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16.10 Product Class 10: Phthalazines

DOI: 10.1055/sos-SD-016-00385

Haider, N.; Holzer, W.Science of Synthesis, (200416315.

General Introduction

Phthalazine (1) is a benzo-fused pyridazine, namely benzo[d]pyridazine. Especially in older literature, 1 is occasionally called 2,3-benzodiazine, 2,3-diazanaphthalene, β-phenodiazine, or 2,3-naphthyridine. Because of the high single-bond character of the NN bond in 1, which is well-confirmed both theoretically and experimentally, phthalazine is exclusively represented as the Kekulé structure (Scheme 1).

Meeeee 8 Meeeeeeee ee eee Meeeeeeeeee Meeeeeee

Mee eeeeeeeee eee eeeeeeee, eeeeeeeeeeeee, eee eeeeeeeeee eeeeeeeeee ee eeeeeeeeeeee eeee eeee eeeeeeee eeeeeeeeeee;[‌8‌‌8‌] eeeeeeeee eeeeeeeeeee ee eeee eeeeeeee ee MeeeeeMeee, Mee.M 8e, ee888888. Mee eeeee eeeeeeeeeee ee eee eeeeee eeeeeeee 8 eee eeeeeeeee ee 8888.[‌88‌]

Meeeeeeeeee eeeee eeeeeeeee eeeeee eeee eee eeeeeee ee eeeee eee ee eeee eeeeeee eeeeeeee eeeeee eeeeeee (eeeeeeeee eeeeeee). Me ee e eeeeeeee eeeeeeee eeee eeee eeeeeeeeee ee eeeeeeeee, eee eeeee eeeeee eeeee eeee ee eee eeeeeeeeeeeeeeeee (ee 888°M;[‌88‌] 888888°M[‌88‌]), eeeeeeeeeeeeeeee (ee 888888°M[‌88‌]), eeeeeeeeeeeeeee (ee 888°M[‌88‌]), eee eee eeeeeee (ee 888888°M[‌88‌]). Meee eeeeeeee eeeeeeeeee ee eeeeeeeeeee eee eeeeeeeeee eeeee; eee eeeeee eeeeeeeeee[‌8‌‌8‌] eeeeeeee eeee eeeeeeee eeeeeeeeeee.

Meeeeeeeeee: ee ee eeee eeee: 8888°M;[‌88‌] 88.888°M eeeee eeeeeeeeeee ee 888°M/8.8Meee;[‌88‌] ee: 888888°M/888Meee (eeee eeeeeeeeeeeee);[‌88‌] 888°M/88Meee;[‌88‌] eMe ee M8M ee 88°M: 8.88;[‌88‌] eeeeee eeeeee: 8.88M;[‌88‌] eeeeeeeeee eeeeeeeee: 8.88eM.[‌88‌]

Meeeeeeeeeeee eeeeeeeeeeee ee eeeeeeeeeee eeee eee eeeeeeeee eee (MM8+) eeeee eeeeee eee 8-eeeeeeeeeee eeeeeee.[‌88‌] Meeeeeeee ee 8 eeee eeeeeee eeeeeeee eeeeeee eeeeeeee 8,8-eeeeeeeeeeeeeeeeee;[‌88‌] eee 8,8,8,8-eeeeeeeeee eeeeeeeeee ee eeeeeeee eeee eeeeeeeee eeee eeeeee eeeeeee.[‌88‌,‌88‌] Meeeeeee eeee eeee eee eeeeeeeeeeee eeee eeeee ee eeee eeeeeee, eeeeee 8-(eeeeeeeeeee)eeeeeeeeeee,[‌88‌] eeeee ee eeee eeeeeeee eeee eeeeeeeee eeeeeeeee.[‌88‌] Mee eeeeeeeeeee eeeeeee ee eeeeeee eeeeeeee ee eeeeeeeeeee 8-eeeee eeee eeeeeeee eeee eeeeeeeeeeeeeeeeee eeee.[‌88‌] Meeeeeeee ee eeeeeeeeeee eeee eee eeeeee eeeeeee eeeeeeeee eeeeeeeeeeee ee eeeeeeee eeeeee eeeee ee eeeeeeee ee eee eeeeeee eeee, eeeeeeeee ee eee eeeeeeeee ee eeeeeeeeee-8,8-eeeeeeeeeeee eeee.[‌88‌]

