TY - JOUR

T1 - Synthesis of spirocyclic tetrahydroisoquinolines (spiroTHIQs) via the Castagnoli-Cushman reaction

AU - Safrygin, Alexander

AU - Dar'in, Dmitry

AU - Bakulina, Olga

AU - Krasavin, Mikhail

PY - 2020/10/15

Y1 - 2020/10/15

N2 - A new route to privileged spirocyclic tetrahydroisoquinolines (spiroTHIQs) has been developed. The key step in which the spirocyclic system is formed in generally good yields and diastereoselectivity is the three-component Castagnoli-Cushman reaction of homophthalic anhydride, cyclic ketones and ammonium acetate. Decarboxylation of the initial adduct yields THIQ lactams which are reduced by lithium aluminum hydride. The route is shorter, more convergent and operationally simpler than the previously reported syntheses of similar spirocyclic building blocks.

AB - A new route to privileged spirocyclic tetrahydroisoquinolines (spiroTHIQs) has been developed. The key step in which the spirocyclic system is formed in generally good yields and diastereoselectivity is the three-component Castagnoli-Cushman reaction of homophthalic anhydride, cyclic ketones and ammonium acetate. Decarboxylation of the initial adduct yields THIQ lactams which are reduced by lithium aluminum hydride. The route is shorter, more convergent and operationally simpler than the previously reported syntheses of similar spirocyclic building blocks.

KW - Castagnoli-Cushman reaction

KW - Decarboxylation

KW - Lactam reduction

KW - Privileged structures

KW - Spirocycles

KW - Tetrahydroisoquinolines

KW - DESIGN

KW - INHIBITORS

UR - http://www.scopus.com/inward/record.url?scp=85090570800&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/54e76f06-54c8-3bc7-bd2b-f03dfce8e1e3/

U2 - 10.1016/j.tetlet.2020.152408

DO - 10.1016/j.tetlet.2020.152408

M3 - Article

AN - SCOPUS:85090570800

VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 42

M1 - 152408

ER -