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Additional info for Science of Synthesis: Six-membered Hetarenes with Two Identical Heteroatoms v. 16 (Houben-Weyl Methods of Organic Chemistry)

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A similar reaction pattern is seen for 3-halocinnolines 109. 9 Cinnolines Scheme 41 Reaction of 4-Chloro- and 8-Iodocinnolines with Arylboronic Acids (Suzuki Reaction)[104] Ar1 Cl Ar1B(OH)2, Pd(PPh3)4 aq K2CO3, DME N 1. LDA, TMSCl 2. 1 mmol), 2 M aq K2CO3 (2 ml, 4 mmol), and EtOH (1 mL) in degassed DME (15 mL) was refluxed for 16 h under a N2 atmosphere. The mixture was cooled and diluted with H2O/CH2Cl2 (15 mL), and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (3 ” 15 mL) and the combined organic extracts were dried (MgSO4) and evaporated.

2 mmol) and 90% H2NNH2 (2 mL, 57 mmol) in EtOH (50 mL) were left at rt for 4 d. 77 g (91%); mp 293–294 8C (dec, substance turned deep red at 200–210 8C). The use of 50% H2NNH2•H2O led to a slightly lower yield (81%). 11 mmol) was added to stirred molten NH4OAc (5 g, 65 mmol) at 137 8C and kept at this temperature for 30 min. The clear orange soln was cooled, treated with 10% aq NaOH (100 mL), and set aside for 4 d. The pure diamine separated as long, very pale yellow needles; yield: 230 mg (68%); mp 250 8C (dec), unchanged by recrystallization (H2O).

147,178] The best results are obtained with iodo-substituted reactants, with no reaction occuring for 3-chlorocinnolines. A similar reaction pattern is seen for 3-halocinnolines 109. 9 Cinnolines Scheme 41 Reaction of 4-Chloro- and 8-Iodocinnolines with Arylboronic Acids (Suzuki Reaction)[104] Ar1 Cl Ar1B(OH)2, Pd(PPh3)4 aq K2CO3, DME N 1. LDA, TMSCl 2. 1 mmol), 2 M aq K2CO3 (2 ml, 4 mmol), and EtOH (1 mL) in degassed DME (15 mL) was refluxed for 16 h under a N2 atmosphere. The mixture was cooled and diluted with H2O/CH2Cl2 (15 mL), and the organic layer was separated.

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