Meeeeeeeeeeee MMM (eeee-eeeeeeeeee eeeee) eeeeeeee eeeeee eee MMM (eeeeeeee Müeeee eeeeee), MMMM (eeeeeeee eeeeeee ee eeeeeeeeeeee eeeeeee), ee MMMM (eeeeeeeeeeee eeeeeee ee eeeeeeeeeeee eeeeeee) eeeeeeeeeeeee eeee eeee eeee ee eeeeeeeee eeeeeeeee eeeeeeeeee,[‌88‌] eeeeeeee eeeeeeeee,[‌88‌‌88‌] eee eeeee eeeeeeeeeeeeeee eeeeeeeeee eeee ee eeeeee eeeeee,[‌88‌] eeeeeeeeee eeeeeeeee,[‌88‌] 88M eeeeeeee eeeeee,[‌88‌] eee eeeeeeee eeeeeeee eeeeeeeee[‌88‌] ee eeeeeeeeeee. Meee eeeeeeee, ee eeeeee eeeeeee ee eee MM/888M* eee MMM/888M eeeeee (MMM=eeeeeeeeeeeee eeeeeeeeeee eeeeeee) eeee eeee eeee eeeeeeee ee eeeeeee eee eeeeeeeeeee eeeeeeeeeee ee eeeeeeeeeee eee eeeeeeeeeee-e8 eee eee eeeeee eee eeeeeee eeeeeeeeee eeeeee, eeeeeeeeeeee.[‌88‌] Meeeeeee, eee eeeee eeeeeeeeee eeeeeeee eee eeeeeeee eeeee ee eeeeee, eeeeeeeeeeeee, eee eeeeeeeeee eeeeeee eeeeeeeeeeee.[‌88‌] Me eeeeee MMM MM eeeeeeeeeeee eeee eeee eeee ee eeeeeeeee eee eeeeeeee eeeeeeeeee ee eeeeeeeeeee eee eeeee eeeeee eee eeeeeeee[‌88‌] eee ee eeeeeeeee M eeeeeeee eeeee eeeeeeeee,[‌88‌] eeeeee eeeeeeeeeeeee,[‌88‌] eee eeee eeeeeeeee.[‌88‌] Meeeeeeeeeee eeeeeee eeeeeeeeeeeeee eeeeeeeeee MMM eeeeeeee eeeeee (88M, 88M, 8M) eee MMMM/MMM eeeeeeeeee eeeeeeeee eeeeeeeee eeeeeeeee eeee eeeeeeeeee eeee e eeeeee ee M-eeeeeeeeee eeeeeeeeeeee, eeeeeeeee eeeeeeeeeee.[‌88‌]

Mee eeeeeeeeeee ee eeeeeeeeeeeeee eee eeee eee eeeeeee ee eeeeeeee eeeeeee. Meeeeeeeee-8(8M)-eee (8) eee eeeee eeeeee ee eee eee (8M) ee ee eee eeeeeee eeee (8M) (Meeeee 8). Meeee ee MM[‌88‌,‌88‌] eee MM eeeeeee,[‌88‌‌88‌] eee eeeee eeeeeeeeeeee ee eee eee eeee ee eeeeeeee eee eeee eeeee. Mee 8-eeeeeeeeeeeeeeeee-8(8M)-eee (8), eee eeeeeeeeeeeeeeeeeeee eeeeeeeee (8M) ee eeeeeeeee (Meeeee 8).[‌88‌] Meee eee ee eeeeeeeeee ee eee eeeeeeeee ee eeee 8M eee 8M, eeeeeeeee eeeeeeee eeeeeeee eeeee ee eee eeee eeeeeeeeeeeee eeee.[‌88‌] Mee eeeeeeeeee eeeeeeee ee eeeeeeeeeeeeeeeeee (eeeeeeeeeeeeeeeeeeee) eeeeeee eeeeeeeee eeee ee eee eeeeeeeeeeeee eeeeee eeeeeeeee.[‌88‌]

Meeeee 8 Meeeeeeeeee ee Meeeeeeeeeeeee

Mee 8MMMM eeeeeeee ee eeeeeeeeeee ee eeeeeee-e8 eee eeeeeeee ee eee eeeee ee eeee eeeeeeeeee, eee eeee eeeeeee ee eee eeeeeee eeeeee eeeeee eeee ee ee MMMM eeee eeeeee ee e eeeeeeeeeeee eeeeeeeee ee 88MMe (Meeeee 8).[‌88‌] Mee 88MMMM eeeeeeee ee 8 ee MMMe8 eeeeeeee eeeeeeeeee eeeeeeee eeeeee eee eeeeeee M8e/M8e eee eee M8/M8, eee eee eeeeeeeee eeeeeeee eeeee eeeeeeeeeeee (Meeeee 8).[‌88‌] Mee eM eeeeeeeeee ee eee 88M eeeeeeee eeeeee ee eeeeeee eeeeeeee eee eeee eeeeeee.[‌88‌] Mee 88MMMM eeeeeeee eeeee (eeeeeeeeee eeeeeee eeeeeeee, eeee eeeeeeeeeeee) ee eee eeeeeeeeeee eeeeeeeee ee δ 88.8 ee eeeeeeeeeeeeeeeee[‌88‌] eee δ 8.8 ee eeeeeee,[‌88‌] eeeeeee eeeeeeeeeee 8-eeeee ee eeeeeeeeeeeeeeeee eeeeeeee δ(M8) 88.8 eee δ(M8) 88.8.[‌88‌]

Meeeee 8 8MMMM eee 88MMMM Meee eee Meeeeeeeeee[‌88‌,‌88‌]

Meeeeeee eeeeeeeeee eeee[‌88‌‌88‌] eee Meeee eeeeeee[‌88‌,‌88‌,‌88‌] ee eeeeeeeeeee eeee eeee eeeeeeee. Meeeeeeeeeeeee MM eeeeeeeeee eeeee eee eeeeeeeeeee (MMe eeeeee) eee:[‌88‌] ν̃ (ee8)=8888, 8888, 8888, 8888, 8888, 8888, 888.

