Synthesis and [3+2] cycloaddition reaction of 3‐[(trimethylsilylmethylamino)(methylthio)‐methylene]heterocyclic compounds | Zendy

Tominaga Yoshinori | Zendy; Takada Satoshi | Zendy; Kohra Shinya | Zendy; Shigemitsu Yasumitsu | Zendy

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Synthesis and [3+2] cycloaddition reaction of 3‐[(trimethylsilylmethylamino)(methylthio)‐methylene]heterocyclic compounds

Author(s) -

Tominaga Yoshinori,

Takada Satoshi,

Kohra Shinya,

Shigemitsu Yasumitsu

Publication year - 2001

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.5570380519

Subject(s) - chemistry , methylene , trimethylsilane , oxindole , cycloaddition , amine gas treating , medicinal chemistry , organic chemistry , catalysis

3‐[(Trimethylsilylmethylamino)(methylthio)]methylene‐2‐coumaranone ( 4a ) and 1‐methyloxindole ( 4b ), readily prepared by reactions of the corresponding bis(methylthio)methylene heterocyclic compounds ( 2a, b ), with (trimethylsilylmethyl)amine (3), were found to be synthetic equivalents of heterocyclic alkylidene‐azomethine ylides. Reactions of 4a, b with reactive heterodipolarophiles such as aldehydes and ketones and reactive alkenes in the presence of cesium fluoride gave the 1,3‐dipolar cycloadducts, 3‐(2‐oxazoli‐dinylidene)‐oxindole and ‐coumaran‐2‐one derivatives ( 8a‐j, 9a‐h ), as well as pyrrolylidenecoumaran‐2‐one and oxindole derivatives ( 12‐15,17,18 ), via the 1,3‐elimination of (methylthio)trimethylsilane.

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