Synthesis of 1,2‐five‐ring‐annellated barrelenes  via  the intramolecular  Diels ‐ Alder  reaction of acetylenic derivatives | Zendy

Trifonov Latchezar S. | Zendy; Orahovats Alexander S. | Zendy

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Synthesis of 1,2‐five‐ring‐annellated barrelenes via the intramolecular Diels ‐ Alder reaction of acetylenic derivatives

Author(s) -

Trifonov Latchezar S.,

Orahovats Alexander S.

Publication year - 1987

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19870700708

Subject(s) - chemistry , intramolecular force , diels–alder reaction , isocyanate , ring (chemistry) , cleavage (geology) , intramolecular reaction , medicinal chemistry , stereochemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering , polyurethane

The intramolecular Diels‐Alder reaction conducted with acetylenic acylureas, obtained from carbodiimides, and the acetylenic acid 5 and its derivatives 13 gave the 1,2‐annellated barrelene 14 (from 13a ) and the benzobarrelenes 8 (from 5 ) and 15 (from 13b ); in the case of 3‐butynoic acid ( 1 ),[1,3]‐H shift were observed. The formation of the azabarrelenes 16 (from 13c ) as an intermediate is postulated which looses HCN to afford the indolinone 17 . The acylureas 6 and 9 underwent isocyanate cleavage instead of [4+2] cyclization.

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