Diazepines as Substrates	84	(1)
1,4,5-Selena-or 1,4,5-Thiadiazepines as Substrates	85	(1)
Thiepines as Substrates	86	(1)
1,2,5-Triazepines as Substrates	86	(1)
Pyridazines from Heterobicyclic Systems	87	(27)
1,2-Benzisoxazoles as Substrates	87	(1)
Benzofurans as Substrates	87	(1)
Cycloocta[d]pyridazines as Substrates	87	(1)
1,2-Diazabicyclo[3.2.0]heptanes as Substrates	88	(1)
3,4-Diazabicyclo[4.1.0]heptanes as Substrates	89	(1)
1,2-Diazabicyclo[3.1.0]hexanes as Substrates	90	(1)
1,6-Diazabicyclo[3.1.0]hexanes as Substrates	91	(1)
2,3-Diazabicyclo[3.1.0]hexanes as Substrates	91	(1)
1,3-Dioxolo[4,5-d]pyridazines as Substrates	92	(1)
Furo[3,2-b]furans as Substrates	93	(1)
Furo[2,3-d]pyridazines as Substrates	93	(1)
Furo[3,2-c]pyridazines as Substrates	94	(1)
Furo[3,4-d]pyridazines as Substrates	94	(1)
Imidazo[1,2-b]pyridazines as Substrates	95	(1)
Imidazo[1,5-b]pyridazines as Substrates	96	(1)
Imidazo[4,5-d]pyridazines as Substrates	96	(1)
Isoxazolo[3,4-d]pyridazines as Substrates	97	(2)
Isoxazolo[4,5-d]pyridazines as Substrates	99	(1)
7-Oxa-3,4-diazabicyclo[4.1.0]heptanes as Substrates	99	(1)
[1,2,4]Oxadiazolo[2,3-b]pyridazines as Substrates	99	(1)
1,2,4-Oxadiazolo[4,5-b]pyridazines Substrates	100	(1)
[1,2,5]Oxadiazolo[3,4-d]pyridazines as Substrates	101	(1)
Oxazolo[4,5-d]-and Oxazolo[5,4-c]pyridazines as Substrates	101	(1)
Oxazolo[3,2-b]pyridazin-4-iums as Substrates	102	(1)
Phthalazines as Substrates	103	(1)
Pyrano[2,3-d]pyridazines as Substrates	103	(1)
Pyrazino[2,3-d]pyridazines as Substrates	104	(1)
Pyrazolo[1,2-a]pyridazines as Substrates	104	(1)
Pyrazolo[3,4-d]pyridazines as Substrates	105	(1)
Pyridazino[3,4-d][1,3]oxazines as Substrates	105	(1)
Pyridazino[4,5-d][1,3]oxazines as Substrates	106	(1)
Pyridazino[1,2-a]pyridazines as Substrates	106	(1)
Pyridazino[4,5-d]pyridazines as Substrates	107	(1)
Pyridazino[1,6-a]1,3,5-and Pyridazino[6.1-c][1,2,4] triazines as Substrates	107	(1)
Pyrido[1,2-b]pyridazin-9-iums as Substrates	108	(1)
Pyrimido[4,5-c]pyridazines as Substrates	108	(1)
Pyrimido[4,5-d]pyridazines as Substrates	109	(1)
Pyrrolo[3,2-c]pyridazines as Substrates	109	(1)
Quinolines as Substrates	109	(1)
[1,2,4]Thiadiazolo[2,3-b]pyridazines as Substrates	110	(1)
[1,3,4]Thiadiazolo[3,4-a]pyridazines as Substrates	111	(1)
Thiazolo[3,2-b]pyridazin-4-iums as Substrates	111	(1)
Thieno[2,3-c]pyridazines as Substrates	111	(1)
Thieno[3,4-d]pyridazines as Substrates	112	(1)
3,4,7-Triazabicyclo[4.1.0]heptanes as Substrates	112	(1)
[1,2,4]Triazolo[1,2-a]pyridazines as Substrates	113	(1)
Pyridazines from Heterotricyclic Systems	114	(4)
Pyridazines from Heterotetracyclic Systems	118	(1)
Pyridazines from Bridged Heterocyclic Systems	119	(3)
Pyridazines from Spiro Heterocyclic Systems	122	(2)
Appendix: Glance Index to Typical Pyridazines Readily Available from Other Heterocyclic Systems	124	(7)
Pyridazine, Alkylpyridazines, and Arylpyridazines	131	(46)
Pyridazine	131	(9)
Preparation of Pyridazine	131	(1)
Physical Aspects of Pyridazine	132	(2)
Reactions of Pyridazine	134	(6)
C-Alkyl-and C-Arylpyridazines	140	(31)
Preparation of C-Alkyl-and C-Arylpyridazines	140	(1)
By Direct Alkylation	140	(4)
By Nuclear Addition Reactions	144	(3)
By Displacement Reactions	147	(5)
By Elimination of Functional Groups	152	(3)
By Modification of Aldehydes, Ketones, or Esters	155	(2)
By Interconversion of Simple Alkyl Substituents	157	(2)
Properties and Reactions of C-Alkyl-and C-Arylpyridazines	159	(1)
