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Synthesis of new pentacyclic diquinothiazines
Author(s) -
Nowak Małgorzata,
Pluta Krystian,
Suwińska Kinga,
Straver Leo
Publication year - 2007
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.5570440307
Subject(s) - chemistry , thiazine , ring (chemistry) , derivative (finance) , alkylation , alkyl , medicinal chemistry , aryl , salt (chemistry) , stereochemistry , substrate (aquarium) , liquid ammonia , sodium salt , ammonia , organic chemistry , catalysis , oceanography , financial economics , economics , geology , inorganic chemistry
Reactions of 2,2′‐dichloro‐3,3′‐diquinolinyl sulfide 1 with ammonia derivatives and various primary alkylamines and arylamines proceeded as a thiazine ring closure to form linear annulated pentacyclic 6 H ‐diquinothiazine 2H and 6‐substituted derivatives 2 with alkyl, alkylaryl, aryl and heteroaryl substituents in moderate to good yields. Reaction with 2‐chloroethylamine did not stop at the formation of half‐mustard derivative 2k but ran to ethylenediquinothiazinium salt 11 . 6 H ‐Diquinothiazine 2H was N ‐alkylated and N ‐arylated to give 6‐substituted derivatives 2 . The crucial substrate 1 was obtained from other heteropentacenes 3 and 4 via 1,4‐dithiin ring opening and further transformations. X‐ray analysis of p ‐nitrophenyldiquinothiazine 2i revealed unexpected planar thiazine ring.