Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Green and Efficient Construction of Chromeno[3,4-c]pyrrole Core via Barton-Zard Reaction from 3-Nitro-2H-chromenes and Ethyl Isocyanoacetate.

ABSTRACT: A regioselective one-pot method for the synthesis of 1-ethyl 2,4-dihydrochromene[3,4-c]pyrroles in 63-94% yields from available 2-phenyl-, 2-trifluoro(trichloro)methyl- or 2-phenyl-2-(trifluoromethyl)-3-nitro-2H-chromenes and ethyl isocyanoacetate through the Barton-Zard reaction in ethanol at reflux for 0.5 h, using K2CO3 as a base, has been developed.

SUBMITTER: Kochnev IA

PROVIDER: S-EPMC9737169 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Green and Efficient Construction of Chromeno[3,4-c]pyrrole Core via Barton-Zard Reaction from 3-Nitro-2H-chromenes and Ethyl Isocyanoacetate.

Kochnev Ivan A IA Barkov Alexey Y AY Zimnitskiy Nikolay S NS Korotaev Vladislav Y VY Sosnovskikh Vyacheslav Y VY

Molecules (Basel, Switzerland) 20221202 23

A regioselective one-pot method for the synthesis of 1-ethyl 2,4-dihydrochromene[3,4-c]pyrroles in 63-94% yields from available 2-phenyl-, 2-trifluoro(trichloro)methyl- or 2-phenyl-2-(trifluoromethyl)-3-nitro-2H-chromenes and ethyl isocyanoacetate through the Barton-Zard reaction in ethanol at reflux for 0.5 h, using K2CO3 as a base, has been developed. ...[more]

PMID: 36500555

Similar Datasets

2-Methyl-4-(naphthalen-2-yl)-3a-nitro-3,3a,4,9b-tetra-hydro-2H-spiro-[chromeno[3,4-c]pyrrole-1,3'-indolin]-2'-one.

Project description:In the title compound, C29H23N3O4, the 2-methylpyrrolidine ring adopts a twist conformation on the N-C bond involving the spiro C atom, while the hydropyran ring adopts an envelope conformation with the methine C atom bonded to the O atom as the flap. The mean plane of the indoline-2-one ring system is almost perpendicular to the mean plane of the pyrrolidine ring, making a dihedral angle of 89.73 (8)°. The latter ring makes dihedral angles of 47.80 (8) with the naphthalene ring system and 32.38 (8)° with the hydropyran ring mean plane. There is an intra-molecular C-H⋯O hydrogen bond involving the indoline-2-one O atom. In the crystal, adjacent mol-ecules are linked via N-H⋯O hydrogen bonds, forming chains propagating along [100]. The chains are linked via weak C-H⋯O hydrogen bonds, forming two-dimensional networks, lying parallel to (101), and consolidated by C-H⋯π inter-actions.

| S-EPMC3772478 | biostudies-literature

(3R,4S)-3,4-Isopropyl-idenedioxy-3,4-dihydro-2H-pyrrole 1-oxide.

Project description:The title compound C(7)H(11)NO(3) was prepared by intra-molecular nucleophilic displacement of 2,3-O-iso-propyl-idene-d-erythronolactol. There are two mol-ecules in the asymmetric unit, which are related by a pseudo-inversion centre. The crystal structure determination confirms unequivocally the configuration of the chiral centres as 3S,4R. In the crystal structure, inter-molecular C-H⋯O inter-actions link the mol-ecules (into infinite zigzag chains along the a axis.

| S-EPMC3089370 | biostudies-literature

(3R,4S)-3,4-Isopropylidenedioxy-5-phenylsulfonylmethyl-3,4-dihydro-2H-pyrrole 1-oxide.

Project description:The title compound, C(14)H(17)NO(5)S, was prepared by oxidation of (2R,3S,4R)-2-phenyl-sulfonyl-methyl-1-hy-droxy-3,4-iso-pro-pyl-idene-dioxy-pyrrolidine. Its crystal structure confirms unequivocally its configuration. Two inter-molecular C-H⋯O inter-actions help to establish the packing.

| S-EPMC3089343 | biostudies-literature

Ethyl 3,4-dimethyl-1H-pyrrole-2-carboxyl-ate.

