A simple synthesis of 4‐chloro‐5‐hydroxy‐1 H ‐benzo[g]indoles | Zendy

Yi HyungWoo | Zendy; Cho Hyun In | Zendy; Lee KeeJung | Zendy

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A simple synthesis of 4‐chloro‐5‐hydroxy‐1 H ‐benzo[g]indoles

Author(s) -

Yi HyungWoo,

Cho Hyun In,

Lee KeeJung

Publication year - 2005

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.5570420123

Subject(s) - chemistry , stereochemistry , primary (astronomy) , medicinal chemistry , physics , astronomy

The reaction of methyl 2‐(3‐chloro‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl)propenoate ( 2a ) with primary amines gave 4‐chloro‐5‐hydroxy‐3‐methoxycarbonyl‐1 H ‐benzo[g]indoles 5a‐f as major compounds and 3‐methoxycarbonyl‐4,9‐dioxo‐2,3,4,9‐tetrahydro‐1 H ‐benzo[ f ]indoles 6a‐d as minor ones. Whereas the reaction of 3‐(3‐chloro‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl)‐3‐buten‐2‐one ( 2b ) with primary amines afforded the corresponding 1 H ‐benzo[g]indoles 5g‐i as major products and 3‐acetyl‐4,9‐dihydro‐4,9‐dioxo‐1 H ‐benzo[ f ]indoles 7g, h as minor products.

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