0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via Isoquinolines

DOI: 10.1055/sos-SD-115-00651

Pilgrim, B. S.; Tucker, M. J.Science of Synthesis Knowledge Updates, (20191181.

Isoquinoline is a 10π-electron aromatic heterocycle, which was first isolated from coal tar in 1885. The systematic numbering of isoquinoline is shown in Scheme 1. Although the term isoquinoline formally refers to the fully aromatic system, it has come to be used more loosely when describing more saturated versions of the same framework (such as the di-, tetra-, and decahydroisoquinolines). This update will focus on the fully aromatic system but it will also feature selected examples of the synthesis of more reduced skeletons.

Meeeee 8 Meeeeeeeee Meeeeeeee ee Meeeeeeeeeee

Mee eeeeeeeeeeee eeeee eeeeee ee e eeeee eeeee ee eeeeeee eeeeeeee (eeee ee eeee ee eee 8,8,8,8-eeeeeeeeee eeeee), eeeee eeeeeee eeee eeeeeee ee eeeeeeeee eeeee ee eeeeeeeeee eeeeeeee (Meeeee 8). M eeeee eeeeee ee eeeeeeeee eeeeeeeeeee eee eeeeeeeeeeee eeeeeeeee.[‌8‌‌8‌] Meeeeee eeeeeeee eeeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeee eeeeeee eeeeeee eee eeeee eeeee eeeeeeeee eeee ee eeeeeeee (8) eee eeeeeeeeee (8; e eeeeee eeeeeeeeeee).[‌8‌] Meeeeeeeeee M (8), eeeeeeee eeee eee eeeeee ee Meeeeeeee eeeeeeeee,[‌8‌] eeeeeeee eeeeeeeeee eeeeeeeeeeee.[‌8‌] Meeeeeeeeee (8, eeee eeeee ee eeeeeeeeeeeee 888), eeeee eeeeeeee eeeee eeeeee eeeeeeeeeeee eeeeeeee, ee eeeeeeeee eeee eee eee eeeeee Meeeeeeeeeeee eeeeeeeee.[‌8‌] Mee ee eee eeeeeeeeee eeeeee eeee eee eee eeeeee, ee eee eeee e eeeeee eee eeee eeeee eeeeeeeee[‌8‌] eee eeeeeeeeeeeee eeeeeeeeee, eee eeeeee eeee eee eee eeeeeeeeeee ee eee eeee eee eee eeeeeeeee ee eeee eeeeee eeeeeee ee eeee ee eeeee eeeeeeeee eeeeeeee eeeeee. Meee eeeee eeeeeeeeeeee-eeeeeeeeee eeeeeee eeeeeeee eeee eeee eee eeeeee ee eeeee eeeeeeeee eeeeeeeee.[‌8‌,‌88‌] Mee eeeeeeee-eeeeeeeee eeeeee ee eee eeeeeeeeeeee eeee ee eeeee e eeeeeeeee eeeeeeee ee eeeeeeeeeeeeee eeeeee, eeeeeeeeeee eee eeeeeeee eeeeeee eeeeeeeee eeeeeeeeeee. Mee eeeeeeeeee eeeeeeeeeeeeee eeeeeeee eeeeee MM-88888 (8)[‌88‌] eeeeeeee e eeeee eeeeeeee eeeeeeeeeeee, eee eeeeeeeee (8), eeeee ee eeee ee eee eeeeeeeee ee eeeee eeeeeee eee eeeeeeeeeeee,[‌88‌] e eeeeeeeeeeeeeeeeeeeeee. Meeeeeeeeeeee eeee eeee eeee eeeeeeee ee eeeeeeeee eeeeeeeeee ee 88β-MMM8,[‌88‌] eeee-MMM eeeeeeeee,[‌88‌] eeeeeeee eeeeeeee/eeeeeeeeeee,[‌88‌] eee eee-eeeeeee eeeeeeee.[‌88‌]

Meeeee 8 Meee Meeeeeeeeeee-Meeeeeeeee Meeeeee Meeeeeee eee Meeeeeeeeeeeeee[‌8‌,‌8‌,‌8‌,‌88‌,‌88‌]

Meee eeeeeeee, eeeeeeeeeeee eeeeeeeeeee eeee eeeee eeeeeeeeeee eeeeeee ee eee eeeeeeeeeeeeee eeeeeeee. Meeeeee eeeee eeeeeeeee ee eeeeeeeeeeeee eeeeeee e eee eeeeeeeeeeeeeee, eeeee eee eeeee eee ee eeeeeee eeeee-eeeeeeee eeeeee. Meeee eeeeeeeee, eeee ee eeee(8-eeeeeeeeeeeeeeeeee-M8,M)eeeeeee(MMM) (8), eeeeeee eee ee eeeee eeeeeeeeeeeeee eeeeeeeeeeee eeeee eeeeee e eeeeeee eeeeeee eeee (Meeeee 8).[‌88‌‌88‌] Meeeeeeeeeee-eeeeeeeeee eeeeeee eeee eeee eeeee eeeeeee ee eeeeeeeee eeeeeeeeee eeeeeeeee,[‌88‌] eeee eee eeeeee (M)-8-[8-(eeeeeeeeeeeeeeeee)eeeeeeeeee-8-ee]eeeeeeeeeeee [8, (M)-MMMMMM; Meeeee 8],[‌88‌,‌88‌] eee eeeeeee, eeeee eeeeeeee ee eeeeeeeeeeeeeee eeee ee 8,8-eeeeeee eeeeeeeeeeeeee[‌88‌] eee eeeeee eeeeeeee ee eeeeeeee.[‌88‌] Meeeeeeeeeeee (e.e., 8) eeee eeee eeee eeeeeeee ee eeeeeee eee eeeeeeeeee eeee (Meeeee 8). Mee eeeeeeeee eeeeee eeee eeeeeeeeeee eeee ee eeeeeeeeee(MMM), eeeeeeeee(MMM), eee eeeeeeeee(MMM) eee eee eeee ee eeee-eeeeeeee eeeeeee eeeeee eee eeeeeeee eeeeeeeee eeeeeee (MMM) eeeeeeee eeeeee, eeee eeeeeeeeee eeee eee ee eeeeee ee eeeeeeeeeee eee eeeeeeeeeeee eeeeeeee ee eee eeeeeeeeeeee.[‌88‌]

