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Preparation and Some Reactions of 1H-1,4-Benzothiazine Ylides (= 1H-1,4-Benzothioniaazin-4-ide)

✍ Scribed by George M. Iskander; Ibrahim E. Khawad; Ghariballa Yousif; Keith Fisher; C. Kay Fair; Elmer O. Schlemper

Publisher
John Wiley and Sons
Year
1985
Tongue
German
Weight
431 KB
Volume
68
Category
Article
ISSN
0018-019X

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✦ Synopsis

A series of fifteen IH-1,4-benzothiazine ylides were obtained by alkylation of the corresponding 4H-1,4-benrothiazines 1. Ylides of type 2 g ~ r showed slight [I, 21 rearrangements upon thermolysis besides main dealkylation to 1 and olefin production. The ylides of this type underwent redox reactions when treated with hydrdzine hydrate alone, giving 3,4-dihydro-2H-1,4-benzothiazines mainly, while ylides of type 2a-f failed to react.

Syntheses.

~ Recently, we have investigated possible routes to the formation of some lH-l,4-benzothiazines ylides 2 [I]. Two routes were established: the cyclodehydration of the precursor sulfoxides 3 and direct alkylation of 4H-1,4-benzothiazines 1. We now have explored the second as a general route to an easy synthesis of these cyclic ylides. Fifteen new ylides 2 were prepared and their physical data recorded (Tables and). The ylides 2 were isolated as crystalline solids except for a few, obtained as oils and characterised as

CMe,CH,C(O), R' = Et i R', R2 = CH2CMe2CH2C(0), R' = Pr j R', R2 = CH,CMe,CH,C(O), R' = i-Pr k R', R2 = CH

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