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.

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. [ABSTRACT FROM AUTHOR]