By Dr. D. J. Brown(auth.), Edward C. Taylor, Peter Wipf, Arnold Weissberger(eds.)
This booklet presents the main finished, present reference at the man made chemistry of cinnolines and phthalazines. functions to the syntheses of common items and different chiral compounds are defined. quantity sixty four comprises chapters exploring the next topics:
* basic Syntheses of Cinnolines
* Cinnoline, Alklycinnolines, and Arylcinnolines
* Nitro-, Amino-, and similar Cinnolines
* Cinnolinecarboxylic Acids and comparable Derivatives
* fundamental Syntheses of Phthalazines
* Phthalazine, Alklyphthalazines, and Arylphthalazines
* Phthalazinecarboxylic Acids and similar Derivatives
* An Appendix of Tables of straightforward Cinnolines and easy PhthalazinesContent:
Chapter 1 basic Syntheses of Cinnolines (pages 1–32):
Chapter 2 Cinnoline, Alkylcinnolines, and Arylcinnolines (H four, 6, forty six; E 1, 18, three hundred) (pages 33–44):
Chapter three Halogenocinnolines (H 29; E 121) (pages 45–58):
Chapter four Oxycinnolines (H sixteen, 29, forty eight; E sixty two, a hundred and fifty, 273) (pages 59–77):
Chapter five Thiocinnolines (E a hundred and seventy) (pages 79–83):
Chapter 6 Nitro?, Amino?, and comparable Cinnolines (H 35; E 87, 207) (pages 85–94):
Chapter 7 Cinnolinecarboxylic Acids and similar Derivatives (H eleven; E 250) (pages 95–108):
Chapter eight fundamental Syntheses of Phthalazines (pages 109–171):
Chapter nine Phthalazine, Alkylphthalazines, and Arylphthalazines (H sixty nine, seventy two; E 324, 338) (pages 173–202):
Chapter 10 Halogenophthalazines (H 178; E 514) (pages 203–234):
Chapter eleven Oxyphthalazines (H seventy eight, 177; E 364, 375, 445) (pages 235–280):
Chapter 12 Thiophthalazines (E 535) (pages 281–290):
Chapter thirteen Nitro?, Amino?, and comparable Phthalazines (H 183; E 560,596) (pages 291–318):
Chapter 14 Phthalazinecarboxylic Acids and comparable Derivatives (E 638) (pages 319–347):
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Additional resources for Cinnolines and Phthalazines: Supplement II, Volume 64
441 R O N NH (42) From Acylcinnolines Note: N-Acylated hydrocinnolines have been reduced to the corresponding N-alkylhydrocinnolines. 962,964 OCH2Ph OCH2Ph LiAlH4 N N CH2CH(CH2)2 OCCH2Ph (43) N N CH2CH(CH2)2 CH2CH2Ph (43a) Alkyl- and Arylcinnolines 41 From Other Alkylcinnolines Note: Modification of existing alkyl may be done in a number of ways; some are exemplified here. 636,959 CH CHNHPh N N+ I− Me (48) PhN CH3 CHNHPh (R = Me) N N+ I− R p-Me2NC6h4CHO (R = Et) (49) CH CHC6H4NMe2-p N N+ I− Et (50) By Quaternization Note: This process is often used but seldom described.
4. FROM OTHER HETEROMONOCYCLIC SUBSTRATES The formation of cinnolines from heteromonocyclic systems other than pyridazine is rare. However, at least three such systems have been so used, as illustrated in the following examples. 5. FROM HETEROBICYCLIC SUBSTRATES Several heterobicyclic systems have been used to make cinnolines, but only one has been so employed to any extent. The following examples illustrate the variety of reactions involved. 213 O O CH2CH2CO2H HONO N H N H O (168) N (169) Benzofuran Derivatives as Substrates 2-Acetoxy-2-methyl-2,3,4,5,6,7-hexahydrobenzofuran-3-one (170) with hydrazine gave 3-methyl-5,6,7,8-tetrahydro-4(1H)-cinnolinone (171) (EtOH, 20 C, 12 h: 85%) or with methylhydrazine gave a separable mixture of 1,3dimethyl-5,6,7,8-tetrahydro-4(1H)-cinnolinone (172) and 2,3-dimethyl-5,6, 7,8-tetrahydrocinnolin-2-ium-4-olate (173) (EtOH, 0 C !
In using the index, it should be borne in mind that products broadly analogous to those formulated may often be obtained by minor changes to the substrates and/or synthons involved. 6 N NH NH NH2 CH2CO2Et Me Me N N CHAPTER 2 Cinnoline, Alkylcinnolines, and Arylcinnolines (H 4, 6, 46; E 1, 18, 300) This chapter covers information (reported during the period 1972–2004) on the preparation, physical properties, and reactions of cinnoline and its C-alkyl, C-aryl, N-alkyl, and N-aryl as well as their respective nucleus-reduced analogs.
Cinnolines and Phthalazines: Supplement II, Volume 64 by Dr. D. J. Brown(auth.), Edward C. Taylor, Peter Wipf, Arnold Weissberger(eds.)