An NHC-catalyzed regio- and stereoselective Mannich/lactamization domino reaction of N-(benzothiazolyl)imines with α-chloroaldehydes has been developed. This new protocol provides a facile approach for the asymmetric synthesis of benzothiazolo-pyrimidinones and a pyrrolo[1,2-a]indolone in moderate to good yields (34-78%) and excellent stereoselectivities (87-99% ee, up to >20 : 1 d.r.).

Pyrazole-based β-aminonitriles and β-amino-carbaldehydes as bifunctional building blocks are introduced in a facile copper(II)-catalysed one-pot domino generation of multiple N-containing heterobi- and tricycles. This streamlined synthetic approach permits easy access to novel pyrazole-fused imidazo- and pyrimido[1,2-c]pyrimidinones and to pyrazolo[3,4-d]pyrimidinone species with isolated yield...

In the crystal structure of the title compound, C(36)H(39)FN(4)OS, the two fused rings of the thienopyrimidine system are coplanar. The 4-fluoro-phenyl ring is twisted with respect to the heterocyclic pyrimidinone ring by 67.21 (14)°. The piperidine ring shows a half-chair conformation. One of the n-butyl chains is disordered equally over two sites. The crystal packing is stabilized by C-H⋯O hy...

In the title compound, C(17)H(15)F(3)N(4)O(2), the dihedral angle between the trifluoro-meth-oxy-substituted benzene ring and the pyrimidinone ring is 45.1 (5)°, while that between the fused benzene ring and the pyrimidinone ring is 0.67 (1)°. Part of one of the benzene rings and its trifluoro-meth-oxy substituent are disordered over two positions of approximately equal occupancy (0.51:0.49). I...

The mol-ecular and crystal structures of the title compound, C(16)H(14)FN(3)O(2), are stabilized by intra-molecular N-H⋯O and inter-molecular O-H⋯O hydrogen bonds. The existence of non-classical intra-molecular C-H⋯N hydrogen bonds provides a dihedral angle between the fluoro-substituted benzene and pyrimidinone rings of 7.9 (1)°.

all-endo-3-amino-5-hydroxybicyclo[2.2.2]octane-2-carboxylic acid (13) and all-endo-5-amino-6-(hydroxymethyl)bicyclo[2.2.2]octan-2-ol (10) were prepared via dihydro-1,3-oxazine or g-lactone intermediates by the stereoselective functionalization of an N-protected derivative of endo-3-aminobicyclo[2.2.2]oct-5-ene-2-carboxylic acid (2). Ring closure of b-amino ester 4 resulted in tricyclic pyrimidi...

In the title mol-ecule, C(16)H(15)FN(4)O, the dihedral angle between the fluoro-substituted benzene ring and the pyrimidinone ring is 52.34 (7)°, while the dihedral angle between the fused benzene ring and the pyrimidinone ring is 3.30 (6)°. An intra-molecular N-H⋯N hydrogen bond may, in part, influence the conformation of the mol-ecule. In the crystal structure, inter-molecular N-H⋯N hydrogen ...

Thioxothienopyrimidinones, alkylthio- and arylalkylthiothienopyrimidinones, thienopyrimidinones, thienopyrimidines a thienopyrimidinedione and a thienotriazolo-pyrimidinone were prepared from 2-amino-3-carboethoxy-4,5-disubstituted thiophenes and 2-amino-3-cyano-4,5-disubstituted thiophenes via reactions with different reagents.

The asymmetric unit of the title compound, C(22)H(16)ClN(3)O(5), consists of two crystallographically independent mol-ecules. The fused rings of the imidazo[1,2-a]benzo[4,5]furo[3,2-d]pyrimidine system are nearly coplanar and the chlorophenyl rings are twisted with respect to the two pyrimidinone ring systems by 71.00 (2) and 62.59 (2)°. The C atoms of the ethyl side chain are disordered and we...