Project description:The non-H atoms of the title compound, C(9)H(13)NO(2), are almost coplanar (r.m.s. deviation = 0.0358 Å). Weak inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into zigzag chains along the b axis with graph-set motif C(5). The chains are further linked into a three-dimensional network by C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

| S-EPMC3008020 | biostudies-literature

5-(3-Chloro-phen-yl)-2-phenyl-3,4-dihydro-2H-pyrrole.

Project description:In the title compound, C(16)H(14)ClN, the conformation of the five-membered ring approximates to an envelope with a C atom as the flap. The dihedral angle between the aromatic rings is 78.71 (9)°.

| S-EPMC3009276 | biostudies-literature

Ethyl 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxyl-ate.

Project description:The mol-ecule of the title compound, C(10)H(13)NO(3), is approximately planar (maximum deviation 0.1424 Å). In the crystal, mol-ecules are linked into inversion dimers by pairs of N-H⋯O hydrogen bonds, and the dimeric units are linked by non-classical C-H⋯O hydrogen bonds, forming a layered structure.

| S-EPMC2969404 | biostudies-literature

2,5-Dihexyl-3,6-diphenyl-pyrrolo-[3,4-c]pyrrole-1,4(2H,5H)-dione.

Project description:The asymmetric unit of the title compound, C(30)H(36)N(2)O(2), contains one half-mol-ecule, the other half being generated by a crystallographic inversion centre. The crystal structure is devoid of any classical hydrogen bonds however, non-classical C-H⋯O inter-actions link the mol-ecules into chains propagating in [001] and a C-H⋯π inter-action leads to the formation of a two-dimensional network in (011).

| S-EPMC3006905 | biostudies-literature

Metalloradical approach to 2H-chromenes.

Project description:Cobalt(III)-carbene radicals, generated through metalloradical activation of salicyl N-tosylhydrazones by cobalt(II) complexes of porphyrins, readily undergo radical addition to terminal alkynes to produce salicyl-vinyl radical intermediates. Subsequent hydrogen atom transfer (HAT) from the hydroxy group of the salicyl moiety to the vinyl radical leads to the formation of 2H-chromenes. The Co(II)-catalyzed process can tolerate various substitution patterns and produces the corresponding 2H-chromene products in good isolated yields. EPR spectroscopy and radical-trapping experiments with TEMPO are in agreement with the proposed radical mechanism. DFT calculations reveal the formation of the salicyl-vinyl radical intermediate by a metalloradical-mediated process. Unexpectedly, subsequent HAT from the hydroxy moiety to the vinyl radical leads to formation of an o-quinone methide intermediate, which dissociates spontaneously from the cobalt center and easily undergoes an endocyclic, sigmatropic ring-closing reaction to form the final 2H-chromene product.

| S-EPMC3936204 | biostudies-literature

3,3'-Ethyl-enebis(3,4-dihydro-6-chloro-2H-1,3-benzoxazine).

Project description:The asymmetric unit of the title compound, C(18)H(18)Cl(2)N(2)O(2), contains one half of an independent mol-ecule, the other half being generated via a centre of inversion at the mol-ecular centroid. In the crystal structure, mol-ecular chains are formed through non-classical C-H⋯ O hydrogen bonds between an axial H atom of the oxazine ring and the O atom of a neighbouring mol-ecule.

| S-EPMC2979041 | biostudies-literature

1-Methyl-3-(2-methyl-phen-yl)-3a-nitro-1,2,3,3a,4,9b-hexa-hydro-chromeno[4,3-b]pyrrole.

Project description:The asymmetric unit of the title compound, C(19)H(20)N(2)O(3), contains two independent mol-ecules in both of which the pyrrolidine ring adopts an envelope conformation, but with a C atom as the flap in one mol-ecule and the N atom in the other. The pyran ring adopts a half-chair conformation in both mol-ecules. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

| S-EPMC3379324 | biostudies-literature