Meeeee 8 Meeeeeee ee Meeeeeeeeeee-Meeeeeeeee Meeeeeeeee Meeeeee Meeeeeeee[‌88‌‌88‌,‌88‌,‌88‌,‌88‌]

Meee eeeeeeee eee eee eeeeee eeeeeeeee, eeeeeeeeeeee ee eeeeee eeeee (eMM 8.8),[‌88‌] eee eeeeeeeeeee ee eeee eee eeeeeeeeeeeeee eeeeee eeeeeeeee eee 8M MMM eeeeeeee eeeeee ee eeee ee eeeeeee e eeeeeeeeeeee eeeee ee eee MM eeeeeeeeee eeeeeeee. Mee eeeeeeeeee eeeeeee ee eeeeeeeeeeeee eeee eeeeeee eeeeeee eeee ee eeeeeeeee eee eeeeeeeeee. Mee eeeeeeeeeeee eeee, eeeee ee eeeeeeeeeeeee eeee eeeeeeee-eeeeeeeee eeee eee eeeeeeeeeee eeee, ee eeeeeee eeeeeeee ee eeeeeeeeeeee, eeee eeeeee ee eee M8 eeeeeeee eeeeeeeee eeeeeee. Mee eeeeeeeeee ee eeeeeee eeeee ee eee eeeeeeeeeeee eeee ee ee eeeeeeeee ee eeeeeeeeeeee eeeeeeeeeeee eeeeee eeeeeee, eeee eeeee ee M8 eeeee eeeeee eeeeee, eeeee ee M8 eeeeeeeeeeee ee eeeeeeeeee, eee eeeee ee M8 eeeeeeee ee ee e eeeeeeee eeeeeeeeeee.[‌88‌] M eeeeeee eeeeeee ee eeeeeee eeeeeeeeee ee eeee eeeeeeee eeee eeeeeeeeeeeeeeee eeeeeeeeeee ee eeeeeeeee(8)-eeeeeeeee eeeeeeeee.[‌88‌,‌88‌] Mee eeeeeeee-eeeeeeeee eeeeee ee eee eeeeeeeeeeee eeeee eeeeeeeee eeee eeeeeeeeeeeee eeeeeeeee eeeeeeee. Meee e eeeeeeee eeee eeeee eeeee, ee eeeeee eeeeeeeeeeeee ee eee eeee eeeeeeee-eeeeeeeee eeeeeeeeeee eeee ee M8, eeee eeee eeee eeeeeeeeee ee M8.[‌88‌,‌88‌]

Me eee eeeeeeeeeeee eeeeeeeeeee, eeeeeeeeeeee 8-eeeeee (ee M-eeeeee) eee eeeeeee eee eeee eeeeeeeee. Mee eeeeeeee ee eee M-eeeee eeee eee eeeeeee eeeeeeeeee eeee eeee eeeeeeeeeeee eee eeeeeeeeeeeee eee eeeee ee M-eeeee ee e eeeeeeee eeeeeeee eeeeeeee eee eee eeeeeeeeeee eeeeeeeeeeee ee ee eeeeeeeeeeee eeee. Meeeeeeeeeee 8-eeeeee eeee eeee eeeee eeeeeeeeee ee e eeeeeeeee eeeee eee MM eeeeeeeeeeeeeeeee eeeeeeeee, eeeeeee ee e eeeeeeeeee ee eeeeeeee ee eeee eeeee. Meeeeeeeeeee 8-eeeeee eee ee eeeeeee eeeeeeee eeee eee eeeeee eeeeeeeeeeee eeee e eeeee ee eeeeeeeee eeeeee. Meeeeee, eeee eeeeeeee eeeeeee eeeeee eeeeeeeee eeeeee eeee eeee eeeeeeeee eeee eeeeeeee eeeeeee eeeeeeeeee MM eeeee. Mee eeeeeeeee ee eeeeeeeeeeee 8-eeeeee ee eeeeeeeee eeeeeeeeee ee Meeeeee Mee eeeee eeeeeeeee eeeee ee eeeeeeeeeee eee eeeeeeeeeeeeee eeeee, eeeee eee eeeeeeeee eeeeeeeeee ee Meeeeee Meee eee eeeeeeee eeeeee eeee eee eeeeee eeeeeeeeeeee ee eeeeeeee ee eee eeeeeeee eeee eeee eeee eeeeeeee eeeeeeeeeeeee, eeeeeeee eeee eee eeee ee eeeeeeee eeeeeeeeeee eee.

Me eeee ee eeee eeeeeee ee eee eeeee eeeeee ee eeeeeeeeeeeee ee Meeeeee ee Meeeeeeee, eee eeeeeeeee ee eeeeeeeeeeeee eee eeee eeeeeeee eeeeeee ee eeeeeee eeeeeeeee, eeeeeeeee eeeeeeee ee Meeeeeeeeeee Meeeeeeee[‌88‌] eee Meeeeeee ee Meeeeeeeeeee Meeeeeeee,[‌88‌] ee eeeee eeeeeee eee eeeeeeee eee eeee eeeeeeeeeee.