Cyclisation of Benzo[B]Thiophen-3(2H)-One 1,1-Dioxide and 1,3-Indanedione into Novel Methylene Bridged Polycyclic Diazocines and Their Rearrangement into Spirocyclic Compounds

Tetrahedron Letters 2014
B. Cekavicus, B. Vīgante, M. Rucins, Aiva Plotniece, K. Pajuste, M. Petrova, Sergejs Beļakovs, G. Duburs, A. Soboļevs

Methylene bridged polycyclic diazocines 2a and 2b were obtained in reactions of 1,3-indanedione, or benzo[b]thiophen-3(2H)one-1,1-dioxide, or 2,2′-methylene derivatives 3a,b with paraformaldehyde and ammonia or hexamethylenetetramine in acidic medium. A structural revision of methylene bridged benzothieno-diazocine 2b based on results of X-ray diffraction analysis is presented. Internal rearrangement of methylene bridged polycyclic diazocines into spiroheterocycles 4a,b is also described

Atslēgas vārdi
Mannich reaction; Internal rearrangement; Structure revision; Spiroheterocycle; Methylene bridged polycyclic diazocine
DOI
10.1016/j.tetlet.2014.06.106
Hipersaite
http://www.sciencedirect.com/science/article/pii/S0040403914011198

Cekavicus, B., Vīgante, B., Rucins, M., Plotniece, A., Pajuste, K., Petrova, M., Beļakovs, S., Duburs, G., Soboļevs, A. Cyclisation of Benzo[B]Thiophen-3(2H)-One 1,1-Dioxide and 1,3-Indanedione into Novel Methylene Bridged Polycyclic Diazocines and Their Rearrangement into Spirocyclic Compounds. Tetrahedron Letters, 2014, Vol.55, Iss.33, 4601.-4604.lpp. ISSN 0040-4039. Pieejams: doi:10.1016/j.tetlet.2014.06.106

Publikācijas valoda
English (en)