Synthesis of 1‐substituted‐2,3,4,9‐tetrahydro‐(2‐oxopropyl)‐1 H ‐pyrido [3,4‐ b ] indoles and their base‐catalyzed rearrangements to  N ‐ [2‐[2‐(1‐alkyl‐3‐oxobutenyl)‐1 H ‐indol‐3‐yl] ethyl]acetamides | Zendy

Bobowski George | Zendy

Premium

Synthesis of 1‐substituted‐2,3,4,9‐tetrahydro‐(2‐oxopropyl)‐1 H ‐pyrido [3,4‐ b ] indoles and their base‐catalyzed rearrangements to N ‐ [2‐[2‐(1‐alkyl‐3‐oxobutenyl)‐1 H ‐indol‐3‐yl] ethyl]acetamides

Author(s) -

Bobowski George

Publication year - 1983

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570200202

Subject(s) - chemistry , indole test , catalysis , alkoxide , cleavage (geology) , sodium ethoxide , medicinal chemistry , ring (chemistry) , stereochemistry , ethanol , base (topology) , bond cleavage , organic chemistry , mathematical analysis , mathematics , geotechnical engineering , fracture (geology) , engineering

The condensation of 1 H ‐indole‐3‐ethanamides, 1 , with 2,4‐pentanediones, 2 , gave enamines 3 . Acid catalyzed ring closure of 3 gave 1‐(1‐substituted‐2,3,4,9‐tetrahydro‐ (2‐oxopropyl) ‐1 H ‐pyrido [3,4‐ b ] indoles 4 . Subsequent N ‐acetylation yielded 5 which sequentially produced 2,3‐disubstituted indoles 6 and 7 resulting from CN bond cleavage after treatment with sodium alkoxide in ethanol. Controlled catalytic hydrogenation of the latter gave saturated derivatives 8 and 9 .

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research