Process for the preparation of tricyclic-heterocycles

Details Process for the preparation of tricyclic-heterocycles Process for the preparation of tricyclic-heterocycles

1994-08-08

1995-07-25

Shah, Mukund J.

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

540576, 540577, 540578, 540587, C07D22320, C07D47104, C07D491048, C07D49504

Patent

active

054363330

ABSTRACT:
Compounds of the formula: ##STR1## in which R.sup.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, amino, bromo, chloro, fluoro, iodo, C.sub.1 -C.sub.3 alkylcarbonyl or trifluoromethyl; R.sup.2 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 --C.sub.3 alkoxy, bromo, chloro, fluoro, iodo, or C.sub.1 -C.sub.3 alkylcarbonyl; or R.sup.1 and R.sup.2 taken together are methylenedioxy or ethylenedioxy; the structure ##STR2## represents, as described in the specification, an ortho-fused phenyl moiety; an aromatic 5-membered heterocycle containing N, O, or S; or an aromatic 6-membered heterocycle containing N; all of which may be optionally substituted, are produced by reaction of ##STR3## where R.sup.3 is a masked aldehyde or carboxyl group, with 2-nitro-benzyl bromide followed by removal of the mask, reduction and cyclization.

REFERENCES:
Carey, F. A., et al., Advanced Organic Chemistry, Part B (New York, Plenum, 1990), pp. 480-481, 689, and 691.
March, J., Advanced Organic Chemistry, Reactions, Mechanisms, and Structure, (New York, Wiley, 1992), pp. 606-608 and 1216.
Negishi, E.-I., Organometallics in Organic Synthesis, (New York, Wiley, 1980), pp. 99 and 404-405.
Renfroe, B., et al., Azepines, Part I, Chemistry of Heterocyclic Compounds, vol. 43, (New York, Wiley, 1984), pp. 15, 16, and 68.
Greene, T. W., et al., Protective Groups in Organic Synthesis, (New York, Wiley, 1991), pp. 188-191, 265-266, and 270-272.

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