Oxidative Reactions	160	(3)
Extranuclear Alkylation and Alkylidenation	163	(3)
Extranuclear Acylation	166	(1)
Extranuclear Halogenation, Nitration, and Diazo Coupling	167	(1)
Miscellaneous Reactions	168	(3)
N-Alkylpyridazinium Salts and Related Ylides	171	(6)
Preparation of N-Alkylpyridazinium Salts	171	(1)
Preparation of Pyridazinium Ylides	172	(1)
Reactions of N-Alkylpyridazinium Salts	173	(2)
Reactions of Pyridazinium Ylides	175	(2)
Halogenopyridazines	177	(74)
Preparation of Nuclear Halogenopyridazines	177	(16)
Nuclear Halogenopyridazines from Pyridazinones	177	(1)
Using Neat Phosphoryl Chloride	177	(5)
Using Phosphoryl Chloride in a Solvent	182	(1)
Using Phosphorus Pentachloride in Phosphoryl Chloride	182	(2)
Using Phosphoryl Chloride and a Tertiary Base	184	(1)
Using Phosphoryl Bromide or Phosphorus Pentabromide	185	(1)
Using Other Reagents	185	(2)
Nuclear Halogenopyridazines by Direct Halogenation	187	(1)
Nuclear Halogenopyridazines from Metallopyridazines	188	(1)
Nuclear Halogenopyridazines from Nitropyridazines	189	(1)
Nuclear Halogenopyridazines by Transhalogenation	190	(2)
Nuclear Halogenopyridazines from Pyridazinamines	192	(1)
Reactions of Nuclear Halogenopyridazines	193	(44)
Aminolysis of Nuclear Halogenopyridazines	193	(1)
3/6-Monohalogenopyridazines as Substrates	193	(6)
4/5-Monohalogenopyridazines as Substrates	199	(3)
3,4/5,6-Dihalogenopyridazines as Substrates	202	(1)
3,5/4,6-Dihalogenopyridazines as Substrates	203	(1)
3,6-Dihalogenopyridazines as Substrates	203	(5)
4,5-Dihalogenopyridazines as Substrates	208	(1)
3,4,5/4,5,6-Trihalogenopyridazines as Substrates	209	(3)
3,4,5,6-Tetrahalogenopyridazines as Substrates	212	(1)
Hydrolysis of Nuclear Halogenopyridazines	213	(3)
Alcoholysis of Nuclear Halogenopyridazines	216	(5)
Thiolysis of Nuclear Halogenopyridazines	221	(2)
Alkanethiolysis of Nuclear Halogenopyridazines	223	(5)
Conversion of Nuclear Halogeno-into Azidopyridazines	228	(3)
Hydrogenolysis of Nuclear Halogenopyridazines	231	(3)
Other Displacement Reactions of Nuclear Halogenopyridazines	234	(1)
Reactions Involving Ring Fission of Nuclear Halogenopyridazines	235	(2)
Preparation of Extranuclear Halogenopyridazines	237	(5)
Extranuclear Halogenopyridazines from the Corresponding Hydroxypyridazines	237	(3)
Extranuclear Halogenopyridazines by Halogenation	240	(1)
Extranuclear Halogenopyridazines by Passenger Halogenation	241	(1)
Reactions of Extranuclear Halogenopyridazines	242	(9)
Aminolysis of Extranuclear Halogenopyridazines	242	(1)
Alcoholysis of Extranuclear Halogenopyridazines	243	(1)
Thiolysis of Extranuclear Halogenopyridazines	244	(1)
Alkanethiolysis of Extranuclear Halogenopyridazines	245	(1)
Hydrogenolysis of Extranuclear Halogenopyridazines	246	(1)
Other Displacement Reactions of Extranuclear Halogenopyridazines	246	(5)
Oxypyridazines	251	(72)
Tautomeric Pyridazinones	252	(21)
Preparation of Tautomeric Pyridazinones	252	(5)
Reactions of Tautomeric Pyridazinones	257	(1)
Conversion into Pyridazinethiones	257	(2)
Conversion into O-or N-Alkyl Derivatives	259	(8)
Conversion into O-or N-Acyl Derivatives	267	(2)
Reductive Reactions	269	(1)
Miscellaneous Reactions	270	(3)
Pyridazine Quinones	273	(3)
Extranuclear Hydroxypyridazines	276	(7)
Preparation of Extranuclear Hydroxypyridazines	276	(4)
Reactions of Extranuclear Hydroxypyridazines	280	(3)
Nuclear and Extranuclear Alkoxy-and Aryloxypyridazines	283	(9)
Preparation of Alkoxy-and Aryloxypyridazines	283	(4)