Meeeeeee MM eeee eee eeeeeeeeeee eee eeeeeeeee; eeeeeee eeee eeee eeeeeeee, eee eeeeeeee, ee eeeeeeeeeee,[‌88‌,‌88‌] eeeeeeeeeeeeeeeee,[‌88‌] eeeeeee,[‌88‌] eeeeeee,[‌88‌] eeeeeeee,[‌88‌,‌88‌] eee eeeee.[‌88‌,‌88‌] Mee eeeee eeeeeeeeee eeeeeeee ee 8 eee eeee eeeeeeee eee eeeeeeee.[‌88‌] Meeeeeeeeeeeee MM eeeeeeeeee eeeee ee eeeeeeeeeee (ee eeeeeeeeeee) eee:[‌88‌] λeee (ee) (eeee eee εeee ee eeeeeeeeeee)=888 (8.88), 888 (8.88), 888 (8.88), 888 (8.88), 888 (8.88), 888 (8.88), 888 (8.88), 888 (8.88), 888 (8.88), 888 (8.88), 888 (8.88), 888 (8.88), 888 (8.88).

Me eee eeeeeeee-eeeeee eeee eeeeeeee ee eeeeeeeeeee, eee eeeeeee eeeeeeeeeeeee eeeeeee eeeeeeee eee eeeeeeeeee eeee ee eee MMM eeeee eeee eee eeeeeeeee eee (eee eeeeee eeee eeeeeeeeeeee eee eeee eeee), eeeeeeee ee eeee ee eeeeee.[‌88‌,‌88‌,‌88‌] Mee eeeeeeeeeeeeee eeee eeeeeeee eeeeeeeeeeeee eeeeeee ee eeeeeeeeeee (MM, 88eM) ee:[‌88‌] e/e (%)=888 (888, M+), 888 (88, M+ MMM), 888 (88, M+ M8), 88 (88, M+ 8MMM), 88 (88, M+ 8MMM M8M8).

Mee eeeeeeeee ee eeeeeeeeeee eee eeee eeee eeeeeeeeee ee M-eee eeeeeeee;[‌88‌] eeee eeeeeee eee eeeeeeee ee Meeeee 8.

Meeeee 8 Meee Meeeeee (Å) Meeeeeee eeee M-Mee Meeeeeee ee Meeeeeeeeee[‌88‌]

Meeeeeeeee ee eee eeeeee eeeeeeeeee, e eeee eeeeeee ee eeeeeeeeee eeeeeeeeee eeee eeee eeeeeeee eee eeeeeeeeeee eeeeeeeeeee eeeee eeeeee ee eeeeeee ee eeeeee eeee. Meeeeee, ee eeeee eee eeee-eeeee eeee ee eeeeeeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeee eeeee[‌88‌] eee ee ee eeeeeeeee eeeeeeeeee. Meeeee eeeeeeeeeeee eeeee eeeeeeeeeeee eeee eeeeeeeeeeeeee,[‌88‌] eeeeeeeeeeee/eeeeeeeeeeeee,[‌88‌] eeeeeeeeeeeeee/eeeeeeeeeeeee,[‌88‌‌88‌] eeeeeeeee,[‌88‌,‌88‌] eeee-eeeeeeeeeeee,[‌88‌,‌88‌] eeeeeeeeeee eeeeeeeeeeee,[‌88‌] eee eeeeeeeeeeeeee eeeeeeee.[‌88‌] Meeeeeee, eeee eeeeeeeeeee eeeeeeeeeee eeee eeee eeeee ee eee ee eeeeeeeeee ee eeeeeeeeeeeeeeeee MM[‌88‌‌88‌] eee eeeeeeeeeeeeeeeee M,[‌88‌‌88‌] eee eeeeee eeee eeee eeeeeeeee eeeeeee eeeeeeeee eeeeeeeeeeee eee eeeeeeee eeeeeeeeeee. Meeeee 8 eeeee eeeeeeeeeee-eeeeeee eeee eeeeeeeee eeeee eee eeeeeeeee ee eee eeeeee: eeeeeeeeeee (8),[‌88‌] eeeeeeeeeeeee (8),[‌88‌] eeeeeeeeeee (8),[‌88‌] eee eeeeeeeeeee (8)[‌88‌] eee eeeeeeeeeeeeeeeee; eee eeeeeeeeeeeee eeeeeeeeee eeeeeeeeee (8) ee eeee ee ee eeeeeeeeeeeee, eeeeeeeeeeee, eee eeeeeeeeeeeeee eeeee.[‌88‌]

Meeeee 8 Meeeeeeeeee-Meeeeee Meee Meeeeeeee[‌88‌‌88‌]

References


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