Derivatives of the thiazolo[2,3‐a]isoquinolinium system | Zendy

Andrew H. F. | Zendy; Bradsher C. K. | Zendy

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Derivatives of the thiazolo[2,3‐a]isoquinolinium system

Author(s) -

Andrew H. F.,

Bradsher C. K.

Publication year - 1966

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.5570030310

Subject(s) - chemistry , acetic anhydride , phthalimide , deprotonation , thio , medicinal chemistry , organic chemistry , ion , catalysis

The ketosulfides (IV) formed by the reaction of α‐bromoketones with 2α‐thiohomo‐phthalimide (II) have been cyclized to form hydrogen‐bonded, dimeric hemiperchlorates (V). Alternative products from the cyclization, 2‐[2′‐(carboxymethyl)phenyl]thiazoles (VII), may be cyclized with acetic anhydride to O ‐betaines (VI). The same betaines are obtained from the hemiperchlorates (V) by deprotonation. The ketosulfide hydrobromides (XIII) from α‐bromoketones and 1‐thio‐3, 4‐dihydroisocarbostyril (XII) give 5,6‐dihydro‐thiazolo[2,3‐a]isoquinolinium salts (XV) on cyclization.

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