ES415678A1 - A procedure for the preparation of new derivatives of oxazolopiridinas. (Machine-translation by Google Translate, not legally binding) - Google Patents

Abstract

A procedure for the preparation of new oxazolopyridine derivatives of structural formula: **(See formula)** where the six-membered ring is a pyridine with nitrogen in one of the unsubstituted positions and where R is (see formula), where n is an integer from 1 to 5 and the X substituents are the same or different and represent: (1) halogen, (2) lower alkoxy, (3) lower alkyl, (4) nitro, (5) phenyl, (6) lower alkylsulfonyl, (7) trihaloalkyl (lower), (8) cyano, (9) lower alkyl guy, (10) carbamyl, (11) dialkyl (lower) amino, (12) lower alkyl amino, (13) lower alkyl sulfinyl, (14) mercapto, (15) trifluoromethoxy, (16) lower alkanoyloxy, (17) hydroxy, (18) alkanoyl (lower) amino, (19) amino, (20) benzoylamino, (21) halobenzoylamino, (22) lower alkyl benzoylamino, (23) lower alkoxy benzoylamino, (24) (see formula), where w is an integer from 1 to 3 and the substituents R2 are the same or different and represent hydrogen or lower alkyl, (25) **(See formula)** (26) **(See formula)** (27) **(See formula)** (28) -COOR2, (29) - (CH2) wcCOOR2 (30) - (CH2) wCN- (31) two X radicals on adjacent carbon atoms joined together to form a methylenedioxy group; (b) (see formula), where X and n are those previously defined (c) lower cycloalkyl; (d) a 5- or 6-membered heterocycle containing up to 2 heteroatoms selected from oxygen, nitrogen and sulfur; (e) naphthile; (f) adamantyl; R1 is (a) halogen, (b) lower alkyl, (c) nitro, (d) trihaloalkyl (lower), (e) amino, (f) benzoylamino, (g) lower alkoxy, (h) dialkyl (lower) amino, (i) alkyl (infericr) amino, (j) phenyl, (k) lower alkoxycarbonylamino, (l) cyano; and m is 0-2; with the proviso that R is not 4-halophenyl, 4-lower (alkyl) phenyl, 4-lower alkoxy phenyl, 4-nitrophenyl or 4-aminophenyl; whose procedure is to cycle with condensation two compounds of formulas: **(See formula)** where Z is -OH, halogen or (see formula) to produce a compound of formula: **(See formula)** where R3 is (a) (see formula), where n is an integer from 1 to 5; and the X substituents are the same or different and represent (1) halogen, (2) lower alkoxy, (3) lower alkyl, (4) nitro, (5) phenyl, (6) lower alkylsulfonyl, (7) trihaloalkyl (lower), (8) cyano, (9) lower alkyl guy, (10) dialkyl (lower) amino, (11) lower alkyl amino, (12) mercapto, (13) trifluoromethoxy, (14) hydroxy, (fifteen) (see formula), where R2 is hydrogen or lower alkyl or (15) two X radicals on adjacent carbon atoms bonded together to form a methylenedioxy group; (b) lower alkyl **(See formula)** (c) lower cycloalkyl, (d) naphthyl, (e) adamantanyl, (f) - (CH2) wCN9, or (g) a 5-6 membered heterocycle containing up to 2 heteroatoms selected from oxygen, nitrogen, and sulfur; R4 is (a) halogen, (b) lower alkyl, (c) nitro, (d) trihaloalkyl (lower) or (e) lower alkoxy; and m is 0-2 and, if desired: (a) When R3 is (see formula), where X is cyano, conversion of the cyano group to carbamyl, (see formula) or -COOR2; (b) when R3 is (see formula), where X is nitro, conversion of the nitro group to amino, followed by conversion to alkanoyl- (lower) amino, benzoylamino, halobenzoylamino, lower alkyl benzoylamino, lower alkoxy benzoylamino or (see formula); (c) when R3 is (see formula), where X is hydroxy, conversion of the hydroxy group to lower alkanoyloxy or to (see formula); (d) when R3 is (see formula), where X is lower alkyl thio, conversion of the lower alkyl thio group into a lower alkyl sulfinyl group; (c) when R3 is (see formula), where X is - (CH2) wCN, conversion of the group - (CH2) wCN into a group - (CH2) wCOOR2; (f) when R4m is nitro, conversion of the nitro group to amino, followed by conversion to benzoylamino, dialkyl- (lower) amino, lower (alkyl) amino, lower (alkoxy) -carbonylamino or phenyl; (g) when R4m is halogen, conversion of the halogen group to cyano; (h) when R3 (see formula), group conversion (see formula) (Machine-translation by Google Translate, not legally binding)