Reactions of Alkoxy-and Aryloxypyridazines	287	(1)
Aminolysis and Related Processes	287	(1)
Thermal Rearrangement	288	(1)
Hilbert-Johnson Reaction	289	(1)
Other Reactions, Including Those of Epoxides	290	(2)
Nontautomeric Pyridazinones and N-Alkylpyridaziniumolates	292	(10)
Preparation of Nontautomeric Pyridazinones	292	(3)
Reactions of Nontautomeric Pyridazinones	295	(7)
Pyridazine N-Oxides	302	(9)
Preparation of Pyridazine N-Oxides	302	(2)
Reactions of Pyridazine N-Oxides	304	(7)
Ancillary Aspects of Oxypyridazines	311	(12)
X-Ray Structural Analyses of Oxypyridazines	312	(2)
Studies of Fine Structure in Oxypyridazines	314	(1)
General Spectral and Related Studies on Oxypyridazines	315	(2)
Trivial Names for Pyridazine Derivatives	317	(6)
Thiopyridazines	323	(20)
Pyridazinethiones and Pyridazinethiols	323	(11)
Preparation of Pyridazinethiones and Pyridazinethiols	323	(2)
Reactions of Pyridazinethiones and Pyridazinethiols	325	(1)
S-Acylation	326	(1)
S-Alkylation	326	(5)
N-Alkylation	331	(1)
Aminolysis	331	(1)
Oxidation to Dipyridazinyl Disulfides	332	(1)
Other Reactions	333	(1)
Alkylthiopyridazines and Dipyridazinyl Sulfides	334	(5)
Preparation of Alkylthiopyridazines	334	(1)
Reactions of Alkylthiopyridazines	335	(1)
Oxidation to Sulfoxides or Sulfones	335	(1)
Miscellaneous Minor Reactions	336	(3)
Dipyridazinyl Disulfides and Pyridazinesulfonic Acids or Related Compounds	339	(1)
Pyridazine Sulfoxides and Sulfones	340	(3)
Nitro-, Amino-, and Related Pyridazines	343	(44)
Nitropyridazines	343	(5)
Preparation of Nitropyridazines	343	(1)
Reactions of Nitropyridazines	344	(1)
Reduction	344	(3)
Displacement Reactions	347	(1)
Regular Aminopyridazines	348	(23)
Preparation of Regular Aminopyridazines	348	(7)
Reactions of Regular Aminopyridazines	355	(1)
N-Acylation and Subsequent Reactions	356	(3)
N-Alkylidenation and Subsequent Reactions	359	(1)
N-Alkylation Reactions	360	(3)
Conversion into Ureidopyridazines or Related Products	363	(3)
Miscellaneous Reactions	366	(3)
Ancillary Information	369	(2)
Hydrazino-, Hydroxyamino-, and Azidopyridazines	371	(13)
Preparation of Hydrazinopyridazines	371	(2)
Reactions of Hydrazinopyridazines	373	(7)
Preparation and Reactions of Hydroxyaminopyridazines	380	(1)
Preparation, Isomerization, and Reactions of Azidopyridazines	381	(3)
Preparation and Reactions of Nontautomeric Pyridazinimines	384	(2)
Preparation and Reactions of Arylazopyridazines	386	(1)
Pyridazinecarboxylic Acids and Related Derivatives	387	(48)
Pyridazinecarboxylic acids	387	(10)
Preparation of Pyridazinecarboxylic Acids	387	(5)
Reactions of Pyridazinecarboxylic Acids	392	(5)
Pyridazinecarboxylic Esters	397	(10)
Preparation of Pyridazinecarboxylic Esters	397	(4)
Reactions of Pyridazinecarboxylic Esters	401	(6)
Preparation and Reactions of Pyridazinecarbonyl Halides	407	(2)
Preparation and Reactions of Pyridazinecarboxamides	409	(4)
Preparation and Reactions of Pyridazinecarbohydrazides.	413	(2)
Preparation and Reactions of Azidocarbonylpyridazines	415	(1)
Pyridazinecarbonitriles	416	(8)
Preparation of Pyridazinecarbonitriles	417	(3)
Reactions of Pyridazinecarbonitriles	420	(4)
Pyridazinecarbaldehydes	424	(5)
Preparation of Pyridazinecarbaldehydes	424	(1)
Reactions of Pyridazinecarbaldehydes	425	(4)
Pyridazine Ketones	429	(6)
Preparation of Pyridazine Ketones	429	(1)
Reactions of Pyridazine Ketones	430	(5)
Appendix Table of Simple Pyridazines	435	(134)
References	569	(64)
Index	633