Process for cyclization

Details Process for cyclization Process for cyclization

1981-05-18

1982-06-15

Raymond, Richard

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen in the nitrogen containing substituent

C07D49802

Patent

active

043352405

ABSTRACT:
Azetidinone alcohol disulfides are synthesized by reduction of the corresponding aldehydes. The azetidinone alcohol disulfides are the substrates for a process which cyclizes these compounds to 1-oxa .beta.-lactam compounds, employing a cyclizing reagent chosen from the class consisting of divalent mercury salts or tri-valent phosphine compounds. The 1-oxa .beta.-lactam compounds produced by this process are intermediates in the synthesis of 1-oxa .beta.-lactam antibiotics.

REFERENCES:
patent: 3872086 (1975-03-01), Barton et al.
patent: 3954732 (1976-05-01), Kamiya et al.
patent: 4024152 (1977-05-01), Kukolja
patent: 4066641 (1978-01-01), Hamashima et al.
patent: 4071513 (1978-01-01), Kim
Barton et al., Chem. Comm., (1971), p. 1137.
Kamiya et al., Tet Letters (1973), p. 3001.
Kim et al., Tet Letters (1978), p. 409.
Masamure et al., J. Amer. Chem. Soc., vol. 97 (1975), p. 3515.
Wolfe et al., Can. J. Chem., vol. 52 (1974), p. 3996.
Naylor et al., The Chemical Society, London, 1977, pp. 204-213.
Narisada et al., Heterocyclics, vol. 7 (1977), pp. 839-849.

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